Tetrahedron Letters

New aromatic rearrangement accompanying ring closure of 2-arylpropylidenemalonodinitriles to 1-aminonaphthalene-2-carbonitriles

JJ Sepiol, J Wilamowski

文献索引：Sepiol, Janusz J; Wilamowski, Jaroslaw Tetrahedron Letters, 2001 , vol. 42, # 31 p. 5287 - 5289

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被引用次数: 12

摘要

Cyclization and a rearrangement in concentrated sulfuric acid of 2-(4-substituted-phenyl) propylidenemalonodinitriles (1) into 1-amino-4-methyl-6-substituted-naphthalene-2- carbonitriles (5) appears to involve a series of steps such as ipso electrophilic attack of the protonated nitrile function on the para position of the phenyl group, opening of a spirobenzenium cation or its transformation, and ring reclosure to the naphthalene ...