In:
ChemistrySelect, Wiley, Vol. 7, No. 30 ( 2022-08-12)
Kurzfassung:
Unsubstituted and 1‐methyl‐substituted 1,3,4,8b‐tetrahydrodiazirino[3,1‐ a ]isoquinolines (diaziridines 1 and 2 ) demonstrate different reactivities toward aryl isocyanates and aryl isothiocyanates. Diaziridine 1 reacts with aryl isocyanates as a nucleophile to afford novel 1,5,6,10b‐tetrahydro[1,2,4]triazolo[5,1‐ a ]isoquinolines. The addition of a Lewis or Brønsted acid switches the reaction pathway, producing seven‐membered 2,3‐benzodiazepines. In reactions of diaziridine 1 with aryl isothiocyanates, unusual zwitterionic compounds – 2‐thioxo‐5,6‐dihydro‐2 H ‐[1,2,4]triazolo[5,1‐ a ]isoquinolin‐1‐ium‐3‐ides – and products of the addition of two molecules of diaziridine 1 to one molecule of aryl isothiocyanate are obtained. However, in reactions with aryl iso(thio)cyanates under heating or acid catalysis, diaziridine 2 is first converted into an azomethine imine, the 1,3‐dipolar cycloaddition of which to the dipolarophile produces substituted triazolo[5,1‐ a ]isoquinolin‐2(3 H )‐(thi)ones. Proposed is a new method for azomethine imine generation from diaziridine 2 enabled by Brønsted acid catalysis. Antitumour activity of select compounds obtained was assayed to help guide future drug discovery efforts.
Materialart:
Online-Ressource
ISSN:
2365-6549
,
2365-6549
DOI:
10.1002/slct.202202627
Sprache:
Englisch
Verlag:
Wiley
Publikationsdatum:
2022
ZDB Id:
2844262-3