SYNTHESIS AND THERMAL REARRANGEMENT OF 2-ALKOXYCARBONYL-3-ALKYL-4H-BENZO[b][1,4]THIAZINES |
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| Authors: | Paolo Marchini Giuseppe Trapani Gaetano Liso Vincenza Berardi |
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| Institution: | Istituto di Chimica Organica della Facolta' di Farmacia , Universita' di Bari , Bari, Italy |
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| Abstract: | Abstract The title compounds (4b-d) together with the benzothiazolines (5b-d) have been obtained by a reaction between 2,2′-dithiodianiline (1) and β-keto esters (2b-d). The reaction between 1 and the β-keto ester 2a gives 1,4-benzothiazine 3a in addition to the benzothiazoline 5a. It has been established that the 1,4-benzothaizines 4b-d undergo an acid-catalysed thermal rearrangement involving a 1,3] shift of the sulfur atom, giving rise to the isomeric 1,4-benzothiazines 3b-d. |
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