Copper-catalyzed formal [4 + 1] annulation ofN-propargyl ynamides with diketones

Abstract

An efficient copper-catalyzed formal [4 + 1] annulation of N-propargyl ynamides with diketones is described. This protocol enables practical and atom-economic synthesis of valuable pyrrole-substituted dioxoles in generally moderate to...

Catalytic intermolecular hydrofunctionalizations of ynamides

“…[1][2][3][4][5] Because of their unique structural characteristics and potential coordination ability, ynamides have now emerged as versatile building blocks in organic synthesis and a variety of intriguing reactivities have been disclosed. [6][7][8][9][10] Some special topics such as intra- [11][12][13][14][15][16] and inter-molecular annulations, [17][18][19][20][21][22] radical reactions, 23,24 and asymmetric transformations 25,26 have been carefully reviewed in the last few years.…”

Synthesis of a new fluorophore: wavelength-tunable bisbenzo[f]isoindolylidenes

“…Propargylamine is a crucial intermediate in organic synthesis, particularly for propargylamine compounds that possess multiple alkynyl substitutions. 12 Ye, 13 Sahoo, 14 and Gagosz 15 developed a series of powerful methods utilizing propargyl-ynamides to afford heterocyclic compounds, such as pyrrole, pyridine, quinoline, and their derivatives. Dipropargylamine was employed by Trost et al in the construction of the core structure of cyclic 2-vinyl-1-acyl compounds during the total synthesis of (+)-α-kainic acid.…”

Mechanosynthesis of Pyrrole-2-carboxylic Acids via Copper-Catalyzed Spiroannulation/Ring-Opening Aromatization of 4-Arylidene Isoxazol-5-ones with Enamino Esters

“…14 Ye et al achieved a CuBr-catalyzed [4 + 1] annulation of N-propargyl ynamides with diketones and synthesized a series of dioxole-substituted pyrroles. 15 Recently, a novel CuTc-catalyzed trisannulation of α,β-unsaturated ketoximes with 1,3-dicarbonyls and paraformaldehyde to access 2,3disubstituted pyrroles was developed by Duan's group. 16 Meanwhile, the Yang group reported a CuBr-catalyzed selective synthesis of cyclohexanone-fused pyrroles through the substituent-controlled cyclization of O-acyl oximes with cyclic 1,3diones.…”