Ultrasound-promoted synthesis of novel spirooxindolo/spiroacenaphthen dicyano pyrrolidines and pyrrolizidines through regioselective azomethine ylide cycloaddition reaction

被引：40

作者：

Rezaei, Seyed Jamal Tabatabaei ^{[1
]}

Nabid, Mohammad Reza ^{[1
]}

Yari, Ahmad ^{[2
]}

Ng, Seik Weng ^{[3
]}

机构：

[1] Shahid Beheshti Univ, Fac Sci, Dept Chem, Tehran 1983963113, Iran

[2] Univ Tehran, Univ Coll Sci, Sch Chem, Tehran 6455, Iran

[3] Univ Malaya, Dept Chem, Kuala Lumpur 50603, Malaysia

来源：

ULTRASONICS SONOCHEMISTRY | 2011年 / 18卷 / 01期

关键词：

Azomethine ylide; Spirooxindole; Spiroacenaphthen; Ultrasound irradiation; 1,3-Dipolar cycloaddition; Knoevenagel adduct; BAYLIS-HILLMAN ADDUCTS; 1,3-DIPOLAR CYCLOADDITION; FACILE SYNTHESIS; SPIROPYRROLIZIDINES; POLYMERIZATION;

D O I：

10.1016/j.ultsonch.2010.05.016

中图分类号：

O42 [声学];

学科分类号：

070206 ; 082403 ;

摘要：

Novel dicyano functionalised spiropyrrolidine and spiropyrrolizidine were synthesized from the reaction of various arylidenemalononitrile Knoevenagel adducts with non-stabilized azomethine ylides generated from isatin/acenaphthenequinone and sarcosine/N-phenylglycine/proline. The reactions were carried out under both conventional heating and ultrasonic irradiation conditions. In general, improvement in rates and yields were observed when the reactions were carried out under sonication compared with classical conditions. The regio and stereochemistry of the products was established by single crystal X-ray structure and spectroscopic techniques. (C) 2010 Elsevier B.V. All rights reserved.

引用

页码：49 / 53

页数：5

共 31 条

[1]

ABOUGHARBIA MA, 1979, HETEROCYCLES, V12, P637

[2]

[Anonymous], 1984, 1 3 DIPOLAR CYCLOADD

[3] An easy access to novel steroidal dispiropyrrolidines through 1,3-dipolar cycloaddition of azomethine ylides [J].