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DABCO- and DBU-promoted one-pot reaction of N -sulfonyl ketimines with Morita–Baylis–Hillman carbonates: a sequential approach to (2-hydroxyaryl)nicotinate derivatives
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DABCO- and DBU-promoted one-pot reaction of N -sulfonyl ketimines with Morita–Baylis–Hillman carbonates: a sequential approach to (2-hydroxyaryl)nicotinate derivatives
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DABCO- and DBU-promoted one-pot reaction of N -sulfonyl ketimines with Morita–Baylis–Hillman carbonates: a sequential approach to (2-hydroxyaryl)nicotinate derivatives
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Journal Article
DABCO- and DBU-promoted one-pot reaction of N -sulfonyl ketimines with Morita–Baylis–Hillman carbonates: a sequential approach to (2-hydroxyaryl)nicotinate derivatives
2018
Overview
An intriguing DABCO-catalyzed and DBU-promoted one-pot synthesis of an important class of (2-hydroxyaryl)pyridine derivatives bearing a carboxylate or a nitrile group suitably placed at C3 position of the aza-ring has been achieved in acceptable chemical yields with a broad functional group tolerance. This sequential C–C/C–N bond making process proceeds through a regioselective allylic alkylation/aza-Michael reaction between MBH carbonates derived from an acrylate/acrylonitrile and N -sulfonyl ketimines as C,N-binucleophiles catalyzed by DABCO, followed by elimination of SO 2 under the influence of base and subsequent aromatization in an open atmosphere.
Publisher
Beilstein-Institut zur Föerderung der Chemischen Wissenschaften,Beilstein-Institut
Subject
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