Molecular structure and13C chemical shift assignments of 10-(2′-pyridyl)pyrido[3,2-b][1,4]benzothiazine using 10-phenylpyrido[3,2-b][1,4]benzothiazine as the model compound

Autor: Patrice De Meester, Shirley S. C. Chu, Edward R. Biehl, Misa V. Jovanovic
Rok vydání: 1985
Předmět:
Zdroj: Journal of Heterocyclic Chemistry. 22:777-783
ISSN: 1943-5193
0022-152X
DOI: 10.1002/jhet.5570220333
Popis: The crystal structure of 10-(2′-pyridyl)pyrido[3,2-b][1,4]benzothiazine, 6, shows that orientation of the 10-pyridyl ring is in the plane bisecting the pyridobenzothiazine ring. This orientation is in contrast to that of 10-(2′-pyridyl)phenothiazine, 11, in which the heterocyclic ring is perpendicular to the plane bisecting the phenothiazine nucleus. X-ray data also indicate that the resonance interaction between the lone pair of electrons of NSUB10 in 6 with either the pyridine protons of the tricylcic ring or the 10-(2′-pyridyl) ring is not significant. The folding angle of 166.1° in 6 is the largest observed for the pyridobenzothiazine ring. The nmr spectral assignments of the titled compound, 6, was accomplished using the structurally similar, 10-phenylpyrido[3,2-b][1,4]benzothiazine, 9, as the model compound. 10-(2′-Pyridyl)phenothiazine, 11, was shown to be an inadequate model for such assigments.
Databáze: OpenAIRE
Externí odkaz: