In:
Synthesis, Georg Thieme Verlag KG, Vol. 54, No. 17 ( 2022-09), p. 3809-3816
Abstract:
The synthesis of alicyclic 2-methylenethiazolo[2,3-b]quinazolinones is performed via base-promoted cascade reactions, starting from either alicyclic β-amino propargylamides using carbon disulfide, or from alicyclic ethyl 2-isothiocyanatocarboxylates by addition of propargylamine. In both cases the cascade reaction proceeds by way of a favoured 5-exo-dig process during the second ring closure, as confirmed by full NMR spectroscopic assignments. Moreover, a high-yielding retro-Diels–Alder (RDA) reaction is performed on the norbornene derivatives leading to 2-methylene-2H-thiazolo[3,2-a] pyrimidin-5(3H)-ones. The obtained compounds exert modest antiproliferative activities against a panel of human gynaecological cancer cell lines.
Type of Medium:
Online Resource
ISSN:
0039-7881
,
1437-210X
DOI:
10.1055/s-0040-1720028
Language:
English
Publisher:
Georg Thieme Verlag KG
Publication Date:
2022
detail.hit.zdb_id:
204080-3
detail.hit.zdb_id:
2033062-5
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