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1

Tetrahedron

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Three-component one-pot synthesis of aldehyde/ketone, thiosemicarbazide and

c hlorinate

d β- keto ester

Given-name Surname 1a , Given-name Surname 2a, * and Given-name Surname 3b

Xinjiang University, Urumqi 830046, PR China

———

* Corresponding author. Tel.: +0-000-000-0000; fax: +0-000-000-0000; e-mail: author@

1.Introduction

Heterocyclic compound are widespread in nature with many

different kinds and large number, such as some alkaloids,

vitamins, antibiotics, etc. Due to the differences among the

species and the number of heteroatoms, ring members and the

ring number in heterocyclic drug molecules, which have been

classified into many different categories, such as pyridine,

quinoline, phenothiazine, benzodiazepines, furan, pyrazole

ketones, pyrimidine, thiazole, etc. Among them, five-member

heterocyclic compounds are the most important compounds

associated with biology.

Thiazole derivatives is a kind of important five-member

heterocyclic derivatives containing nitrogen, sulfur atom and a

thiazole functional group, and has aromaticity. The value of

biological activity, pharmacological activity and optical

properties of thiazole compounds have been reported widely in

literature, so this kind of compounds are with high application

value and research value. It has a wide range of biological

activity including antibacterial[1], antifungal[2], anti-

inflammatory [3], antihypertensive[4], anti-HIV[5], anti-tumor

[6 ~ 9], etc. Thiazole is used to prepare biocides, fungicides,

medicine and dye [10], and also plays an important role in

regulating humans and other biological metabolism process. The

research of new thiazole compounds has become one of the

important areas of new drug research.

Multi-component reaction means that three or more

compounds react in a container to form new compounds which

contain the main structure fragments of all components. Due to

simple operation, good selectivity, saving time, reducing the

purification steps, improving the reaction yield and environment

friendly and so on, most multi-component reactions have

become an important method and means in organic synthesis.

Our group aimed at synthesizing thiazole compounds and

prepared multi-substituted thiazole compounds by one-pot multi-

component synthetic method, and determined the structure of the

target compounds by 1H NMR, IR and MS.In this paper, a series

of thiazole compounds were synthesized successfully catalyzed

by anhydrous sodium acetate in ethanol solvent. Ethanol, as a

common solvent, its solubility and volatility is relatively good,

non-toxic, miscible with water, easy post-processing, and its

production process is the fermentation process whose price is

low and raw material can be waste products from crops such as

straw without toxic and harmful by-products in production

process. Therefore, ethanol is an important solvent in accordance

with standard of modern green chemistry. Anhydrous sodium

acetate as catalyst in the reaction has high catalytic ability and is

green and efficient, and can greatly improve yields. In addition,

it can also be used as a phase transfer catalyst, applying to the

interface reaction which is with fast reaction rate, easy operation,

without too much by-products and have certain innovation. ART I CLE I NFO AB ST R ACT

Article history:

Received

Received in revised form

Accepted

Available online

A series of novel thiazole compounds are synthesized with one-pot three-component reaction of

aldehyde/ketone, thiosemicarbazide and chlorinated β-keto ester catalyzed by anhydrous sodium

acetate . The reaction produced has excellent yields in EtOH solvent. The structures of products

are confirmed by 1H NMR, IR and MS. Also, the synthetic method and reaction mechanism are

discussed.

2009 Elsevier Ltd. All rights reserved. Keywords:

chlorinated β-keto ester

thiazole/hydrazone compounds

three-component reaction

one-pot synthesis