Synthesis and reactions of some heterocyclic azacyanines

K. S. Huang, M. J. Haddadin, M. M. Olmstead, M. J. Kurth

Research output: Contribution to journalArticle

31 Scopus citations

Abstract

The one-step reaction of some amino-substituted heterocycles with diiodomethane to give azacyanines is reported. This useful reaction is of wider application than initially reported and includes the synthesis of new substituted pyrido-, isoquino-, benzimadazo-, and benzothiazoazacyanines 7. Furthermore, treatment of these azacyanines with base generally affects a facile opening of the dihydrotriazinium ring resulting in the formation of new heterocycles 10, 11, and 12, which would be difficult to prepare by other means. This reaction takes an additional direction in the case of halo-substituted azacyanines 7b/c/d where treatment with base gives rise to new interesting derivatives of dipyridotriazines 14b/c/d.

Original languageEnglish (US)
Pages (from-to)1310-1315
Number of pages6
JournalJournal of Organic Chemistry
Volume66
Issue number4
DOIs
StatePublished - Feb 23 2001

ASJC Scopus subject areas

  • Organic Chemistry

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    Huang, K. S., Haddadin, M. J., Olmstead, M. M., & Kurth, M. J. (2001). Synthesis and reactions of some heterocyclic azacyanines. Journal of Organic Chemistry, 66(4), 1310-1315. https://doi.org/10.1021/jo001484k