One-step synthesis of aminopyrimidines from 5-Oxo-4H-benzopyrans
✍ Scribed by Esperanza Salfrán; Carlos Seoaneb; Margarita Suárez; Yamila Verdecia; Amaury Alvarez; Estael Ochoa; Roberto Martínez-Alvarez; Nazario Martín
- Book ID
- 102341991
- Publisher
- Journal of Heterocyclic Chemistry
- Year
- 2004
- Tongue
- English
- Weight
- 227 KB
- Volume
- 41
- Category
- Article
- ISSN
- 0022-152X
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✦ Synopsis
Abstract
Novel 4‐amino‐6‐aryl‐2‐phenylpyrimidine‐5‐carbonitriles have been prepared in one step procedure from the readily available 4‐aryl‐2‐amino‐3‐cyano‐5,6,7,8‐tetrahydro‐7,7‐dimethyl‐5‐oxo‐4__H__‐benzopyrans. The mass spectroscopy study under EI conditions shows molecular peaks with high intensity corresponding to the loss of benzonitrile from the C2 position of the pyrimidine ring. Semiempirical (AMI and PM3) and ab initio HF/6–31G* calculations reveal a favored distorted geometry where the three rings are not in the same plane.
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## Abstract magnified image The title aldehyde **1** reacts smoothly with the enamine moiety of **2**‐aminochromone **2** to produce hitherto unreported 3‐(2‐hydroxybenzoyl)‐5__H__‐1‐benzopyrano[2,3‐__b__]pyridin‐5‐one (azaxanthone) **5**. This reaction has been extended for the synthesis of bisaz