82430-59-9

Upstream product

• 91476-92-5 1-[3-(2,4,6-Trimethyl-phenyl)-3a,8b-dihydro-isoxazolo[4,5-b]indol-4-yl]-ethanone 
• 13307-67-0 ethyl 1H-indole-1-carboxylate 
• 2904-57-6 mesitylenecarbonitrile oxide 
• 576-15-8 N-acetylindole 
• 91476-95-8 Phenyl-[3-(2,4,6-trimethyl-phenyl)-3a,8b-dihydro-isoxazolo[4,5-b]indol-4-yl]-methanone 
• 91477-00-8 3-(2,4,6-Trimethyl-phenyl)-3a,8b-dihydro-isoxazolo[4,5-b]indole-4-carboxylic acid methyl ester 
• 82414-23-1 3-(2,4,6-Trimethyl-phenyl)-3a,8b-dihydro-isoxazolo[4,5-b]indole-4-carboxylic acid ethyl ester 
• 1496-76-0 N-benzoylindole 
• 39203-20-8 methyl 1H-indole-1-carboxylate 

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.