Synthesis 2019; 51(04): 960-970
DOI: 10.1055/s-0037-1610662
paper
© Georg Thieme Verlag Stuttgart · New York

A Route to Highly Functionalized Stereospecific trans-Aminated Aurones from 3-Bromoflavones with Aniline and N-Phenylurea via a Domino Aza-Michael Ring Opening and Cyclization Reactions

Iram Parveen
,
Naseem Ahmed*
Department of Chemistry, Indian Institute of Technology Roorkee, Roorkee 247 667, India   Email: nasemfcy@iitr.ac.in
› Author Affiliations
I.P. is thankful to UGC (Grant No: 6405-13-044), New Delhi for a fellowship.
Further Information

Publication History

Received: 18 August 2018

Accepted after revision: 11 September 2018

Publication Date:
10 October 2018 (eFirst)

Abstract

A facile cascade reaction is reported via aza-Michael addition, ring opening, and cyclization between 3-bromoflavone and aniline derivatives or N-phenylurea in the presence of KOt-Bu and CuI in DMF under mild reaction conditions. Products were obtained as stereospecific trans-aminated aurones in good to excellent yields (61–83%). Our protocol is operationally successful with ease, avoids the requirement of additives and ligands, and offers broad substrate scope.

Supporting Information

 
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