Regiochemistry of the Condensation of 2-Aroyl-cyclohexanones and 2-Cyanoacetamide: 13C-Labeling Studies and Semiempirical MO Calculations

OPJ van Linden, M Wijtmans, L Roumen…

文献索引：Van Linden, Oscar P. J.; Wijtmans, Maikel; Roumen, Luc; Rotteveel, Lonneke; Leurs, Rob; De Esch, Iwan. J. P. Journal of Organic Chemistry, 2012 , vol. 77, # 17 p. 7355 - 7363

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被引用次数: 2

摘要

Hydroxy-aryl-5, 6, 7, 8-tetrahydroisoquinoline-4-carbonitriles represent interesting chemical scaffolds, but synthetic access to these compounds is limited. The reaction of 2-aroyl- cyclohexanones with 2-cyanoacetamide and base in ethanol has been reported to lead to the formation of the tetrahydroisoquinoline isomer. We show that depending on the electronic nature of the para-substituent on the aryl ring, formation of the regioisomeric ...