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Synthesis 2012(7): 1069-1073  
DOI: 10.1055/s-0031-1289718
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of 2-(1-Aryl-2-nitroethyl)-3-arylaminoacrylates via Domino Reaction of Arylamines, Methyl Propiolate, and Nitrostyrenes

Jing Sun, Yan Sun, Hong Gao, Chao-Guo Yan*
College of Chemistry & Chemical Engineering, Yangzhou University, Yangzhou 225002, P. R. of China
Fax: +86(514)87975531; e-Mail: cgyan@yzu.edu.cn;
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Publication History

Received 31 December 2011
Publication Date:
17 February 2012 (online)

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Abstract

An efficient synthetic protocol for 2-(1-aryl-2-nitroethyl)-3-arylaminoacrylates was successfully developed by the one-pot domino reaction of arylamines, methyl propiolate, and nitrostyrenes. The reaction involves the formation of β-enamino ester and its sequential Michael addition to nitrostyrene.

Key words

domino reaction - β-enamino ester - electron-deficient alkyne - nitrostyrene - acrylate

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Single crystal data for compounds 1d (CCDC 827899) and 1g (CCDC 827896) have been deposited at the Cambridge Crystallographic Data Center. These data can be obtained free of charge at www.ccdc.cam.ac.uk/conts/retrieving.html [or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44 (1223)336033, E-mail: deposit@ccdc.cam.ac.uk].