Synthesis of polyfunctionalized pyrroles bearing C-2 α-azido side-chains and displacement of the α-azido group by various nucleophiles. Issue 8 (21st February 2018)

• Record Type: Journal Article
• Authors: Kishii, Naomi; Shimadu, Morie; Maruyama, Shun; Tou, Sayuri; Sasaki, Ikuo; Sugimura, Hideyuki
• Is Part Of: Tetrahedron letters. Volume 59:Issue 8(2018)
• Page Start: 776
• Page End: 780
• Publication Date: 2018-02-21
• Subjects: Tetrasubstituted NH pyrroles -- Annulation -- Elimination-addition reaction -- Transition-metal-free process; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2018.01.049
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: Thermal annulation of α, γ-diazido α, β-unsaturated esters and 1, 3-dicarbonyl compounds. Novel substitution of an azido group with a variety of nucleophiles. Facile process to tetrasubstituted pyrroles with novel substitution patterns. Abstract: Tetrasubstituted pyrroles bearing C-2 α-azido side-chains were synthesized employing a new class of diazides, α, γ-diazido α, β-unsaturated esters, and 1, 3-dicarbonyl compounds under simple thermal conditions. Further investigation of the synthetic utility of the obtained pyrroles reveals unexpected displacement of the α-azido group at the C-2 side-chain by a variety of nucleophiles. This two-step process exhibits a broad substrate scope, good functional group tolerance, simple operation, and high reaction efficiency, providing an easy access to polyfunctional pyrroles with novel substitution patterns.