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Communication | Regular issue | Vol 6, No. 4, 1977, pp.449-457
Published online, 1st January, 1970
DOI: 10.3987/R-1977-04-0449
Pteridines. Part XLII. Synthesis of Some Banzo[g]pteridines. A Novel Aromatization Reaction

Edward C. Taylor* and John V. Berrier

*Department of Chemistry, Princeton University , Princeton, New Jersey 08544, U.S.A.

Abstract

Condensation of 6-chloro-2-oximinocyclohexanone with aminomalononitrile gave 2-amino-3-cyano-5-chloro-5,6,7,8-tetrahydroqinoxaline 1-oxide (1), which upon heating in acetic acid underwent a novel aromatization reaction, with loss of HCl and H2O, to give 2-amino-3-cyanoquinoxaline (3). An analogous aromatization reaction was observed with 3-amino-2-cyano-5,6-dihydrobenzo(h)quinoxaline 1-oxide (9), which gave 3-amino-2-cyanobenzo(h)quinoxaline (10) upon heating with a trace of HCl or H2SO4. These o-aminonitriles were then converted to variously substituted fused pteridine derivatives by conventional cyclization techniques.