Synthesis 2018; 50(04): 872-880
DOI: 10.1055/s-0036-1590947
paper
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Malononitrile-Substituted Diarylmethines via 1,6-Addition of Masked Acyl Cyanides to para-Quinone Methides

Kun Zhao
a   Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany   Email: enders@rwth-aachen.de
,
Ying Zhi
a   Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany   Email: enders@rwth-aachen.de
,
Ai Wang
b   Institute of Inorganic Chemistry, RWTH Aachen University, Landoltweg 1, 52074, Aachen, Germany
,
Dieter Enders*
a   Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany   Email: enders@rwth-aachen.de
› Author Affiliations
Further Information

Publication History

Received: 06 October 2017

Accepted: 09 October 2017

Publication Date:
23 November 2017 (online)


Abstract

An efficient method for the synthesis of malononitrile-substituted­ diarylmethines through 1,6-conjugate addition of para-quinone­ methides with masked acyl cyanide (MAC) reagents has been developed. Under mild conditions, the scalable reaction occurs in good to excellent yields providing a straightforward access to a series of malononitrile-substituted diarylmethines. The synthetic utility of this protocol has been demonstrated in the synthesis of bioactive compounds.

Supporting Information