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 : 001339Pyrrolo[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 :
- Tetrahedron [ 0040-4020 ] ; 1996.
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:
Links toward previous steps (curation, corpus...)
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- to stream Main, to step Curation: 001E64
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ISTEX:65B84F992AD178CBF2BF158F8983CA3E0EEB0ABALe document en format XML
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<front><div type="abstract" xml:lang="en">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.</div>
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