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Biginelli Synthesis of Regioisomeric 5,6-Dihydro-4 H -benzo[4,5]imidazo[1,2- a ]pyranopyrimidin-4-ones
Russian Journal of Organic Chemistry ( IF 0.8 ) Pub Date : 2020-11-24 , DOI: 10.1134/s1070428020100139
I. V. Kanevskaya , A. S. Bondartsova , O. V. Fedotova

Abstract

A modified version of the three-component Biginelli reaction of 4-hydroxy-6-methyl-2H-pyran-2-one with aromatic aldehydes and 1H-benzimidazol-2-amine has been studied under thermal and microwave activation. Depending on the substituent in the initial aldehyde, angularly fused 5,6-dihydro-4H-benzo[4,5]imidazo[1,2-a]pyranopyrimidin-4-ones or 2-amino-1H-benzimidazol-3-ium arylbis(4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)methanides have been obtained. A plausible mechanism of their formation has been proposed.



中文翻译:

Biginelli合成区域异构体5​​,6-二氢-4 H-苯并[4,5]咪唑并[1,2- a]吡喃并嘧啶-4-酮

摘要

在热和微波活化下,研究了4-羟基-6-甲基-2 H-吡喃-2-酮与芳族醛和1 H-苯并咪唑-2-胺的三组分Biginelli反应的改进形式。根据起始醛中的取代基,有角度地稠合5,6-二氢-4 H-苯并[4,5]咪唑并[1,2- a ]吡喃并嘧啶-4-酮或2-氨基-1 H-苯并咪唑-3已经获得了芳基双(4-羟基-6-甲基-2-氧代-2- H-吡喃-3-基)甲铵盐。已经提出了它们形成的合理机制。

更新日期:2020-11-25
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