102537-10-0

Basic information

• Product Name: 1H-Pyrrole-3,4-dicarboxylic acid, 2-benzoyl-1-methyl-5-phenyl-, dimethyl ester
• CAS NO: 102537-10-0
• Molecular Formula: C22H19NO5
• Molecular Weight: 377.397
• Mol File: 102537-10-0.mol

Chemical Properties

• CAS DataBase Reference: 1H-Pyrrole-3,4-dicarboxylic acid, 2-benzoyl-1-methyl-5-phenyl-, dimethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Pyrrole-3,4-dicarboxylic acid, 2-benzoyl-1-methyl-5-phenyl-, dimethyl ester(102537-10-0)
• EPA Substance Registry System: 1H-Pyrrole-3,4-dicarboxylic acid, 2-benzoyl-1-methyl-5-phenyl-, dimethyl ester(102537-10-0)

Safety Data

• Hazardous Substances Data: 102537-10-0(Hazardous Substances Data)

Upstream product

• 52266-12-3 2-methyl-3,5-diphenyl-2,3-dihydro-1,2-oxazole 
• 23055-10-9 1,4-dimethyl but-2-enedioate 
• 102537-03-1 C₁₆H₁₅NO 
• 762-42-5 dimethyl acetylenedicarboxylate 
• 102537-09-7 (2R,5S)-2-Benzoyl-1-methyl-5-phenyl-2,5-dihydro-1H-pyrrole-3,4-dicarboxylic acid dimethyl ester 
• 6476-40-0 cis-1-methyl-2-benzoyl-3-phenylaziridine 

Relevant articles and documents

Iridium-Catalyzed Cyclization of Isoxazolines and Alkenes: Divergent Access to Pyrrolidines, Pyrroles, and Carbazoles

A heterogeneous iridium-complex-catalyzed N-O-cleaving rearrangement/cyclization of 2,3-dihydroisoxazoles with alkenes has been developed. It provides divergent access to multiple substituted pyrrolidines, pyrroles, and carbazoles. The iridium catalyst remains highly catalytic active after seven cycles. The gram-scale synthesis afforded a carbazole with strong bluish-violet fluorescence.

A Comparison of 4-Oxazoline and 2-Acylaziridine Routes to Azomethine Ylides

Pyrolysis of aziridines 6 or 7 affords azomethine ylides, which can also be generated from 3-methyl-2,5-diphenyl-4-oxazoline (1a) at room temperature.Attempts to trap the thermally generated ylide with dimethyl acetylenedicarboxylate afford increasing amounts of the unusual enamine product 9 as the temperature decreases.The aziridine-derived dipoles (2a or 3a vs 4a or 5a) cannot be trapped prior to equilibration.Similar results are obtained from the aziridines 16/17, but in this case, dipole isomers can be intercepted by N-phenylmaleimide in xylene solution.The 2,3-dimethyl-5-methoxy-4-oxazoline derived dipole 2b probably does not equilibrate, but its 2 + 3 cycloadducts correspond to the major products formed by aziridine pyrolysis under equilibrating conditions.

Nucleophilic Addition to Oxazolium Salts: Stabilized Azomethine Ylides via 2-Substituted 4-Oxazolines

Treatment of oxazolium salts with cyanide generates 4-oxazolines 2 in situ.Ring opening to azomethine ylides 3 occurs spontaneously and 2 + 3 cycloadducts are obtained in the presence of acrylate, propiolate, or acetylenedicarboxylate dipolarophiles.In the case of acetylenic dipolarophiles, loss of HCN occurs under the reaction conditions and leads directly to pyrroles 5.The propiolate experiments are complicated by the formation of six-membered adducts 17 in some cases.This reaction pathway is explained by the addition of the acetylide anion derived from propiolate to the dipole, followed by cyclization.Sulfide nucleophiles can also be used to generate 4-oxazolines, but the yields of cycloadducts are lower.