78394-12-4

Upstream product

• 58364-87-7 C₂₂H₂₄N₄O₄ 
• 101046-33-7 dimethyl 1-benzyl-2,5-dihydro-1H-3,4-pyrroledicarboxylate 
• 86731-89-7 N-benzyl-N-formyl-glycine 
• 762-42-5 dimethyl acetylenedicarboxylate 
• 104143-94-4 benzyl<(phenylthio)methyl><(trimethylsilyl)methyl>amine 
• 53215-95-5 N-(trimethylsilylmethyl)benzylamine 
• 87813-07-8 N-benzyl-N-(cyanomethyl)-N-[(trimethylsilyl)methyl]amine 
• 100-46-9 benzylamine 
• 144964-17-0 N-benzyl-1-(trimethylsilyl)-N-((trimethylsilyl)methyl)methanamine 

Downstream Products

• 92763-89-8 (1-Benzyl-4-hydroxymethyl-1H-pyrrol-3-yl)-methanol 
• 92763-78-5 2,8-Dibenzyl-2H,8H-2,8-diaza-dicyclopenta[b,i]anthracene-5,11-dione 
• 92763-74-1 2-Benzyl-6,7-dihydro-2H-benzo[f]isoindole-5,8-dione 
• 92763-72-9 1-benzyl-1H-pyrrole-3,4-dicarbaldehyde 

Relevant academic research and scientific papers

A New and Efficient Strategy for Non-stabilized Azomethine Ylide via Photoinduced Electron Transfer (PET) Initiated Sequential Double Desilylation

A practical approach for generating non-stabilized azomethine ylide by PTE initiation is generated.

Utilization of Phenylthio Substituted Amines for the Synthesis of Pyrrolidines

α-Phenylthio substituted amines have been found to be convenient reagents for the preparation of the pyrrolidine ring.Benzylamine (2) undergoes 1,3-dipolar cycloaddition with several dipolarophiles in the presence of silver fluoride.The reaction is believed to proceed via the intermediacy of an azomethine ylide.Treatment of α-(phenylthio)cyanoamines 10 and 17 with strong base results in the loss of the phenylthio group, and formation of substituted trans-piperazines 21, 22 in the case of 17.The mechanism of the reaction involves dimerization of the initially formed cyano substituted azomethine ylide intermediate, which behaves as a captodative diradical.Finally, the reaction of several alkenylamines with tributyltin hydride was studied as a method for generating the pyrrolidine ring via a radical cyclization reaction.

Synthetic Application of Cyanoaminosilanes as Azomethine Ylide Equivalents

A series of α-cyanoaminosilanes have been found to act as azomethine ylide equivalents.Treatment of these compounds with silver fluoride in the presence of electron-dificient alkynes and olefins gives substituted pyrroles and pyrrolidines in high yield.It was found that N-benzyl-N-(cyanomethyl)-N-amine undergoes stereospecific cycloaddition with dimethyl fumarate and maleate.The stereospecificity of the reaction is consistent with a concerted cycloaddition reaction.The cycloaddition behavior of an unsymmetrically substituted α-cyanosilylamine with methyl propiolate was also examined and found to react with high overall regioselectivity.The synthetic utility of cyanoaminosilanes as azomethine ylide equivalents was demonstrated by the preparation of a Reniera isoindole alkaloid.The key step in the synthesis involved the reaction of 2-methyl-3-methoxyquinone with N-methyl-N-(cyanomethyl)-N-amine in the presence of silver fluoride to give 2,5-dimethyl-6-methoxy-2H-isoindole-4,7-dione in good yield.

PHOTOLYSIS OF A 2-TETRAZENE FROM AN ENEHYDRAZINE

Photolysis of the 2-tetrazene 1 gives the triazole 2 by homolysis of one single N,N-bond.The formation of the other products 4 - 13 can be rationalized by regarding the aza-allyl radical 3 as a common precursor.