89649-54-7

Upstream product

• 23652-59-7 4-(pyrrolidin-1-yl)pent-3-en-2-one 
• 1118-66-7 4-amino-3-penten-2-one 
• 18709-45-0 methyl 3-phenyl-2H-azirine-2-carboxylate 
• 18803-02-6 5-methoxy-3-phenylisoxazole 
• 123-54-6 acetylacetone 
• 89649-23-0 3'-Acetyl-2'-methyl-4'-phenyl-2,3,4,5,2',3'-hexahydro-1'H-[1,2']bipyrrolyl-5'-carboxylic acid methyl ester 

Relevant academic research and scientific papers

Domino transformation of isoxazoles to 2,4-dicarbonylpyrroles under Fe/Ni relay catalysis

The domino reaction of 5-alkoxy- or 5-aminoisoxazoles, under metal relay catalysis, with symmetric 1,3-diketones gives 4-acylpyrrole-2-carboxylic acid derivatives in high yield. Esters and amides of acylacetic acids react regioselectively, giving derivati

Ambivalent role of metal chlorides in ring opening reactions of 2H-azirines: Synthesis of imidazoles, pyrroles and pyrrolinones

2H-Azirines were found to react with imines, enaminones and enaminoesters in the presence of metal salts. Imidazoles, pyrroles and new pyrrolinones derivatives are isolated in good overall yields. The role of metal salts was investigated as they can act as Lewis acids or electron donors. Mechanisms are proposed suggesting that imidazoles arise from addition of azirine to imines via radical or ionic mechanism; pyrroles and pyrrolinones are obtained from azirines with enamino derivatives when the salt acts as a Lewis acid. In the latter case the properties of the metallic compound influence the reaction regioselectivity.

The Synthesis and Chemistry of Azolenines. Part 2. A General Synthesis of Pyrrole-2-carboxylic Acid Derivatives by the Reaction of 2H-Azirines with Enamines, and the Crystal and Molecular Structure of Ethyl 3-Phenyl-4,5,6,7-tetrahydroindole-2-carboxylate

A new general synthesis of 1H-pyrrole-2-carboxylic acid derivatives is described.Reaction between appropriately substituted 2H-azirines and enamines gives a mixture of 2,3- and 3,4-dihydropyrroles, which on acid treatment yields the title compounds in mod