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Stereoselective synthesis and characterization of monocyclic cis-β-lactams containing 5-methyl-1,3,4-thiadiazole-2-thiol moiety
Journal of Heterocyclic Chemistry ( IF 2.4 ) Pub Date : 2021-07-12 , DOI: 10.1002/jhet.4344
Vedeshwar N. Singh 1 , Sitaram Sharma 1
Affiliation  

This article describes the stereoselective synthesis of monocyclic cis-β-lactams. The 2-(4-chlorophenoxy)-acetic acid or 2-phenoxy-acetic acid with a carboxylic acid activator 2-ethoxy carbonyl DCPN generate ketene in situ, which reacts with imines derived from substituted tetralone carbaldehyde yielded monocyclic cis-β-lactams having 5-methyl-1,3,4-thiadiazole-2-thiol moiety through [2+2] cyclo-addition reaction (Staudinger reaction). All structures of cis-β-lactams were elucidated by a spectral technique like FT-IR, 1H and 13C NMR spectra, HRMS, and single X-ray crystallography. The cis configuration of the β-lactams was determined based on coupling constant (J) value using 1H NMR for hydrogens H-3 and H-4 of the β-lactams ring. This work presents the synthesis of β-lactams more simply with high yields. The products were simply purified by crystallization technique.

中文翻译:

含有 5-甲基-1,3,4-噻二唑-2-硫醇部分的单环顺式-β-内酰胺的立体选择性合成和表征

本文介绍的单环的立体选择性合成顺式β -内酰胺。与羧酸活化剂2-乙氧基羰基DCPN 2-(4-氯苯氧基) -乙酸或2-苯氧基-乙酸在原位产生烯酮其与亚胺起反应由取代的四氢萘酮衍生甲醛产生单环的顺式- β -内酰胺具有5-甲基-1,3,4-噻二唑-2-硫醇部分通过[2+2]环加成反应(施陶丁格反应)。顺式-β-内酰胺的所有结构均通过光谱技术(如 FT-IR、1 H 和13 C NMR 光谱、HRMS 和单 X 射线晶体学)阐明。该的β内酰胺的结构是基于耦合常数(确定Ĵ使用)值1 1 H NMR为氢H-3和β的H-4 -内酰胺环。这项工作提出了β的合成-内酰胺更简单,产量高。产物通过结晶技术简单纯化。
更新日期:2021-07-12
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