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
收藏
页码：5553 / 5556
页数：4
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