Orthogonal synthesis of pyrroles and 1,2,3-triazoles from vinyl azides and 1,3-dicarbonyl compounds

Tri- and tetrasubstituted N–H pyrroles were prepared by the simple treatment of vinyl azides with 1,3-dicarbonyl compounds in toluene at 100 °C via 2 H-azirine intermediates generated in situ. When the reactions of vinyl azides and 1,3-dicarbonyl compounds were performed in DMF in the presence of a...

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Bibliographic Details
Published in:Tetrahedron 2011-10, Vol.67 (40), p.7728-7737
Main Authors: Ng, Eileen Pei Jian, Wang, Yi-Feng, Hui, Benjamin Wei-Qiang, Lapointe, Guillaume, Chiba, Shunsuke
Format: Article
Language:English
Subjects:
1,2,3-Triazoles
1,3-Dicarbonyl compounds
Catalysis
Catalysts
Chemical reactivity
Chemistry
Cycloaddition
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings
Organic chemistry
Preparations and properties
Pyrroles
Reactivity and mechanisms
Synthesis (chemistry)
Tetrahedrons
Toluene
Vinyl azides
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Summary:Tri- and tetrasubstituted N–H pyrroles were prepared by the simple treatment of vinyl azides with 1,3-dicarbonyl compounds in toluene at 100 °C via 2 H-azirine intermediates generated in situ. When the reactions of vinyl azides and 1,3-dicarbonyl compounds were performed in DMF in the presence of a catalytic amount of K 2CO 3, 1-vinyl-1,2,3-triazoles were obtained via 1,3-dipolar cycloaddition. These methodologies exploited orthogonal modes of chemical reactivity of vinyl azides, which could be achieved by slight modification of the reaction conditions. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2011.08.006