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1. One-pot synthesis of tetrahydro-pyrrolobenzodiazepines and tetrahydro-pyrrolobenzodiazepinones through sequential 1,3-dipolar cycloaddition/N-alkylation (N-acylation)/Staudinger/aza-Wittig reactions

Author

Xiaoming Ma, John Mark Awad, Weiqi Qiu, Wei Zhang, Guoshu Xie, and Xiaofeng Zhang

Subjects
010405 organic chemistry, Chemistry, One-pot synthesis, Alkylation, 010402 general chemistry, 01 natural sciences, Pollution, Cycloaddition, 0104 chemical sciences, N acylation, Wittig reaction, 1,3-Dipolar cycloaddition, Environmental Chemistry, Organic chemistry, Green chemistry metrics
Abstract

A new synthetic method for diastereoselective synthesis of tetrahydro-pyrrolo[1,2-d][1,4]benzodiazepines and tetrahydro-pyrrolo[1,2-d][1,4]diazepinones is developed which involves 1,3-dipolar cycloaddition, N-alkylation or N-acylation and Staudinger/aza-Wittig reactions. This one-pot and three-step synthesis of four components gave two different heterocyclic scaffolds. Green chemistry metrics analysis of the reaction process provided favorable results.

Published
2019

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