61369-39-9Relevant academic research and scientific papers
Nouvelle voie d'acces aux iso-alloxazines par l'intermediaire d'alkyl-1-amino-2-tetrahydro-1,5,6,7-quinoxaline-3-carbonitriles (ou carboxylate de methyle)
Lacroix, Alain,Schabat, Dominique,Clerin, Daniel,Fleury, Jean-Pierre
, p. 1065 - 1072 (2007/10/02)
A new synthetic approach to iso-alloxazines using 1-alkyl-2-amino-1,5,6,7-tetrahydroquinoxaline-3-carbonitriles (or the corresponding methylcarboxylates) is reported.These key intermediates, accessible in two steps from cyclohexanone-enamines, when treated alkyl(aryl)iso-cyanates, guanidine or alkylchloroformates yield tetrahydro-iso-alloxazine derivatives, which can be dehydrogenated.Thus 3,10-dialkyl, 10-alkyl-3-aryl, 10-alkyl-iso-alloxazines or their 2-imino-4-oxo, 4-imino-2-oxo and 2,4-bisimino derivatives were obtained.The regiospecific aspect of this approach is illustrated by the synthesis of naphto, naphto or dimethyl-7,8 benzo pteridine derivatives.Tautomeric behavior or the tetrahydro intermediates and some limitations of the method are discussed.
