Facile Access to 1,5-Benzodiazepines via Amine-Promoted (4+3) Annulations of δ-Acetoxy Allenoates with o-Diaminobenzenes under Mild Conditions-Reference-Cited by-同舟云学术

Facile Access to 1,5-Benzodiazepines via Amine-Promoted (4+3) Annulations of δ-Acetoxy Allenoates with o-Diaminobenzenes under Mild Conditions

Published:2018-03-23 Issue:09 Volume:29 Page:1176-1180
ISSN:0936-5214
Container-title:Synlett
language:en
Short-container-title:Synlett

Author:

Wang Yi-Fan¹,He Cheng-Yu²,Hou Longlei¹,Tian Ping²³^ORCID,Lin Guo-Qiang²³,Tong Xiaofeng¹

Affiliation:

1. Key Laboratory for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology

2. Key Laboratory of Synthetic Chemistry of Natural Substances, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences

3. Innovation Research Institute of Traditional Chinese Medicine (IRI), Shanghai University of Traditional Chinese Medicine

Abstract

An amine-promoted (4+3) annulation of δ-acetoxy allenoate with o-diaminobenzene is reported, providing a facile access to 1,5-benzodiazepine. This method features wide reaction scope, mild conditions, and readily available starting materials. The cascade reaction involves aza-Michael addition of o-diaminobenzene to allenoate, elimination of acetate group, and subsequent 1,6-aza-Michael addition.

Funder

National Natural Science Foundation of China

Publisher

Georg Thieme Verlag KG

Subject

Organic Chemistry

Link

http://www.thieme-connect.de/products/ejournals/pdf/10.1055/s-0037-1609347.pdf

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