Orthogonal synthesis of pyrroles and 1,2,3-triazoles from vinyl azides and 1,3-dicarbonyl compounds |
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Authors: | Eileen Pei Jian NgYi-Feng Wang Benjamin Wei-Qiang HuiGuillaume Lapointe Shunsuke Chiba |
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Affiliation: | a Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, Singapore 637371, Singapore b Department fur Chemie und Biochemie, Universitat Bern, Freiestrasse 3, CH-3012, Switzerland |
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Abstract: | 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 2H-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 K2CO3, 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. |
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Keywords: | Vinyl azides Pyrroles 1,2,3-Triazoles 1,3-Dicarbonyl compounds |
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