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聚乙二醇400中的环境友好反应:一种使用2-氨基苄胺立体选择性合成多取代3,4-二氢-2(1)-喹唑啉的高效绿色方法

Eco-friendly reactions in PEG-400: a highly efficient and green approach for stereoselective access to multisubstituted 3,4-dihydro-2(1)-quinazolines using 2-aminobenzylamines.

作者信息

Sharma Nutan, Sharma Pankaj, Bhagat Sunita

机构信息

Organic Synthesis Research Laboratory, Department of Chemistry, A. R. S. D. College, University of Delhi New Delhi-110021 India

出版信息

RSC Adv. 2018 Feb 26;8(16):8721-8731. doi: 10.1039/c7ra13487h. eCollection 2018 Feb 23.

Abstract

An efficient and stereoselective synthesis of novel 3,4-dihydro-2(1)-quinazolines has been developed through cyclization reactions of 2-aminobenzylamines with α-oxoketene dithioacetals using PEG-400 as an inexpensive, easy to handle, non-toxic and recyclable reaction medium. The developed protocol is operationally simple and tolerates various substrates having different functionalities. This protocol features several attributes such as excellent yields, no work up, green reaction conditions, and being environmentally benign. The attractive feature of this new strategy is that all the reported final compounds have been isolated as single ()-stereoisomeric forms, which was confirmed by HNMR and X-ray crystallographic studies.

摘要

通过2-氨基苄胺与α-氧代烯酮二硫代缩醛的环化反应,以聚乙二醇-400作为廉价、易于操作、无毒且可回收的反应介质,开发了一种高效且立体选择性合成新型3,4-二氢-2(1)-喹唑啉的方法。所开发的方案操作简单,能耐受具有不同官能团的各种底物。该方案具有几个特点,如产率优异、无需后处理、绿色反应条件且对环境友好。这一新策略的吸引人之处在于,所有报道的最终化合物均以单一的()-立体异构体形式分离得到,这通过核磁共振氢谱和X射线晶体学研究得以证实。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f2ca/9078610/992b88001cda/c7ra13487h-f1.jpg

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