60295-09-2

Upstream product

• 870-46-2 t-butoxycarbonylhydrazine 
• 122-00-9 para-methylacetophenone 
• 1070-19-5 N-(tert-butyloxycarbonyl) azide 

Downstream Products

• 1198575-39-1 1,6-dimethyl-3,4-diphenyl-isoquinoline 
• 65241-92-1 5-(4-methylphenyl)-2,3-diphenyl-1H-pyrrole 
• 1613470-82-8 1,4,6-trimethyl-3-phenylisoquinoline 
• 21399-31-5 2-(4-methylphenyl)-5-phenyl-1H-pyrrole 
• 1613470-77-1 3,4-bis(4-methoxyphenyl)-1,6-dimethylisoquinoline 
• 1613470-76-0 1,6-dimethyl-3,4-di(p-tolyl)isoquinoline 
• 60295-19-4 N'-(1-p-Tolyl-ethyl)-hydrazinecarboxylic acid tert-butyl ester 

Relevant academic research and scientific papers

Rhodium-Catalyzed Oxidative Cycloaddition of N-tert-Butoxycarbonylhydrazones with Alkynes for the Synthesis of Functionalized Pyrroles via C(sp3)–H Bond Functionalization

A rhodium(III)-catalyzed cycloaddition of N-tert-butoxycarbonylhydrazones with internal alkynes was developed. The reaction features a regioselective α-imino alkyl C(sp3)?H bond functionalization resulting in selective formation of highly functionalized NH-free pyrroles. Our studies showed that utilizing the N-tert-butoxycarbonyl (N-Boc) as the oxidizing directing group is critical for achieving the observed pyrrole formation versus the isoquinoline formation. To account for the pyrrole formation, we hypothesized that a prior tautomerization of the N-Boc-hydrazones to enamines should occur, followed by regioselective C(sp2)–H cleavage to form a putative five-membered rhodacycle. Subsequent coupling of the rhodacycle with the alkynes would afford the pyrrole products. (Figure presented.).