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Pyrrolo[1,4]diazepines, via thermolyse of carbonylazides, and [3,2,2]cyclazines, via Diels-Alder reaction of [f]indolizines, annelated to [1]benzothiophene

Identifieur interne : 001338 ( France/Analysis ); précédent : 001337; suivant : 001339

Pyrrolo[1,4]diazepines, via thermolyse of carbonylazides, and [3,2,2]cyclazines, via Diels-Alder reaction of [f]indolizines, annelated to [1]benzothiophene

Auteurs : Philippe Ohier [France] ; Adam Daïch [France] ; Bernard Decroix [France]

Source :

RBID : ISTEX:65B84F992AD178CBF2BF158F8983CA3E0EEB0ABA

Abstract

Easy access to fused tricyclic pyrrolo[1,2-a][1]benzothieno[2,3-e][1,4]diazepines from the corresponding carbonyl azides by thermolysis in acetic acid is described. Moreover, new [1]benzothieno[2,3(3,2)-f]indolizines were synthesized in one-pot from 2(3)-(2-formylpyrrol-1-ylmethyl)-[1]benzothiophene and with diethyl acetylenedicarboxylate (DEAD) they led regiospecifically to [3,2,2] cyclazines fused to a [1]benzothiophene ring by 1,3-dipolar cycloaddition reaction rather than Diels-Alder adducts.

Url:
DOI: 10.1016/0040-4020(96)00828-9


Affiliations:


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ISTEX:65B84F992AD178CBF2BF158F8983CA3E0EEB0ABA

Le document en format XML

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