On the behavior of bis(sulfonyl)nitrobutadienes towards primary amines: a convenient access to 1-alkyl-2-aryl-4-(phenylsulfonyl)pyrroles

The conjugated bis(sulfonyl)nitrobutadienes 1 undergo, with primary amines, competitive MeSO2 replacement [vinylic substitution at C(1)] versus aza-Michael addition to the nitroethenyl C(3)–C(4) double bond. The latter pathway eventually leads to the trisubstituted pyrroles 2 and conditions have bee...

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Bibliographic Details
Published in:Tetrahedron 2016-11, Vol.72 (44), p.7050-7058
Main Authors: Bianchi, Lara, Giorgi, Gianluca, Maccagno, Massimo, Petrillo, Giovanni, Scapolla, Carlo, Tavani, Cinzia
Format: Article
Language:English
Subjects:
Michael additions
Nitrobutadienes
Nitrogen heterocycles
Pyrroles
Vinylic nucleophilic substitutions
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Summary:The conjugated bis(sulfonyl)nitrobutadienes 1 undergo, with primary amines, competitive MeSO2 replacement [vinylic substitution at C(1)] versus aza-Michael addition to the nitroethenyl C(3)–C(4) double bond. The latter pathway eventually leads to the trisubstituted pyrroles 2 and conditions have been optimized in order to maximize the yield of such polyfunctionalized heterocycles. Interestingly, in trifluoroethanol tetrasubstituted pyrroles 7 are also formed, thanks to a final aromatization via oxidation by ‘endogenous’ nitrite. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2016.09.044