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Synthesis of novel 1,3,4-benzotriazepine derivatives from 4-oxo-3,1-benzoxazine and 3,1-benzothiazine-2-carbonitriles |
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| Authors: | Franç ois-René Alexandre,Amaya Berecibar,Roger Wrigglesworth,Jean Guillon,Valé rie Thié ry |
| Affiliation: | a Laboratoire de Biotechnologies et Chimie Bio-organique, FRE CNRS 2766, UFR Sciences Fondamentales et Sciences pour l'Ingénieur, Bâtiment Marie Curie, Université de La Rochelle, F-17042 La Rochelle cedex 1, France b PFIZER Global Research & Development, Fresnes Laboratories, 3-9 rue de la Loge, BP100, F-94265 Fresnes cedex, France c EA 2962-Pharmacochimie, UFR de Pharmacie, Université Victor Segalen Bordeaux 2, 146, rue Léo Saignat, 33076 Bordeaux Cedex, France |
| Abstract: | Synthesis of novel oxygen and sulfur containing 1,3,4-benzotriazepine derivatives was performed via 3,1-benzoxazine and 3,1-benzothiazine intermediates obtained from Appel's salt chemistry. We observed that the sulfur containing precursors reacted differently than their oxygenated congeners and, after rearrangement, afforded novel heterocyclic compounds (e.g., benzoxazin-4-thione and 2-cyano-1,3,4-triazepine). |
| Keywords: | 1,3,4-Triazepines 3,1-Benzoxazines 3,1-Benzothiazines 4,5-Dichloro-1,2,3-dithiazolium chloride (Appel's salt) |
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