82414-16-2

Upstream product

• 13307-67-0 ethyl 1H-indole-1-carboxylate 
• 2904-57-6 mesitylenecarbonitrile oxide 
• 64-17-5 ethanol 
• 91476-99-2 3-(2,4,6-Trimethyl-phenyl)-3a,8a-dihydro-isoxazolo[5,4-b]indole-8-carboxylic acid methyl ester 

Downstream Products

• 91477-22-4 N-methoxycarbonyl-N'(2,4,6-trimethylphenyl)indole-3-carboxamide 
• 91477-23-5 N-ethoxycarbonyl-N'(2,4,6-trimethylphenyl)indole-3-carboxamide 
• 82414-28-6 (1H-Indol-3-yl)-(2,4,6-trimethyl-phenyl)-methanone oxime 
• 82414-32-2 N(2,4,6-trimethylphenyl)indole-3-carboxamide 
• 91476-99-2 3-(2,4,6-Trimethyl-phenyl)-3a,8a-dihydro-isoxazolo[5,4-b]indole-8-carboxylic acid methyl ester 

Relevant academic research and scientific papers

SELECTIVITY IN CYCLOADDITIONS-IX CYCLOADDITIONS OF NITRILE OXIDES TO INDOLES. REACTIVITY AND REGIOCHEMISTRY

Cycloadditions of benzonitrile oxide and mesitonitrile oxide to N-methylindole and indole yield the acid sensitive cycloadducts 1 a-d with high regioselectivity.With N-carbethoxyindole the stable cycloadducts 1 e,f and minor amounts of the regioisomeric 2 e,f are isolated.The electron withdrawing substituent reduces both the regioselectivity and the reactivity of the cycloadditions.Frontier orbital considerations, based on MINDO/3 calculations, allow elucidation of the observed changes in reactivity and regiochemistry.