Nitroimidazoles, part 1.: An unexpected reactivity during the cyclization of 3-(4-amino-1-benzyl-2-ethyl-1H-imidazol-5-ylsulphanyl)-propionic acid methyl ester

被引：8

作者：

Al-Soud, YA

Al-Masoudi, NA

机构：

[1] Univ Al al Bayt, Coll Sci, Dept Chem, Al Mafraq, Jordan

[2] Univ Konstanz, Fachbereich Chem, D-7750 Constance, Germany

来源：

SYNTHETIC COMMUNICATIONS | 2005年 / 35卷 / 17期

关键词：

cyclization; 4-nitroimidazole; nucleophilic substitution; meso-product;

D O I：

10.1080/00397910500184735

中图分类号：

O62 [有机化学];

学科分类号：

070303 [有机化学]; 081704 [应用化学];

摘要：

Nucleophilic substitution of the 5-bromo group in 1 by methyl 3-mercaptopropionate gave the 5-alkyl-mercapto derivative 2. Reduction of 2 with H-2/Pd led to the amine 3, meanwhile reduction with Fe/HOAc afforded the 5-acetamido derivative 4 and not the cyclized derivative 1,3,8-triaza-azulen-7-one 6, as expected. Treatment of 3 with NaOMe/MeOH furnished the racemic mixture 5a and 5b via an unexpected reactivity.

引用

页码：2259 / 2264

页数：6

共 12 条

[1]

ALMASOUDI NA, 2005, UNPUB CHEM BIODIVER

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SYNTHESIS AND CA(2+)ANTAGONISTIC ACTIVITY OF A THIENO-KT-362 ANALOG [J].