Synthesis of alpha-acyl-functionalized azacycles by Pd-catalyzed cross-coupling reactions of alpha-alkoxyboronates with lactam-derived vinyl triflates |
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Authors: | Occhiato Ernesto G Prandi Cristina Ferrali Alessandro Guarna Antonio Deagostino Annamaria Venturello Paolo |
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Institution: | Dipartimento di Chimica Organica U. Schiff and ICCOM, Università di Firenze, Via della Lastruccia 13, I-50019 Sesto Fiorentino, Italy. ernesto.occhiato@unifi.it |
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Abstract: | Alkoxydienyl- and alkoxystyrylboronates were used for Pd-catalyzed cross-coupling reactions with lactam-derived vinyl triflates. The hydrolysis of the coupling products with alkoxystyrylboronates provided the corresponding alpha-acyl-substituted 3,4-dihydro-(2H)-pyridines and 2,3,4,5-tetrahydroazepines in good to high yields. The hydrolysis of the coupling products with alkoxydienylboronates, performed in the presence of Amberlyst 15, resulted in a Nazarov-type cyclization that afforded hexahydro1]pyrindin-7-ones and 3,4,5,6,7,8-hexahydro-(2H)-cyclopentab]azepin-8-ones. This methodology represents a novel and efficient procedure for the preparation of these classes of azacyclic compounds. |
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