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.
Bianchi, L., Giorgi, G., Maccagno, M., Petrillo, G., Scapolla, C., Tavani, C. (2016). On the behavior of bis(sulfonyl)nitrobutadienes towards primary amines: a convenient access to 1-alkyl-2-aryl-4-(phenylsulfonyl)pyrroles. TETRAHEDRON, 72(44), 7050-7058 [10.1016/j.tet.2016.09.044].
On the behavior of bis(sulfonyl)nitrobutadienes towards primary amines: a convenient access to 1-alkyl-2-aryl-4-(phenylsulfonyl)pyrroles
GIORGI, GIANLUCA;
2016-01-01
Abstract
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.
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https://hdl.handle.net/11365/1001760
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