Synthesis of new aza-bicyclic 2-isoxazolines by 1,3-dipolar cycloaddition of endocyclic enecarbamates and enamides with nitrile oxides

被引：8

作者：

de Almeida, Valderes Moraes ^{[1
]}

dos Santos, Rosiel Jose ^{[1
]}

da Silva Goes, Alexandre Jose ^{[2
]}

de Lima, Jose Gildo ^{[1
]}

Duarte Correia, Carlos Roque ^{[3
]}

de Faria, Antonio Rodolfo ^{[1
]}

机构：

[1] Univ Fed Pernambuco, Dept Ciencias Farmaceut, LASOF, BR-50470521 Recife, PE, Brazil

[2] Univ Fed Pernambuco, Dept Antibiot, BR-50560901 Recife, PE, Brazil

[3] Univ Estadual Campinas, Inst Quim, BR-13083970 Campinas, SP, Brazil

来源：

TETRAHEDRON LETTERS | 2009年 / 50卷 / 06期

关键词：

Endocyclic enecarbamates; Enamides; 1,3-Dipolar cycloaddition; Nitrile oxides; 2-Isoxazolines; GEISSMAN-WAISS LACTONE; ENANTIOSELECTIVE SYNTHESIS; DIAZONIUM SALTS; HECK ARYLATION; DERIVATIVES; INHIBITORS; EFFICIENT; KETENES;

D O I：

10.1016/j.tetlet.2008.11.096

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Novel aza-bicyclic 2-isoxazolines, 4,5-dihydroisoxazole[5,4-b]pyrrolidines, and 4,5-dihydroisoxazole[5,4b]piperidines were synthesized in a highly regioselective manner through a 1,3-dipolar cycloaddition reaction of 5- and 6-membered endocyclic enecarbamates and enamides with several nitrile oxides in good to excellent yields. Hydrogenolysis of 5- and 6-membered Cbz-cycloadducts led to secondary amines, which presented distinctive stabilities. 2-Isoxazoline bisamides were obtained in good yields through a N-benzoylation, followed by ammonolysis of the secondary amine, or directly from ammonolysis of the cycloadducts. (C) 2008 Elsevier Ltd. All rights reserved.

引用

页码：684 / 687

页数：4

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