Journal of Organic Chemistry p. 4822 - 4827 (1990)
Update date:2022-08-02
Topics:
Sommer, Michael Bech
Begtrup, Mikael
Boegesoe, Klaus Peter
(2-Cyanoaryl)arylacetonitriles, obtained from o-halogen-substituted cyanoaromatics and arylacetonitriles may be alkylated with methyl chloroacetate.Subsequent abstraction of the proton adjacent to the ester group followed by attack of the anion at the aromatic cyano group gives rise to annulated 1-aminocyclopentenes by a Dieckmann-type reaction.The homologous esters similarly produce annulated 1-aminocyclohexenes.The generality of this annulation method is demonstrated by preparation of derivatives of 1-amino-1H-indene, 4-amino-6H-cyclopentathiophene, 5-amino-7H-pyrindine, 1-amino-3,4-dihydronaphthalene, and 5-amino-2,9-dihydro-1H-cyclopent
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