A convenient CeCl3•7H2O/NaI-promoted synthesis of structurally novel and strained tricyclic β-lactams from hydrazines

被引：14

作者：

Yadav, Lal Dhar S. ^{[1
]}

Rai, Vijai K. ^{[1
]}

机构：

[1] Univ Allahabad, Dept Chem, Green Synth Lab, Allahabad 211002, Uttar Pradesh, India

来源：

TETRAHEDRON LETTERS | 2008年 / 49卷 / 38期

关键词：

beta-lactams; antibiotics; trinems; CeCl3 center dot 7H(2)O/NaI catalysis; hydrazines; 1,3,4-oxadiazoles; thiazoles;

D O I：

10.1016/j.tetlet.2008.07.068

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A convenient synthetic protocol for structurally novel and strained highly derivatized tricyclic beta-lactams has been developed. The synthesis involves CeCl3 center dot 7H(2)O/NaI catalyzed addition-condensation of mercaptoacetic acid and N-aroyl-N'-arylidenehydrazines followed by intramolecular cyclodehydration to afford bicyclic 5H-thiazolo[4,3-b][1,3,4]-oxadiazoles, which on treatment with acid chlorides in the presence of triethylamine furnish highly derivatized tricyclic 3H-azetidino[2,1-b]-thiazolo[3,4-d][1,3,4]-oxadiazol-6-ones in 80-93% yields. The process presents an excellent illustration of Ce(III)-catalyzed C-C, C-N and C-S bond formation in a one-pot procedure. (C) 2008 Elsevier Ltd. All rights reserved.

引用

页码：5553 / 5556

页数：4