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Reactions of alkyl (z)-2-[(E)-2-ethoxycarbonyl-2-(2-pyridinyl)-ethenyl]amino-3-dimethylaminopropenoates with C- and N-nucleophiles. the synthesis of fused pyranones, pyridinones and pyrimidinones

✍ Scribed by Lucija Jukić; Jurij Svete; Branko Stanovnik

Publisher
Journal of Heterocyclic Chemistry
Year
2001
Tongue
English
Weight
84 KB
Volume
38
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

Alkyl 2‐[2‐ethoxycarbonyl‐2‐(2‐pyridinyl)ethenyl]amino‐3‐dimethylaminopropenoates 3 and 4 were transformed with C‐and N‐nucleophiles into β‐heteroaryl‐α,β‐didehydro‐α‐amino acid derivatives 13‐16, substituted 3‐amino‐4__H__‐quinolizin‐4‐one 17, 2__H__,5__H__‐benzo[b]pyran‐2,5‐dione 18 and 19, 2__H__,5__H__‐pyrano[4,3‐b]pyran‐2,5‐dione 20, 2__H__,5__H__‐pyrano[3,2‐c]benzo[b]pyran‐2,5‐dione 21, 2__H__‐1‐benzopyran‐2‐one 22 and 24, pyrido[l,2‐a]pyrimidin‐4‐one 31–34 and 39 derivatives, and N‐heteroaryl‐1__H__‐imidazole‐4‐carboxylates 37 and 38.

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## Abstract Alkyl (Z)‐2‐[(__E__)‐2‐ethoxycarbonyl‐2‐(2‐pyridinyl)ethenyl]amino‐3‐dimethylaminopropenoates **7** and **8** were prepared from ethyl 2‐pyridinylacetate (1) in two steps. Substitution of the dimethylamino group with alkyl‐, aryl‐, or heteroarylamines afforded the corresponding β‐alkyl‐