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Alkyl (E,Z)-2-(2-benzoyl-2-ethoxycarbonyl-1-ethenyl)amino-3-dimethylaminopropenoates in the synthesis of fused pyrimidinones. A facile route to 3-aminoazino-4H-pyrimidin-4-ones
✍ Scribed by Sonja Strah; Amalija Golobič; Ljubo Golič; Branko Stanovnik
- Publisher
- Journal of Heterocyclic Chemistry
- Year
- 1997
- Tongue
- English
- Weight
- 580 KB
- Volume
- 34
- Category
- Article
- ISSN
- 0022-152X
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✦ Synopsis
Abstract
Alkyl (E,Z)‐2‐(2‐benzoyl‐2‐ethoxycarbonyl‐1‐ethenyl)amino‐3‐dimethylaminopropenoates 1a,b react with het‐eroarylamines 2 to give alkyl 2‐(2‐benzoyl‐2‐ethoxycarbonyl‐1‐ethenyl)amino‐3‐heteroarylaminopropenoates 3‐13. These were cyclized into fused 3‐(2‐benzoyl‐2‐ethoxycarbonyl‐1‐ethenyl)amino‐4__H__‐azolo‐ (or azino)‐pyrim‐idin‐4‐ones 14‐18. 2‐Benzoyl‐2‐ethoxycarbonyl‐1‐ethenyl group can be easily removed from 3‐(2‐benzoyl‐2‐ethoxycarbonyl‐1‐emenyl)amino‐8‐memyl‐4__H__‐pyrido[1,2‐a]pyrimidin‐4‐one (14) to give 3‐amino‐8‐methyl‐4__H__‐pyrido[1,2‐a]pyrimidin‐4‐one (19). The structure of 1a was confirmed by X‐ray analysis.
📜 SIMILAR VOLUMES
## 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__‐benz