ChemInform Abstract: A Novel Tandem Sequence to Pyrrole Syntheses by 5‐endo‐dig Cyclization of 1,3‐Enynes with Amines.

Abstract

A new approach to highly substituted pyrroles by using 1,3‐enynes and primary amines in the presence of excess iodine is developed.

Tosyl/pyrrolyl-capped 1,3-enynes via t-BuOK-assisted reaction of TosMIC with acylethynylpyrroles: a new feature of this popular reagent

“…Such transformations cover reductive coupling with carbonyl compounds and imines, 2 hydrostannylation, 3 1,4-alkylarylation 4 and 1,4-alkylcyanation, including 1,4-fluoroalkylcyanation, 5 1,4-sulfimidocyanation, 5 hydroboration, 6 and hydroamination. 7 Substituted 1,3-enynes are also employed for the synthesis of heterocyclic compounds, such as pyrroles, 8 indolines, 9 and furans, 10 and g-lactones featuring a-phosphorus ylides, 11 as well as bicyclic aromatic and heteroaromatic products. 12 Considering the importance of functionalized 1,3-enynes for organic synthesis, significant efforts have been made to develop efficient methods for their synthesis.…”