Synthesis of novel tricyclic and tetracyclic sultone scaffolds via intramolecular 1, 3-dipolar cycloaddition reactions

被引：16

作者：

Ghandi, Mehdi ^{[1
]}

Taheri, Abuzar ^{[1
]}

Bozcheloei, Abolfazl Hasani ^{[1
]}

Abbasi, Alireza ^{[1
]}

Kia, Reza ^{[2
,3
]}

机构：

[1] Univ Tehran, Sch Chem, Coll Sci, Tehran, Iran

[2] Islamic Azad Univ, Xray Crystallog Lab, Plasma Phys Res Ctr, Sci & Res Branch, Tehran, Iran

[3] Islamic Azad Univ, Dept Chem, Sci & Res Branch, Tehran, Iran

来源：

TETRAHEDRON | 2012年 / 68卷 / 18期

关键词：

Pyrrolidine; Pyrrolizidine; 1,3-Dipoar cycloaddition; Sultone; DIELS-ALDER REACTION; ENANTIOSELECTIVE 1,3-DIPOLAR CYCLOADDITION; STEREOSELECTIVE-SYNTHESIS; EFFICIENT SYNTHESIS; AZOMETHINE YLIDES; DERIVATIVES; INHIBITORS; NITRONES;

D O I：

10.1016/j.tet.2012.02.053

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The initially prepared 2-formylphenyl-(E)-2-phenylethenesulfonates from the condensation of (E)-2-phenylethenesulfonyl chloride with 2-hydroxybenzaldehyde derivatives underwent intramolecular [3+2] cycloaddition with methyl or phenylhydroxylamine, sarcosine, and L-proline, affording the corresponding novel isoxazolidine, pyrrolidine and pyrrolizidine-annulated gamma,delta-benzo-delta-sultones, respectively, in good yields. Unambiguous assignment of the molecular structures was carried out by single-crystal X-ray diffraction. (C) 2012 Elsevier Ltd. All rights reserved.

引用

页码：3641 / 3648

页数：8

共 56 条

[1]

[Anonymous], 2003, Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products

[2]

Banerji A., 2001, J INDIAN I SCI, V81, P313

[3] Effect of substitution on the intramolecular 1,3-dipolar cycloaddition of alkene tethered munchnones [J].