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Format: 1 online resource (352 pages)

ISBN: 0-12-823746-5

Content: Photochemistry of Heterocycles is a comprehensive review of the topic, including photooxidation, photoreduction and photoaddition reactions as well as industrial aspects of heterocyclic photochemistry. Many materials used for the manufacturing of OLEDs and other electrooptical switches contain heterocycles, and the use of small molecules or polymers containing heterocyclic substances are being studied as new photovoltaic materials. This reference is ideal for synthetic organic chemists, specifically researchers working in organic photochemistry, as well as medicinal chemists and material scientists. Heterocyclic compounds are widely used in the modern world, and most of the drugs currently in use have heterocyclic nuclei among their constituents. These compounds are subject to a photochemical degradation processes which must be known and prevented.

Note: Front Cover -- Photochemistry of Heterocycles -- Copyright Page -- Contents -- Preface -- 1 Photochemical synthesis of heterocyclic compounds -- 1.1 Introduction -- 1.2 Azetidines -- 1.2.1 Synthesis by aza Paternò-Buchi reaction -- 1.2.2 Synthesis by intramolecular closure of N-formil-α-oxoamides -- 1.2.3 Synthesis by Norris-Yang rearrangement -- 1.2.4 Reaction between fullerene and formamidines -- 1.2.5 Synthesis by ciclization of amino ketones -- 1.3 Aziridines -- 1.3.1 Synthesis by rearrangement of pyridinium salts -- 1.3.2 Synthesis by insertion of nitrene into double bonds -- 1.3.3 Synthesis from homoallylpyrroles -- 1.3.4 Synthesis by rearrangement of triazolines -- 1.3.5 Synthesis of aziridines by visible-light induced decarboxylative cyclization of N-aryl glycines and diazo compounds -- 1.3.6 Photoinduced aziridination of alkenes with N-sulfonyliminoiodinane -- 1.3.7 Photochemical aziridination of fullerenes -- 1.3.8 Synthesis from sugar derivatives and azides -- 1.3.9 Synthesis from azides by photocatalysis -- 1.3.10 Synthesis from azidoformates -- 1.4 Diazepines and benzodiazepines -- 1.4.1 Synthesis from 4-pyridyl azides -- 1.5 Furans -- 1.5.1 Furans from α-bromo-β-dicarbonyl compounds and alkynes -- 1.5.2 Benzofurans from 2-chlorophenols and alkynes -- 1.5.3 Dihydro and tetrahydrofurans from cyclopropane derivatives -- 1.5.4 Dihydrofuran from photodimerization of β-carbonyl ketones -- 1.5.5 Tetrasubstituted furans from silylenolethers and α-bromo diketones -- 1.5.6 Synthesis of 5H-furanones from substituted cyclobutenones -- 1.5.7 Photochemical catalytical synthesis of dihydrofurans from vinyl and aryl cyclopropanes -- 1.5.8 Tetrahydrofurans from cyclobutanones and nitrile compounds -- 1.5.9 Reaction of propargyl derivatives with alkenes -- 1.5.10 Tetrahydrofurans from α,β-unsaturated ketones. , 1.5.11 γ-Lactones from allylic alcohols and α,β-unsaturated keto ester -- 1.5.12 Synthesis from cinnamic acid and ketones -- 1.5.13 Synthesis from α-chloro alkyl ketones and styrenes -- 1.5.14 Synthesis by isomerization of alkenes -- 1.6 Imidazoles and derivatives -- 1.6.1 Synthesis of an imidazole intermediated by HCN -- 1.6.2 Synthesis of dihydroimidazoles from pyridinium salts and an alkene -- 1.6.3 Synthesis of an imidazolinone by cyclization of a linear compound -- 1.6.4 Synthesis of purines by irradiation of urea/acetylene -- 1.6.5 One pot synthesis from aldehydes, α-aminonitriles and isoxazoles -- 1.6.6 Reaction of N-(1-methylpyrimidin-2-one)pyridinium chloride. Contraction to an imidazolidinone -- 1.7 Synthesis of oxadiazoles -- 1.7.1 1,2,4 Oxadiazoles from 2H-azirines and nitrosoarenes -- 1.7.2 Photooxidation of N-acylhydrazones to 1,3,4-oxadiazoles -- 1.8 Synthesis of oxazoles and related systems -- 1.8.1 Synthesis of oxazoles by conversion of 1-acyl triazoles -- 1.8.2 Synthesis from α-bromoketones and benzylamines -- 1.8.3 Three components condensation of silylenolethers, fluoroalkyl halides and chiral aminoalcohols to obtain oxazolidines -- 1.8.4 Oxazolidinones from propargylic amines and CO2 -- 1.8.5 Conversion of benzoil formamides to oxazolidin 4-ones -- 1.8.6 Synthesis of phosphonium substituted oxazoles from phosphonium-iodonium ylides -- 1.8.7 Synthesis from azirines and aldehydes -- 1.9 Oxetanes: the Paternò Büchi reaction -- 1.9.1 Exo-oxetanes from carbonyl compounds with vinylene carbonates -- 1.9.2 Photocycloaddition of N-acyl enamines to aldehydes -- 1.9.3 Oxetanes from carbonyl compounds and 2,5 dimethyl-4-isobutyl-oxazoles -- 1.9.4 Reaction of 2,3-dihydrofuran -- 1.9.5 Reaction of a silyl derivative of cinnamyl alcohol -- 1.9.6 Reaction of geraniol derivatives -- 1.9.7 Reaction with isoxazole derivatives. , 1.9.8 Synthesis of an elusive oxetane by photoaddition of benzophenone to thiophene in the presence of a Lewis acid -- 1.9.9 Reaction of 2-furylmethanol derivatives -- 1.9.10 Reaction of silyl enol ethers -- 1.10 Piperidines -- 1.10.1 Iodine catalyzed sp3-H amination -- 1.10.2 Synthesis from 2,6-diaminopimelic acid to piperidine-2,6-dicarboxylic acid -- 1.10.3 A photochemical reaction in the synthesis of azasugar derivatives -- 1.10.4 Piperidines from ring-contaction of N-chlorolactams -- 1.10.5 Synthesis of 2-piperidinone catalyzed from a hydrophobic analog of vitamin B12 -- 1.11 Pyrazoles -- 1.11.1 Aromatization of 1,3,5 trisubstituted pyrazolines -- 1.11.2 Photochemical bromination for preparation of mono, bis and fused pyrazole derivatives -- 1.11.3 Pyrazoles from hydrazines and Michael acceptors -- 1.11.4 Synthesis of pyrazole derivatives via formal [4+1] annulation and aromatization -- 1.11.5 Reaction of hydrazones and α-bromoketones -- 1.11.6 One pot synthesis of pyrazoles from alkynes and hydrazines -- 1.11.7 Sunlight-promoted direct irradiation of N-centered anion: the photocatalyst-free synthesis of pyrazoles -- 1.11.8 Efficient photooxidation of aryl (hetaryl)pyrazolines by benzoquinone -- 1.11.9 Synthesis of pyrazoles via photochemical ring opening of pyridazine N-oxides -- 1.12 Pyridines -- 1.12.1 Pyridines from ring closure of acyloximes -- 1.12.2 Synthesis of naphthyl pyridines from heptadynes and nitriles -- 1.12.3 Synthesis of substituted pyridine from aryl ketone and benzylamines -- 1.12.4 Pyridines from trimerization of two alkenes and a nitrile -- 1.13 Pyrimidines -- 1.13.1 Synthesis of benzo-fused pyrimidines- 4-ones from 1,2,4 oxadiazoles -- 1.13.2 Fluoroalkylates pyrimidines from silyl enol ethers, amidines, and fluoroalkylhalides. , 1.13.3 Three component synthesis from active methylene compounds, perfluoroalkyl iodides and guanidines -- 1.13.4 Synthesis of pyrimidones from 4-allyl-tetrazolones -- 1.14 Pyrroles -- 1.14.1 Dehydrogenative aromatization and sulfonylation of pyrrolidines -- 1.14.2 Synthesis of nitrogen heterocycles generated from α-silyl secondary amines under visible light irradiation -- 1.14.3 Synthesis of substituted pyrroles by dimerization of acyl azirines -- 1.14.4 Photochemical isomerizations of N-substituted 2-halopyrroles: syntheses of N-substituted 3-halopyrroles -- 1.14.5 Synthesis of pentacycles incorporating a pyrrole unit -- 1.14.6 Synthesis of 1,3,4 trisubstituted pyrroles by condensation of aryl azides and aldheydes -- 1.15 Pyrrolidines -- 1.15.1 Pyrrolydinones from suitable amides and an iridium catalyst -- 1.15.2 [3 + 2] Cycloaddition between a cyclopropylketone and an imine -- 1.15.3 Synthesis of pyrrolidines from alkanes and nitrogen derivatives -- 1.15.4 Aroylchlorination of 1,6 dienes to obtain 2-pyrrolidinones -- 1.15.5 Synthesis of pyrrolidinones fused with a cyclobutane ring -- 1.16 Thiophenes and benzothiophenes -- 1.16.1 Cyclization of 2-alkynylanilines with disulfide to afford benzothiophenes -- 1.16.2 Cyclization of diethynil sulfide to thiophene -- References -- 2 Photoisomerization of heterocyclic compounds -- 2.1 Photoisomerization of pentaatomic heterocycles -- 2.1.1 Isomerization of furan derivatives -- 2.1.1.1 Furan -- 2.1.1.2 Methylfurans -- 2.1.1.3 Alkylfurans -- 2.1.1.4 Trimethylsilyl-substituted furans -- 2.1.1.5 Furans bearing electron-donating or electron-withdrawing groups -- 2.1.2 Isomerization of pyrrole -- 2.1.3 Isomerization of thiophene -- 2.1.3.1 Alkylthiophenes -- 2.1.3.2 Arylthiophenes -- 2.1.3.3 Cyanothiophenes -- 2.1.3.4 Other thiophenes -- 2.1.4 Isomerization of isoxazole. , 2.1.4.1 Isoxazoles bearing electron-donating groups -- 2.1.4.2 Isoxazoles bearing electron-withdrawing groups -- 2.1.4.3 Benzisoxazoles -- 2.1.4.4 Isoxazolidones -- 2.1.5 Isomerization of oxazole -- 2.1.6 Isomerization of pyrazole -- 2.1.7 Isomerization of imidazole -- 2.1.8 Isomerization of thiazoles -- 2.1.8.1 Aryl-substituted thiazoles -- 2.1.8.2 Bithiazoles -- 2.1.8.3 Trithiazoles -- 2.1.8.4 Benzothiazole -- 2.1.9 Isomerization of isothiazoles -- 2.1.9.1 Benzoisothiazole -- 2.1.10 Isomerization of oxadiazoles -- 2.1.10.1 1,2,4-Oxadiazoles -- 2.1.10.2 1,2,5-Oxadiazoles -- 2.1.11 Other pentaatomic heterocycles -- 2.2 Photoisomerization of hexatomic heterocycles -- 2.2.1 Isomerization of pyridines -- 2.2.1.1 Pyridines -- 2.2.1.2 Dihydropyridine -- 2.2.1.3 Pyridinium salts -- 2.2.1.4 Pyridinium ylides -- 2.2.1.5 Pyridinium oxide -- 2.2.1.6 Quinolines and isoquinolines -- 2.2.2 Isomerization of diazines -- 2.2.2.1 Pyrazine -- 2.2.2.2 Pyridazine -- 2.2.2.3 Pyrimidine -- 2.2.2.4 Other compounds -- References -- 3 Photochemical behavior of diheteroarylethenes and photochromism -- 3.1 Photochemistry of olefins: An overview -- 3.2 Photoinduced pericyclic reactions: Stilbene and its diheteroarylethenes derivatives -- 3.2.1 Some applications of the Mallory reaction -- 3.3 The [2+2] photocycloaddition reactions on heteroarylethenes -- 3.4 Photochromism of diheteroarylethenes -- 3.4.1 A brief historical overview and basic reaction mechanism -- 3.4.2 Photochromism: Tuning with ethene bridges -- 3.4.3 Photochromism: Tuning with funtionalised heteroaryl groups -- 3.4.4 Photocyclization reactions and solvent effect -- 3.4.5 Photochromism in chiral diheteroarylethenes -- 3.4.6 Ring closure processes induced by visible radiation and all-visible photochromism -- 3.5 Applications of photochromic molecules of diheteroarylethenes: Switches and optical memories. , 3.5.1 Switches.

Additional Edition: Print version: D'Auria, Maurizio Photochemistry of Heterocycles San Diego : Elsevier,c2022 ISBN 9780128237458

Language: English

UID:

Format: 1 online resource (352 pages)

ISBN: 0-12-823746-5

Content: Photochemistry of Heterocycles is a comprehensive review of the topic, including photooxidation, photoreduction and photoaddition reactions as well as industrial aspects of heterocyclic photochemistry. Many materials used for the manufacturing of OLEDs and other electrooptical switches contain heterocycles, and the use of small molecules or polymers containing heterocyclic substances are being studied as new photovoltaic materials. This reference is ideal for synthetic organic chemists, specifically researchers working in organic photochemistry, as well as medicinal chemists and material scientists. Heterocyclic compounds are widely used in the modern world, and most of the drugs currently in use have heterocyclic nuclei among their constituents. These compounds are subject to a photochemical degradation processes which must be known and prevented.

Note: Front Cover -- Photochemistry of Heterocycles -- Copyright Page -- Contents -- Preface -- 1 Photochemical synthesis of heterocyclic compounds -- 1.1 Introduction -- 1.2 Azetidines -- 1.2.1 Synthesis by aza Paternò-Buchi reaction -- 1.2.2 Synthesis by intramolecular closure of N-formil-α-oxoamides -- 1.2.3 Synthesis by Norris-Yang rearrangement -- 1.2.4 Reaction between fullerene and formamidines -- 1.2.5 Synthesis by ciclization of amino ketones -- 1.3 Aziridines -- 1.3.1 Synthesis by rearrangement of pyridinium salts -- 1.3.2 Synthesis by insertion of nitrene into double bonds -- 1.3.3 Synthesis from homoallylpyrroles -- 1.3.4 Synthesis by rearrangement of triazolines -- 1.3.5 Synthesis of aziridines by visible-light induced decarboxylative cyclization of N-aryl glycines and diazo compounds -- 1.3.6 Photoinduced aziridination of alkenes with N-sulfonyliminoiodinane -- 1.3.7 Photochemical aziridination of fullerenes -- 1.3.8 Synthesis from sugar derivatives and azides -- 1.3.9 Synthesis from azides by photocatalysis -- 1.3.10 Synthesis from azidoformates -- 1.4 Diazepines and benzodiazepines -- 1.4.1 Synthesis from 4-pyridyl azides -- 1.5 Furans -- 1.5.1 Furans from α-bromo-β-dicarbonyl compounds and alkynes -- 1.5.2 Benzofurans from 2-chlorophenols and alkynes -- 1.5.3 Dihydro and tetrahydrofurans from cyclopropane derivatives -- 1.5.4 Dihydrofuran from photodimerization of β-carbonyl ketones -- 1.5.5 Tetrasubstituted furans from silylenolethers and α-bromo diketones -- 1.5.6 Synthesis of 5H-furanones from substituted cyclobutenones -- 1.5.7 Photochemical catalytical synthesis of dihydrofurans from vinyl and aryl cyclopropanes -- 1.5.8 Tetrahydrofurans from cyclobutanones and nitrile compounds -- 1.5.9 Reaction of propargyl derivatives with alkenes -- 1.5.10 Tetrahydrofurans from α,β-unsaturated ketones. , 1.5.11 γ-Lactones from allylic alcohols and α,β-unsaturated keto ester -- 1.5.12 Synthesis from cinnamic acid and ketones -- 1.5.13 Synthesis from α-chloro alkyl ketones and styrenes -- 1.5.14 Synthesis by isomerization of alkenes -- 1.6 Imidazoles and derivatives -- 1.6.1 Synthesis of an imidazole intermediated by HCN -- 1.6.2 Synthesis of dihydroimidazoles from pyridinium salts and an alkene -- 1.6.3 Synthesis of an imidazolinone by cyclization of a linear compound -- 1.6.4 Synthesis of purines by irradiation of urea/acetylene -- 1.6.5 One pot synthesis from aldehydes, α-aminonitriles and isoxazoles -- 1.6.6 Reaction of N-(1-methylpyrimidin-2-one)pyridinium chloride. Contraction to an imidazolidinone -- 1.7 Synthesis of oxadiazoles -- 1.7.1 1,2,4 Oxadiazoles from 2H-azirines and nitrosoarenes -- 1.7.2 Photooxidation of N-acylhydrazones to 1,3,4-oxadiazoles -- 1.8 Synthesis of oxazoles and related systems -- 1.8.1 Synthesis of oxazoles by conversion of 1-acyl triazoles -- 1.8.2 Synthesis from α-bromoketones and benzylamines -- 1.8.3 Three components condensation of silylenolethers, fluoroalkyl halides and chiral aminoalcohols to obtain oxazolidines -- 1.8.4 Oxazolidinones from propargylic amines and CO2 -- 1.8.5 Conversion of benzoil formamides to oxazolidin 4-ones -- 1.8.6 Synthesis of phosphonium substituted oxazoles from phosphonium-iodonium ylides -- 1.8.7 Synthesis from azirines and aldehydes -- 1.9 Oxetanes: the Paternò Büchi reaction -- 1.9.1 Exo-oxetanes from carbonyl compounds with vinylene carbonates -- 1.9.2 Photocycloaddition of N-acyl enamines to aldehydes -- 1.9.3 Oxetanes from carbonyl compounds and 2,5 dimethyl-4-isobutyl-oxazoles -- 1.9.4 Reaction of 2,3-dihydrofuran -- 1.9.5 Reaction of a silyl derivative of cinnamyl alcohol -- 1.9.6 Reaction of geraniol derivatives -- 1.9.7 Reaction with isoxazole derivatives. , 1.9.8 Synthesis of an elusive oxetane by photoaddition of benzophenone to thiophene in the presence of a Lewis acid -- 1.9.9 Reaction of 2-furylmethanol derivatives -- 1.9.10 Reaction of silyl enol ethers -- 1.10 Piperidines -- 1.10.1 Iodine catalyzed sp3-H amination -- 1.10.2 Synthesis from 2,6-diaminopimelic acid to piperidine-2,6-dicarboxylic acid -- 1.10.3 A photochemical reaction in the synthesis of azasugar derivatives -- 1.10.4 Piperidines from ring-contaction of N-chlorolactams -- 1.10.5 Synthesis of 2-piperidinone catalyzed from a hydrophobic analog of vitamin B12 -- 1.11 Pyrazoles -- 1.11.1 Aromatization of 1,3,5 trisubstituted pyrazolines -- 1.11.2 Photochemical bromination for preparation of mono, bis and fused pyrazole derivatives -- 1.11.3 Pyrazoles from hydrazines and Michael acceptors -- 1.11.4 Synthesis of pyrazole derivatives via formal [4+1] annulation and aromatization -- 1.11.5 Reaction of hydrazones and α-bromoketones -- 1.11.6 One pot synthesis of pyrazoles from alkynes and hydrazines -- 1.11.7 Sunlight-promoted direct irradiation of N-centered anion: the photocatalyst-free synthesis of pyrazoles -- 1.11.8 Efficient photooxidation of aryl (hetaryl)pyrazolines by benzoquinone -- 1.11.9 Synthesis of pyrazoles via photochemical ring opening of pyridazine N-oxides -- 1.12 Pyridines -- 1.12.1 Pyridines from ring closure of acyloximes -- 1.12.2 Synthesis of naphthyl pyridines from heptadynes and nitriles -- 1.12.3 Synthesis of substituted pyridine from aryl ketone and benzylamines -- 1.12.4 Pyridines from trimerization of two alkenes and a nitrile -- 1.13 Pyrimidines -- 1.13.1 Synthesis of benzo-fused pyrimidines- 4-ones from 1,2,4 oxadiazoles -- 1.13.2 Fluoroalkylates pyrimidines from silyl enol ethers, amidines, and fluoroalkylhalides. , 1.13.3 Three component synthesis from active methylene compounds, perfluoroalkyl iodides and guanidines -- 1.13.4 Synthesis of pyrimidones from 4-allyl-tetrazolones -- 1.14 Pyrroles -- 1.14.1 Dehydrogenative aromatization and sulfonylation of pyrrolidines -- 1.14.2 Synthesis of nitrogen heterocycles generated from α-silyl secondary amines under visible light irradiation -- 1.14.3 Synthesis of substituted pyrroles by dimerization of acyl azirines -- 1.14.4 Photochemical isomerizations of N-substituted 2-halopyrroles: syntheses of N-substituted 3-halopyrroles -- 1.14.5 Synthesis of pentacycles incorporating a pyrrole unit -- 1.14.6 Synthesis of 1,3,4 trisubstituted pyrroles by condensation of aryl azides and aldheydes -- 1.15 Pyrrolidines -- 1.15.1 Pyrrolydinones from suitable amides and an iridium catalyst -- 1.15.2 [3 + 2] Cycloaddition between a cyclopropylketone and an imine -- 1.15.3 Synthesis of pyrrolidines from alkanes and nitrogen derivatives -- 1.15.4 Aroylchlorination of 1,6 dienes to obtain 2-pyrrolidinones -- 1.15.5 Synthesis of pyrrolidinones fused with a cyclobutane ring -- 1.16 Thiophenes and benzothiophenes -- 1.16.1 Cyclization of 2-alkynylanilines with disulfide to afford benzothiophenes -- 1.16.2 Cyclization of diethynil sulfide to thiophene -- References -- 2 Photoisomerization of heterocyclic compounds -- 2.1 Photoisomerization of pentaatomic heterocycles -- 2.1.1 Isomerization of furan derivatives -- 2.1.1.1 Furan -- 2.1.1.2 Methylfurans -- 2.1.1.3 Alkylfurans -- 2.1.1.4 Trimethylsilyl-substituted furans -- 2.1.1.5 Furans bearing electron-donating or electron-withdrawing groups -- 2.1.2 Isomerization of pyrrole -- 2.1.3 Isomerization of thiophene -- 2.1.3.1 Alkylthiophenes -- 2.1.3.2 Arylthiophenes -- 2.1.3.3 Cyanothiophenes -- 2.1.3.4 Other thiophenes -- 2.1.4 Isomerization of isoxazole. , 2.1.4.1 Isoxazoles bearing electron-donating groups -- 2.1.4.2 Isoxazoles bearing electron-withdrawing groups -- 2.1.4.3 Benzisoxazoles -- 2.1.4.4 Isoxazolidones -- 2.1.5 Isomerization of oxazole -- 2.1.6 Isomerization of pyrazole -- 2.1.7 Isomerization of imidazole -- 2.1.8 Isomerization of thiazoles -- 2.1.8.1 Aryl-substituted thiazoles -- 2.1.8.2 Bithiazoles -- 2.1.8.3 Trithiazoles -- 2.1.8.4 Benzothiazole -- 2.1.9 Isomerization of isothiazoles -- 2.1.9.1 Benzoisothiazole -- 2.1.10 Isomerization of oxadiazoles -- 2.1.10.1 1,2,4-Oxadiazoles -- 2.1.10.2 1,2,5-Oxadiazoles -- 2.1.11 Other pentaatomic heterocycles -- 2.2 Photoisomerization of hexatomic heterocycles -- 2.2.1 Isomerization of pyridines -- 2.2.1.1 Pyridines -- 2.2.1.2 Dihydropyridine -- 2.2.1.3 Pyridinium salts -- 2.2.1.4 Pyridinium ylides -- 2.2.1.5 Pyridinium oxide -- 2.2.1.6 Quinolines and isoquinolines -- 2.2.2 Isomerization of diazines -- 2.2.2.1 Pyrazine -- 2.2.2.2 Pyridazine -- 2.2.2.3 Pyrimidine -- 2.2.2.4 Other compounds -- References -- 3 Photochemical behavior of diheteroarylethenes and photochromism -- 3.1 Photochemistry of olefins: An overview -- 3.2 Photoinduced pericyclic reactions: Stilbene and its diheteroarylethenes derivatives -- 3.2.1 Some applications of the Mallory reaction -- 3.3 The [2+2] photocycloaddition reactions on heteroarylethenes -- 3.4 Photochromism of diheteroarylethenes -- 3.4.1 A brief historical overview and basic reaction mechanism -- 3.4.2 Photochromism: Tuning with ethene bridges -- 3.4.3 Photochromism: Tuning with funtionalised heteroaryl groups -- 3.4.4 Photocyclization reactions and solvent effect -- 3.4.5 Photochromism in chiral diheteroarylethenes -- 3.4.6 Ring closure processes induced by visible radiation and all-visible photochromism -- 3.5 Applications of photochromic molecules of diheteroarylethenes: Switches and optical memories. , 3.5.1 Switches.

Additional Edition: Print version: D'Auria, Maurizio Photochemistry of Heterocycles San Diego : Elsevier,c2022 ISBN 9780128237458

Language: English

UID:

Format: 1 online resource (352 pages)

ISBN: 0-12-823746-5

Content: Photochemistry of Heterocycles is a comprehensive review of the topic, including photooxidation, photoreduction and photoaddition reactions as well as industrial aspects of heterocyclic photochemistry. Many materials used for the manufacturing of OLEDs and other electrooptical switches contain heterocycles, and the use of small molecules or polymers containing heterocyclic substances are being studied as new photovoltaic materials. This reference is ideal for synthetic organic chemists, specifically researchers working in organic photochemistry, as well as medicinal chemists and material scientists. Heterocyclic compounds are widely used in the modern world, and most of the drugs currently in use have heterocyclic nuclei among their constituents. These compounds are subject to a photochemical degradation processes which must be known and prevented.

Note: Front Cover -- Photochemistry of Heterocycles -- Copyright Page -- Contents -- Preface -- 1 Photochemical synthesis of heterocyclic compounds -- 1.1 Introduction -- 1.2 Azetidines -- 1.2.1 Synthesis by aza Paternò-Buchi reaction -- 1.2.2 Synthesis by intramolecular closure of N-formil-α-oxoamides -- 1.2.3 Synthesis by Norris-Yang rearrangement -- 1.2.4 Reaction between fullerene and formamidines -- 1.2.5 Synthesis by ciclization of amino ketones -- 1.3 Aziridines -- 1.3.1 Synthesis by rearrangement of pyridinium salts -- 1.3.2 Synthesis by insertion of nitrene into double bonds -- 1.3.3 Synthesis from homoallylpyrroles -- 1.3.4 Synthesis by rearrangement of triazolines -- 1.3.5 Synthesis of aziridines by visible-light induced decarboxylative cyclization of N-aryl glycines and diazo compounds -- 1.3.6 Photoinduced aziridination of alkenes with N-sulfonyliminoiodinane -- 1.3.7 Photochemical aziridination of fullerenes -- 1.3.8 Synthesis from sugar derivatives and azides -- 1.3.9 Synthesis from azides by photocatalysis -- 1.3.10 Synthesis from azidoformates -- 1.4 Diazepines and benzodiazepines -- 1.4.1 Synthesis from 4-pyridyl azides -- 1.5 Furans -- 1.5.1 Furans from α-bromo-β-dicarbonyl compounds and alkynes -- 1.5.2 Benzofurans from 2-chlorophenols and alkynes -- 1.5.3 Dihydro and tetrahydrofurans from cyclopropane derivatives -- 1.5.4 Dihydrofuran from photodimerization of β-carbonyl ketones -- 1.5.5 Tetrasubstituted furans from silylenolethers and α-bromo diketones -- 1.5.6 Synthesis of 5H-furanones from substituted cyclobutenones -- 1.5.7 Photochemical catalytical synthesis of dihydrofurans from vinyl and aryl cyclopropanes -- 1.5.8 Tetrahydrofurans from cyclobutanones and nitrile compounds -- 1.5.9 Reaction of propargyl derivatives with alkenes -- 1.5.10 Tetrahydrofurans from α,β-unsaturated ketones. , 1.5.11 γ-Lactones from allylic alcohols and α,β-unsaturated keto ester -- 1.5.12 Synthesis from cinnamic acid and ketones -- 1.5.13 Synthesis from α-chloro alkyl ketones and styrenes -- 1.5.14 Synthesis by isomerization of alkenes -- 1.6 Imidazoles and derivatives -- 1.6.1 Synthesis of an imidazole intermediated by HCN -- 1.6.2 Synthesis of dihydroimidazoles from pyridinium salts and an alkene -- 1.6.3 Synthesis of an imidazolinone by cyclization of a linear compound -- 1.6.4 Synthesis of purines by irradiation of urea/acetylene -- 1.6.5 One pot synthesis from aldehydes, α-aminonitriles and isoxazoles -- 1.6.6 Reaction of N-(1-methylpyrimidin-2-one)pyridinium chloride. Contraction to an imidazolidinone -- 1.7 Synthesis of oxadiazoles -- 1.7.1 1,2,4 Oxadiazoles from 2H-azirines and nitrosoarenes -- 1.7.2 Photooxidation of N-acylhydrazones to 1,3,4-oxadiazoles -- 1.8 Synthesis of oxazoles and related systems -- 1.8.1 Synthesis of oxazoles by conversion of 1-acyl triazoles -- 1.8.2 Synthesis from α-bromoketones and benzylamines -- 1.8.3 Three components condensation of silylenolethers, fluoroalkyl halides and chiral aminoalcohols to obtain oxazolidines -- 1.8.4 Oxazolidinones from propargylic amines and CO2 -- 1.8.5 Conversion of benzoil formamides to oxazolidin 4-ones -- 1.8.6 Synthesis of phosphonium substituted oxazoles from phosphonium-iodonium ylides -- 1.8.7 Synthesis from azirines and aldehydes -- 1.9 Oxetanes: the Paternò Büchi reaction -- 1.9.1 Exo-oxetanes from carbonyl compounds with vinylene carbonates -- 1.9.2 Photocycloaddition of N-acyl enamines to aldehydes -- 1.9.3 Oxetanes from carbonyl compounds and 2,5 dimethyl-4-isobutyl-oxazoles -- 1.9.4 Reaction of 2,3-dihydrofuran -- 1.9.5 Reaction of a silyl derivative of cinnamyl alcohol -- 1.9.6 Reaction of geraniol derivatives -- 1.9.7 Reaction with isoxazole derivatives. , 1.9.8 Synthesis of an elusive oxetane by photoaddition of benzophenone to thiophene in the presence of a Lewis acid -- 1.9.9 Reaction of 2-furylmethanol derivatives -- 1.9.10 Reaction of silyl enol ethers -- 1.10 Piperidines -- 1.10.1 Iodine catalyzed sp3-H amination -- 1.10.2 Synthesis from 2,6-diaminopimelic acid to piperidine-2,6-dicarboxylic acid -- 1.10.3 A photochemical reaction in the synthesis of azasugar derivatives -- 1.10.4 Piperidines from ring-contaction of N-chlorolactams -- 1.10.5 Synthesis of 2-piperidinone catalyzed from a hydrophobic analog of vitamin B12 -- 1.11 Pyrazoles -- 1.11.1 Aromatization of 1,3,5 trisubstituted pyrazolines -- 1.11.2 Photochemical bromination for preparation of mono, bis and fused pyrazole derivatives -- 1.11.3 Pyrazoles from hydrazines and Michael acceptors -- 1.11.4 Synthesis of pyrazole derivatives via formal [4+1] annulation and aromatization -- 1.11.5 Reaction of hydrazones and α-bromoketones -- 1.11.6 One pot synthesis of pyrazoles from alkynes and hydrazines -- 1.11.7 Sunlight-promoted direct irradiation of N-centered anion: the photocatalyst-free synthesis of pyrazoles -- 1.11.8 Efficient photooxidation of aryl (hetaryl)pyrazolines by benzoquinone -- 1.11.9 Synthesis of pyrazoles via photochemical ring opening of pyridazine N-oxides -- 1.12 Pyridines -- 1.12.1 Pyridines from ring closure of acyloximes -- 1.12.2 Synthesis of naphthyl pyridines from heptadynes and nitriles -- 1.12.3 Synthesis of substituted pyridine from aryl ketone and benzylamines -- 1.12.4 Pyridines from trimerization of two alkenes and a nitrile -- 1.13 Pyrimidines -- 1.13.1 Synthesis of benzo-fused pyrimidines- 4-ones from 1,2,4 oxadiazoles -- 1.13.2 Fluoroalkylates pyrimidines from silyl enol ethers, amidines, and fluoroalkylhalides. , 1.13.3 Three component synthesis from active methylene compounds, perfluoroalkyl iodides and guanidines -- 1.13.4 Synthesis of pyrimidones from 4-allyl-tetrazolones -- 1.14 Pyrroles -- 1.14.1 Dehydrogenative aromatization and sulfonylation of pyrrolidines -- 1.14.2 Synthesis of nitrogen heterocycles generated from α-silyl secondary amines under visible light irradiation -- 1.14.3 Synthesis of substituted pyrroles by dimerization of acyl azirines -- 1.14.4 Photochemical isomerizations of N-substituted 2-halopyrroles: syntheses of N-substituted 3-halopyrroles -- 1.14.5 Synthesis of pentacycles incorporating a pyrrole unit -- 1.14.6 Synthesis of 1,3,4 trisubstituted pyrroles by condensation of aryl azides and aldheydes -- 1.15 Pyrrolidines -- 1.15.1 Pyrrolydinones from suitable amides and an iridium catalyst -- 1.15.2 [3 + 2] Cycloaddition between a cyclopropylketone and an imine -- 1.15.3 Synthesis of pyrrolidines from alkanes and nitrogen derivatives -- 1.15.4 Aroylchlorination of 1,6 dienes to obtain 2-pyrrolidinones -- 1.15.5 Synthesis of pyrrolidinones fused with a cyclobutane ring -- 1.16 Thiophenes and benzothiophenes -- 1.16.1 Cyclization of 2-alkynylanilines with disulfide to afford benzothiophenes -- 1.16.2 Cyclization of diethynil sulfide to thiophene -- References -- 2 Photoisomerization of heterocyclic compounds -- 2.1 Photoisomerization of pentaatomic heterocycles -- 2.1.1 Isomerization of furan derivatives -- 2.1.1.1 Furan -- 2.1.1.2 Methylfurans -- 2.1.1.3 Alkylfurans -- 2.1.1.4 Trimethylsilyl-substituted furans -- 2.1.1.5 Furans bearing electron-donating or electron-withdrawing groups -- 2.1.2 Isomerization of pyrrole -- 2.1.3 Isomerization of thiophene -- 2.1.3.1 Alkylthiophenes -- 2.1.3.2 Arylthiophenes -- 2.1.3.3 Cyanothiophenes -- 2.1.3.4 Other thiophenes -- 2.1.4 Isomerization of isoxazole. , 2.1.4.1 Isoxazoles bearing electron-donating groups -- 2.1.4.2 Isoxazoles bearing electron-withdrawing groups -- 2.1.4.3 Benzisoxazoles -- 2.1.4.4 Isoxazolidones -- 2.1.5 Isomerization of oxazole -- 2.1.6 Isomerization of pyrazole -- 2.1.7 Isomerization of imidazole -- 2.1.8 Isomerization of thiazoles -- 2.1.8.1 Aryl-substituted thiazoles -- 2.1.8.2 Bithiazoles -- 2.1.8.3 Trithiazoles -- 2.1.8.4 Benzothiazole -- 2.1.9 Isomerization of isothiazoles -- 2.1.9.1 Benzoisothiazole -- 2.1.10 Isomerization of oxadiazoles -- 2.1.10.1 1,2,4-Oxadiazoles -- 2.1.10.2 1,2,5-Oxadiazoles -- 2.1.11 Other pentaatomic heterocycles -- 2.2 Photoisomerization of hexatomic heterocycles -- 2.2.1 Isomerization of pyridines -- 2.2.1.1 Pyridines -- 2.2.1.2 Dihydropyridine -- 2.2.1.3 Pyridinium salts -- 2.2.1.4 Pyridinium ylides -- 2.2.1.5 Pyridinium oxide -- 2.2.1.6 Quinolines and isoquinolines -- 2.2.2 Isomerization of diazines -- 2.2.2.1 Pyrazine -- 2.2.2.2 Pyridazine -- 2.2.2.3 Pyrimidine -- 2.2.2.4 Other compounds -- References -- 3 Photochemical behavior of diheteroarylethenes and photochromism -- 3.1 Photochemistry of olefins: An overview -- 3.2 Photoinduced pericyclic reactions: Stilbene and its diheteroarylethenes derivatives -- 3.2.1 Some applications of the Mallory reaction -- 3.3 The [2+2] photocycloaddition reactions on heteroarylethenes -- 3.4 Photochromism of diheteroarylethenes -- 3.4.1 A brief historical overview and basic reaction mechanism -- 3.4.2 Photochromism: Tuning with ethene bridges -- 3.4.3 Photochromism: Tuning with funtionalised heteroaryl groups -- 3.4.4 Photocyclization reactions and solvent effect -- 3.4.5 Photochromism in chiral diheteroarylethenes -- 3.4.6 Ring closure processes induced by visible radiation and all-visible photochromism -- 3.5 Applications of photochromic molecules of diheteroarylethenes: Switches and optical memories. , 3.5.1 Switches.

Additional Edition: Print version: D'Auria, Maurizio Photochemistry of Heterocycles San Diego : Elsevier,c2022 ISBN 9780128237458

Language: English

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Format: ix, 340 Seiten : , Illustrationen, Diagramme.

ISBN: 978-0-12-823745-8

Additional Edition: Erscheint auch als Online-Ausgabe ISBN 978-0-12-823746-5

Language: English

Subjects: Chemistry/Pharmacy