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

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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21

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) Å^³, 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.