Regio- and stereoselective synthesis of new spiro-isoxazolidines via 1,3-dipolar cycloaddition

被引：8

作者：

Jegham, Nafaa ^{[1
]}

Bahi, Amira ^{[1
]}

El Guesmi, Nizar ^{[2
,3
]}

Kacem, Yakdhane ^{[1
]}

Ben Hassine, Bechir ^{[1
]}

机构：

[1] Fac Sci Monastir, Lab Synth Organ Asymetr & Catalyse Homogene 01UR1, Ave Environm, Monastir 5000, Tunisia

[2] Fac Sci Monastir, Dept Chim, Ave Environm, Monastir 5000, Tunisia

[3] Umm Alqura Univ, Fac Appl Sci, Dept Chem, POB 9569, Mecca, Saudi Arabia

来源：

ARABIAN JOURNAL OF CHEMISTRY | 2017年 / 10卷

关键词：

1,3-Dipolar cycloaddition; Isoquinolinediones; Nitrones; Regiochemistry; Stereoselective; Spiroisoxazolidines; ARYL-N-PHENYLNITRONES; ARYLNITRILE OXIDES; NITRONES;

D O I：

10.1016/j.arabjc.2014.05.028

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

New spiro-isoquinolinediones were prepared by regio- and stereoselective 1,3-dipolar cycloaddition of (E)-4-arylidene-N-methyl-isoquinoline-1,3-dione derivatives 1a-d with C-aryl-N-phenylnitrones 2e-g. NMR studies confirmed that only one regioisomer was formed selectively in the majority of cases. Regioselectivity of the reaction was established by H-1 and C-13 NMR assignments. The stereochemistry of spirannic compounds 3a-l and 4a-c has been corroborated by means of DFT calculations. The structures of all the products were characterized thoroughly by NMR and elemental analyses. (C) 2014 King Saud University. Production and hosting by Elsevier B.V.

引用

页码：S3889 / S3894

页数：6

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