PMID: 11312961Apr 21, 2001Paper

Synthesis and reactions of some heterocyclic azacyanines

The Journal of Organic Chemistry
K S HuangM J Kurth

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.

Citations

Mar 10, 2010·Proceedings of the National Academy of Sciences of the United States of America·Eric D HorowitzNicholas V Hud
Jan 27, 2016·Chemical Reviews·Gabriella CavalloGiancarlo Terraneo
Oct 21, 2015·Organic & Biomolecular Chemistry·Mariusz TasiorDaniel T Gryko
Jul 8, 2008·Chembiochem : a European Journal of Chemical Biology·Ozgül Persil CetinkolNicholas V Hud
Apr 24, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Georgeta Serban
Feb 26, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Georgeta Serban
Aug 2, 2011·Chembiochem : a European Journal of Chemical Biology·Ragan BuckleyNicholas V Hud
Sep 22, 2020·ACS Omega·Kübra DoğanÖzgül Persil Çetinkol

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