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

Author:

Ma Xiaoming1234ORCID,Zhang Xiaofeng5678ORCID,Awad John Mark5678,Xie Guoshu5678,Qiu Weiqi5678,Zhang Wei5678ORCID

Affiliation:

1. School of Pharmaceutical Engineering and Life Science

2. Changzhou University

3. Jiangsu 213164

4. P. R. China

5. Department of Chemistry

6. University of Massachusetts Boston

7. Boston

8. USA

Abstract

A new diastereoselective synthesis of benzodiazepines and diazepinones is developed. This one-pot and three-step synthesis of four components gave two different heterocyclic scaffolds. Green chemistry metrics analysis of the reaction processes provided favorable results.

Publisher

Royal Society of Chemistry (RSC)

Subject

Pollution,Environmental Chemistry

Reference48 articles.

1. Seven-Membered Rings , in Progress in Heterocyclic Chemistry , ed. G. W. Gribble and J. A. Joule , Elsevier , Cambridge , 2018 , vol. 30

2. Comprehensive Heterocyclic Chemistry III , ed. A. R. Katritzky , Elsevier , Oxford , 2008 , vol. 13

3. Bicyclic Diazepines: Diazepines with an Additional Ring , in The Chemistry of Heterocyclic Compounds , ed. R. I. Fryer , Wiley , New York , 2008

4. The benzodiazepine site of the GABA receptor: an old target with new potential?

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