Tetrahedron

Selectivity in cycloadditions-IX: Cycloadditions of nitrile oxides to indoles. Reactivity and regiochemistry

P Caramella, AC Corsico, A Corsaro, D Del Monte…

文献索引：Caramella, P; Corsico, A. Coda; Corsaro, A; Del Monte, D.; Albini, F. Marinone Tetrahedron, 1982 , vol. 38, # 1 p. 173 - 182

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被引用次数: 33

摘要

Cycloadditions of benzonitrile oxide and mesitonitrile oxide to N-methylindole and indole yield the acid sensitive cycloadducts 1 ad 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 ...