Journal of Sulfur Chemistry p. 171 - 178 (2012)
Update date:2022-08-02
Topics:
Gupta, Aarti
Devi, Pragati
Kishore, Dharma
An expedient protocol for the synthesis of face b pyrido-annulated analogs of 1,5-benzothiazepines, namely 4-(methylthio)-5-(1,3,4-oxadiazol-2-yl)-2- phenyl-5,11-dihydrobenzo[b] pyrido[2,3-e] [1,5] thiazepine-S,S-dioxides 9a-9f, of medicinal interest emerged to exploit the potential of 3-ketene dithioacetal-substituted derivatives of 4-(1,3,4-oxadiazol-2-yl)-2,3- dihydrobenzo[b] [1,5] thiazepin-2(1H)-one-S,S-dioxide 8. This latter compound 8 was obtained from the base-catalyzed condensation of CS2 x2032;,4′- oxadiazol-2′-yl)-2,3-dihydrobenzo[b] [1,5] thiazepin-2(1H)-one-S,S-dioxide (7). Compound 7 was available from ethyl-2-oxo-2,3,4,5-tetrahydro-[1,5]- benzothiazepin-4-carboxylate (3) on applying established synthetic procedures, which had been previously employed in the literature on related substrates. Treatment of 8 with the anions derived from substituted acetophenones formed the diones which underwent facile cyclocondensation with NH4OAc in AcOH to yield the desired products 9a-9f in acceptable yields.
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