174534-15-7Relevant articles and documents
Efficient synthesis of 1-amino-2-naphthalenecarboxylic acid derivatives via a sequential Michael addition/enolate-nitrile coupling route and its application to facile preparation of 9-amino analogues of arylnaphthofuranone lignans
Kobayashi,Uneda,Takada,Tanaka,Kitamura,Morikawa,Konishi
, p. 664 - 668 (2007/10/03)
The reaction of 2-(α-lithioalkyl)benzonitriles, generated in situ by treatment of 2-alkylbenzonitriles with LDA in diglyme, with α,β-unsaturated carboxylates and nitriles produced 1-amino-3,4-dihydro-2-naphthalenecarboxylates and carbonitriles in 54-98% yields through Michael addition of the lithio nitriles to α,β-unsaturated carboxylic acid derivatives, followed by zinc iodide-promoted intramolecular enolate-nitrile coupling of the resulting enolate intermediates. The dihydronaphthalenecarboxylic acid derivatives were converted to the corresponding 1-amino-2-naphthalenecarboxylic acid derivatives in 43-99% yields on dehydrogenation with palladium on activated carbon in refluxing p-cymene. Subsequently, we showed that, by using a similar reaction sequence, 9-amino analogues of arylnaphthofuranone lignan derivatives {9-amino-4-arylnaphtho[2,3-c]furan-1(3H)ones} could also be prepared from 2-(arylmethyl)benzonitriles and furan-2(5H)-one in good overall yields (59-61%).
