Synthesis of methyleneisoxazolidine nucleoside analogues by microwave assisted nitrone cycloaddition

被引：15
作者：
Chiacchio, Ugo
Corsaro, Antonino
Lannazzo, Daniela
Piperno, Anna
Romeo, Giovanni
Romeo, Roberto
Saita, Maria G.
Rescifina, Antonio
机构：
[1] Univ Catania, Dipartimento Sci Chim, I-95125 Catania, Italy
[2] Univ Messina, Dipartimento Farmacochim, I-98168 Messina, Italy
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2007年 / 2007卷 / 28期
关键词：
1,3-dipolar cycloaddition; nucleosides; microwave irradiation; semiempirical calculations;
D O I：
10.1002/ejoe.200700171
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A new series of conformationally locked N,O-nucleoside analogues was synthesized by exploiting allenic nucleobases as dipolarophiles in 1,3-dipolar nitrone cycloadditions. The regio- and sitoselectivity of the reaction were rationalized according to the frontier orbital treatment of the nitrone cycloaddition by AM1 calculations. (C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)
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页码：4758 / 4764
页数：7
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