112372-20-0Relevant articles and documents
Facile Rearrangement of 2-Amino-3-carbethoxy-4-ethylfuropyridinium Cation to 2-Oxo-3-cyano-4-ethyl-4H-furopyridine
Desideri, N.,Manna, F.,Stein, M. L.
, p. 333 - 335 (2007/10/02)
The rearrangement of 2-amino-3-carbethoxy-4-ethylfuropyridinium iodide in basic solution was studied.The reaction product is 2-oxo-3-cyano-4-ethyl-4H-furopyridine which was obtained also by alkylation with ethyl iodide and sodium hydride in dimethylformamide of 2-oxo-3-cyano-3H-furopyridine or of p-nitrophenyl-3-acetoxypyridine-2-cyanacetate.
Furopyridines. VII. Preparation and Hydrolysis of 2-Cyano and 3-Cyano Derivatives of Furo-, Furo-, and Furopyridine
Morita, Hiroyuki,Shiotani, Shunsaku
, p. 373 - 376 (2007/10/02)
This paper describes the preparation and hydrolysis of 2-cyano and 3-cyano derivatives of furo-, furo-, and furopyridine.Treatment of furopyridines 1a, 1b and 1c with n-butyllithium in hexane-tetrahydrofuran at -70 deg C and subsequent addition of N,N-dimethylformamide yielded 2-formyl derivatives 2a, 2b and 2c.Dehydration of the oximes 4a, 4b and 4c of 2a, 2b and 2c gave 2-cyano compounds 5a, 5b and 5c, which were hydrolyzed to give 2-carboxylic acids, 6a, 6b and 6c, respectively.Reaction of 3-bromo compounds 7a, 7b and 7c with copper(I) cyanide in N,N-dimethylformamide afforded 3-cyano derivatives 8a, 8b and 8c.Alkaline hydrolysis of 8a, 8b and 8c gave compounds formed by fission of the 1-2 bond of furopyridines 9a, 9b and 9c, while acidic hydrolysis gave the corresponding carboxamides, 10a, 10b and 10c.