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Synthesis and structural studies of a new class of heterocyclic compounds : 1,2,4pyridothiadiazine 1,1-dioxides, pyridyl analogues of 1,2,4-benzothiadiazine 1,1-dioxides

par de Tullio, Pascal;Pirotte, Bernard;Dupont, L;Masereel, B;Laeckmann, D;Podona, T;Diouf, O;Lebrun, Philippe ;Delarge, Jacques
Référence Tetrahedron, 51, page (3221-3234)
Publication Publié, 1995

Article révisé par les pairs

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Résumé :

A series of novel 1,2,4-pyridothiadiazine 1,1-dioxides (1), some of them being pyridyl analogues of the 1,2,4-benzothiadiazine 1,1-dioxide diazoxide (2), were synthesized and selected physicochemical data (pKa, log P′) were collected. By means of spectral (13C NMR, UV) and X-ray data, the most favourable position of the C=N double bond in the thiadiazine ring was discussed. It was concluded that like 1,2,4-benzothiadiazine 1,1-dioxides, 1,2,4-pyridothiadiazine 1,1-dioxides free of an alkyl substituent in the 2- and 4-positions, whatever the nitrogen atom position in the pyridine ring, show predominance of the tautomeric 4H-form. © 1995.