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Paper | Regular issue | Vol 48, No. 9, 1998, pp.1833-1840
Published online, 1st January, 1970
DOI: 10.3987/COM-98-8216
A Novel Tetracyclic System Containing the 1,2,6-Thiadiazine Ring: Synthesis, Structural Assignment and Tautomeric Studies

Nuria Campillo, Angeles de la Cruz, Pilar Goya, and Juan A. Páez*

*Instituto de Química Médica, C. S. I. C., Calle Juan de Cierva, 3, E-28006 Madrid, Spain

Abstract

Condensation of 3,4,5-triamino-2H-1,2,6-thiadiazine 1,1-dioxide with phthalaldehyde afforded a tetracyclic system of thiadiazino[3’,4’:4,5]imidazo[2,1-a]isoindole 2,2-dioxide. In order to establish the correct structure it was necessary to use an 15N-labelled thiadiazine derivative as starting material. Ab initio theoretical calculations and the Onsager model have been used to study annular tautomerism in this novel structure.