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通过钯/二异丙基联苯膦催化的去芳构化羰基化反应合成吡啶并[2,1 - b]喹唑啉 - 11 - 酮和二吡啶并[1,2 - a:2',3'- d]嘧啶 - 5 - 酮

Synthesis of pyrido[2,1-b]quinazolin-11-ones and dipyrido[1,2-a:2',3'-d]pyrimidin-5-ones by Pd/DIBPP-catalyzed dearomatizing carbonylation.

作者信息

Xu Tongyu, Alper Howard

机构信息

Centre for Catalysis Research and Innovation, Department of Chemistry, University of Ottawa, 10 Marie Curie, Ottawa, Ontario Canada, K1N 6N5.

出版信息

Org Lett. 2015 Mar 20;17(6):1569-72. doi: 10.1021/acs.orglett.5b00452. Epub 2015 Mar 10.

Abstract

N-Fused heterocycles can be easily synthesized by palladium-catalyzed dearomatizing carbonylation using 1,3-bis(diisobutylphosphino)propane (DIBPP) as the ligand. Pyrido[2,1-b]quinazolin-11-ones were obtained from N-(2-bromophenyl)pyridine-2-amines in up to quantitative yield and dipyrido[1,2-a:2',3'-d]pyrimidin-5-ones from 3-bromo-N-(pyridine-2-yl)pyridine-2-amines in up to 84% yield. The cyclocarbonylation can be also realized without isolation of compound 1 and additional palladium catalyst.

摘要

使用1,3-双(二异丁基膦基)丙烷(DIBPP)作为配体,通过钯催化的去芳构化羰基化反应可以轻松合成N-稠合杂环。从N-(2-溴苯基)吡啶-2-胺中获得吡啶并[2,1-b]喹唑啉-11-酮,产率高达定量,从3-溴-N-(吡啶-2-基)吡啶-2-胺中获得二吡啶并[1,2-a:2',3'-d]嘧啶-5-酮,产率高达84%。环羰基化反应也可以在不分离化合物1和额外钯催化剂的情况下实现。

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