Probing the reactivity of nebularine N1-oxide. A novel approach to C-6 C-substituted purine nucleosides |
| |
Authors: | Stefano D’ErricoVincenzo Piccialli Giorgia Oliviero Nicola BorboneJussara Amato Valentina D’AtriGennaro Piccialli |
| |
Institution: | a Dipartimento di Chimica delle Sostanze Naturali, Università degli Studi di Napoli Federico II, Via D. Montesano 49, 80131 Napoli, Italy b Dipartimento di Chimica Organica e Biochimica, Università degli Studi di Napoli Federico II, Via Cynthia 4, 80126 Napoli, Italy c Facoltà di Scienze Biotecnologiche, Università degli Studi di Napoli Federico II, Via D. Montesano 49, 80131 Napoli, Italy |
| |
Abstract: | A novel approach to the synthesis of purine nucleoside analogues, featuring the reaction of the C6-N1-O− aldonitrone moiety of 9-ribosyl-purine (nebularine) N1-oxide with some representative dipolarophiles, as well as Grignard reagents, is reported. Addition of Grignard reagents to the electrophilic C-6 carbon of the substrate allows a facile access to C-6 C-substituted purine nucleosides without using metal catalysts. 1,3-Dipolar cycloaddition processes lead to novel nucleoside analogues via opening, degradation or ring-enlargement of the pyrimidine ring of the base system of the first-formed isoxazoline or isoxazolidine cycloadduct. |
| |
Keywords: | |
本文献已被 ScienceDirect 等数据库收录! |
|