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 (x-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 hexahydro[1]pyrindin-7-ones and 3,4,5,6,7,8-hexahydro-(2H)-cyclopenta[b]azepin-8-ones. This methodology represents a novel and efficient procedure for the preparation of these classes of azacyclic compounds.
Synthesis of a-Acyl Functionalized Azacycles by Pd-Catalyzed Cross-Coupling Reactions of a-Alkoxyboronates with Lactam-derived Vinyl Triflates / E. OCCHIATO; C. PRANDI; A. FERRALI; A. GUARNA; A. DEAGOSTINO; P. VENTURELLO. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - STAMPA. - 67:(2002), pp. 7144-7146. [10.1021/jo025930a]
Synthesis of a-Acyl Functionalized Azacycles by Pd-Catalyzed Cross-Coupling Reactions of a-Alkoxyboronates with Lactam-derived Vinyl Triflates
OCCHIATO, ERNESTO GIOVANNI;GUARNA, ANTONIO;
2002
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 (x-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 hexahydro[1]pyrindin-7-ones and 3,4,5,6,7,8-hexahydro-(2H)-cyclopenta[b]azepin-8-ones. This methodology represents a novel and efficient procedure for the preparation of these classes of azacyclic compounds.File | Dimensione | Formato | |
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