Enyne cross metathesis of propargylamines with ethyl vinyl ether enables the one-pot synthesis of substituted pyrroles. A series of substituted pyrroles, bearing alkyl, aryl, and heteroaryl substituents, has been synthesized in good yields under microwave irradiation. The reactions are rapid and procedurally simple and also represent a facile entry to the synthetically challenging 1,2,3-substituted pyrroles. The value of the methodology is further corroborated by the conversion of pyrroles into 3-methyl-pyrrolines and the derivatization of the 3-methyl-substituent arising from the metathesis reaction.
Chachignon, H., Scalacci, N., Petricci, E., Castagnolo, D. (2015). Synthesis of 1,2,3-substituted pyrroles from propargylamines via a one-pot tandem enyne cross metathesis-cyclization reaction. JOURNAL OF ORGANIC CHEMISTRY, 80(10), 5287-5295 [10.1021/acs.joc.5b00222].
Synthesis of 1,2,3-substituted pyrroles from propargylamines via a one-pot tandem enyne cross metathesis-cyclization reaction
PETRICCI, ELENA;
2015-01-01
Abstract
Enyne cross metathesis of propargylamines with ethyl vinyl ether enables the one-pot synthesis of substituted pyrroles. A series of substituted pyrroles, bearing alkyl, aryl, and heteroaryl substituents, has been synthesized in good yields under microwave irradiation. The reactions are rapid and procedurally simple and also represent a facile entry to the synthetically challenging 1,2,3-substituted pyrroles. The value of the methodology is further corroborated by the conversion of pyrroles into 3-methyl-pyrrolines and the derivatization of the 3-methyl-substituent arising from the metathesis reaction.File | Dimensione | Formato | |
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https://hdl.handle.net/11365/983031