Synthesis of unsymmetrical 3, 4-diaryl-3-pyrrolin-2-ones utilizing pyrrole weinreb amides

JG Greger, SJP Yoon-Miller, NR Bechtold…

Index: Greger, Jessica G.; Yoon-Miller, Sarah J. P.; Bechtold, Nathan R.; Flewelling, Scott A.; MacDonald, Jacob P.; Downey, Catherine R.; Cohen, Eric A.; Pelkey, Erin T. Journal of Organic Chemistry, 2011 , vol. 76, # 20 p. 8203 - 8214

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Citation Number: 32

Abstract

A regiocontrolled synthesis of unsymmetrical 3, 4-diaryl-3-pyrrolin-2-ones has been achieved in three steps from 1, 2-diaryl-1-nitroethenes with pyrrole-2-carboxamides (pyrrole Weinreb amides) serving as the key linchpin intermediates. Two different methods for the preparation of the requisite nitroalkenes were investigated:(1) modified Henry reaction between arylnitromethanes and arylimines; and (2) Suzuki–Miyaura cross-coupling ...