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Paper | Regular issue | Vol 26, No. 5, 1987, pp.1227-1238
Published online, 1st January, 1970
DOI: 10.3987/R-1987-05-1227
The Synthesis of Two Strongly Electron Deficient Flavin Analogs

Czeslaw Radziejewski, Soumitra Ghosh, and Emil Thomas Kaiser

*Laboratory of Bioorganic, Chemistry Department, Rockefeller University, 1230 York Avenue, New York, NY 10021, U.S.A.

Abstract

The synthesis of 7-chloro-8-acetyl-10-methylisoalloxazine (2a) and 7-cyano-8-acety1-10-merhylisoalloxazine (2b) was accomplished by the condensation of appropriately substituted o-diamines with alloxan under acidic conditions. The presence of the strongly electron withdrawing chlorine and cyano substituents makes these flavin analogs very effective catalysts of the oxidation of N-alkyl-1,4-dihydronicotinamides. Compound 2a was also found to undergo redox reactions with substrates readily forming carbanions (e.g., nitroethane).