Domino synthesis of pyrimido and imidazoquinazolinones,Journal of Heterocyclic Chemistry

当前位置： X-MOL 学术 › J. Heterocycl. Chem. › 论文详情

Our official English website, www.x-mol.net, welcomes your feedback! (Note: you will need to create a separate account there.)

Domino synthesis of pyrimido and imidazoquinazolinones
Journal of Heterocyclic Chemistry ( IF 2.0 ) Pub Date : 2019-12-29 , DOI: 10.1002/jhet.3864
Walid Fathalla ₁ , Eman Y. Nofal ₁ , Mohamed Abd El‐Moneim ₂

Affiliation

A simple method for the synthesis of N‐alkyl‐2‐arylquinazolin‐4‐amines, methyl 4‐((2‐arylquinazolin‐4‐yl)amino) butanoates, 6‐aryl‐2,3‐dihydro‐4H‐pyrimido[1,2‐c]quinazolin‐4‐ones, and 5‐arylimidazo[1,2‐c]quinazolin‐3(2H)‐ones has been described. It involves a simple reaction of N‐(2‐cyanophenyl)‐substitutedbenzimidoyl chlorides with alkylamine, γ‐aminobutyric acid, β‐alanine, l‐alanine, and glycine methyl esters hydrochloride in acetonitrile to afford the desired compounds after a series of instantaneous reactions that include Dimroth rearrangement. The reaction involves reflux for 12 hours, simple addition of reagents to an in situ generated benzimidoyl chloride, and simple workup, to form 21 examples of pure compounds in high yields. The active intermediate N‐(2‐cyanophenyl)‐substitutedbenzimidoyl chlorides were formed by the reaction of N‐(2‐cyanophenyl)‐substitutedbenzamides with thionyl chloride in a one‐pot strategy. The alternative method described for this preparation deals with an exhausting multistep reactions starting from anthranilic acid.

中文翻译：

嘧啶和咪唑并喹唑啉酮的多米诺合成

一种简单的合成N-烷基-2-芳基喹唑啉-4-胺，4-（（（2-芳基喹唑啉-4-基）氨基）丁酸甲酯，6-芳基-2-3,3-二氢-4 H-嘧啶基的方法已经描述了[1,2 - c ]喹唑啉-4-酮和5-芳基咪唑[1,2 - c ]喹唑啉-3（2 H）-酮。它涉及N-（2-氰基苯基）-取代的苯甲酰氯与烷基胺，γ-氨基丁酸，β-丙氨酸，l的简单反应丙氨酸和甘氨酸甲酯盐酸盐在乙腈中，经过一系列包括Dimroth重排的瞬时反应后，可提供所需的化合物。该反应包括回流12小时，将试剂简单地添加到原位生成的苯二甲酰氯中，并且简单地后处理，以高收率形成21个纯化合物的实例。活性中间体ñ - （2-氰基苯基）-substitutedbenzimidoyl氯化物通过反应形成的Ñ - （2-氰基苯基）-substitutedbenzamides与在亚硫酰氯一锅策略。为该制备方法描述的替代方法涉及从邻氨基苯甲酸开始的详尽的多步反应。

更新日期：2019-12-30

点击分享查看原文

点击收藏

阅读更多本刊最新论文本刊介绍/投稿指南11