86734-19-2

Upstream product

• 109-97-7 pyrrole 
• 100-52-7 benzaldehyde 
• 55-21-0 benzamide 
• 3959-05-5 2-bromobenzylamine 
• 98-88-4 benzoyl chloride 
• 54582-33-1 1,1'-carbonyldiimidazole 
• 5145-65-3 N-benzoylpyrrole 
• 220358-42-9 (3S,4S)-N-(o-bromobenzyl)pyrrolidine-3,4-diol 
• 497147-39-4 phenyl-di-pyrrol-1-yl-methanol 
• 220358-48-5 (3S,4S)-N-(o-bromobenzyl)-3,4-diacetoxypyrrolidine 

Downstream Products

• 100-52-7 benzaldehyde 
• 643734-41-2 1-[(tert-butyl-dimethyl-silanyloxy)-phenyl-methyl]-1H-pyrrole 
• 4192-77-2 ethyl cinnamate 
• 109-97-7 pyrrole 

Relevant academic research and scientific papers

A New Chemoselective Base-Mediated Protection/Deprotection Method for Aldehydes

A wide range of aldehydes was efficiently protected as pyrrole carbinol derivatives by direct addition of lithium pyrrolate in THF at -78°C. The protection is chemoselective towards aldehydes over ketones and the O-lithiated, O-protonated or O-silylated carbinols may be used to block the aldehyde from nucleophilic and basic reagents at low temperatures. Mild, basic deprotection using DBU, NaOMe or TBAF allows for in situ trapping-reactions (such as Wadsworth-Horner-Emmons olefination) of the released aldehyde.

Remarkably stable tetrahedral intermediates: Carbinols from nucleophilic additions to N-acylpyrroles

Sufficiently stable intermediates formed in the reaction of N-acylpyrroles (1) with hydride and Grignard reagents can undergo further synthetic transformations and chromatographic purification to enable the generation of pyrrolecarbinols 2 in 76-95% yields [Eq. (1)].

Intramolecular 1,5-hydrogen atom transfer radical reaction of pyrrolidine derivatives

Intramolecular 1,5-hydrogen atom transfer radical cyclization reaction of pyrrolidine derivatives was examined. Radical reaction of 3,4-bis(α,β- unsaturated acyloxy)-(8, 9) and 3,4-diacetoxy (13)-N-[(o- halobenzyl)pyrrolidines underwent elimination of two acyloxy groups to give mainly N-benzylpyrrole (11). On the other hand, the similar reaction of 3,4- diallyloxy-N-(o-bromobenzyl)pyrrolidine (16) gave desired hexahydrofuro[3,2- b]pyrroles (17, 18) together with a dimeric hexahydrofuro[3,2-b]pyrrole (19).

CONVERSION OF PRIMARY AMIDES INTO ACTIVE ACYLATING AGENTS VIA ACYLPYRROLES.

Several primary amides were converted to N-acylpyrroles on reaction with 1,4-dichloro-1,4-dimethoxybutane (1) and Amberlyst A-21 resin.The acylpyrroles act as active acylating agents.