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Synthesis 2010(9): 1526-1530  
DOI: 10.1055/s-0029-1218717
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A Novel Synthesis of 3-Aryl-2,6-dicyano-5-methylanilines via Reaction between Nitrostyrenes and Malononitrile

Mehdi Adib*a, Bagher Mohammadia, Samira Ansaria, Hamid R. Bijanzadehb, Long-Guan Zhuc
a School of Chemistry, University College of Science, University of Tehran, P.O. Box 14155-6455, Tehran, Iran
Fax: +98(21)66495291; e-Mail: madib@khayam.ut.ac.ir;
b Department of Chemistry, Tarbiat Modarres University, P.O. Box 14115-175, Tehran, Iran
c Chemistry Department, Zhejiang University, Hangzhou 310027, P. R. of China
Further Information

Publication History

Received 12 October 2009
Publication Date:
26 March 2010 (online)

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Abstract

A novel and simple synthesis of 3-aryl-2,6-dicyano-5-methylanilines is described. Reactions between nitrostyrenes and excess malononitrile in the presence of sodium carbonate in 80% ethanol proceeded at room temperature to afford the aromatic products in good yields. A mechanism for the formation of the products is proposed.

Key words

2,6-dicyanoanilines - nitrostyrenes - aromatics - regio­selective - cyclizations

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Selected X-ray crystallographic data for compound 2a: C15H11N3, monoclinic, space group = P21/c, a = 3.9096(5) Å, b = 21.267(3) Å, c = 14.7077(19) Å, β = 95.388(2)˚, V = 1217.50(4) ų, T = 295(2) K, Z = 4, D calcd = 1.27 g×cm-³, µ (Mo-Kα) = 0.078 mm-¹, 1579 observed reflections, final R1 = 0.058, wR2 = 0.150 and for all data R1 = 0.085, wR2 = 0.163. Crystallographic data for compound 2a have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC 734566. Copies of these data can be obtained free of charge from the CCDC via www.ccdc.cam.ac.uk/data_request/cif.