Abstract
A novel chemoenzymatic one-pot multicomponent synthesis of thiazole derivatives was developed. A series of thiazole derivatives were synthesized with high yields up to 94% under mild enzyme-catalyzed conditions. The blank and control experiments reveal that trypsin from porcine pancreas (PPT) displayed great catalytic activity to promote this reaction and showed a wide tolerance range towards different substrate amines. This trypsin-catalyzed multicomponent conversion method provides a novel strategy to synthesize thiazole derivatives and expands the application of enzymes in organic synthesis.
Highlights
Thiazoles and their derivatives are an important class of heterocyclic compounds which possess broad biological activities, such as antimicrobial [1], antipyretic [2], antiparasitic [3], antihistaminic [4], and antiviral properties [5]
Thiazoles have traditionally been synthesized by the Hantzsch synthesis [7,8], which suffers from some disadvantages such as long reaction times, low yields and harsh reaction conditions
We have been interested in the study of chemoenzymatic organic reactions and especially the enzymatic synthesis of heterocyclic compounds [11,12]
Summary
Thiazoles and their derivatives are an important class of heterocyclic compounds which possess broad biological activities, such as antimicrobial [1], antipyretic [2], antiparasitic [3], antihistaminic [4], and antiviral properties [5]. Thiazoles have traditionally been synthesized by the Hantzsch synthesis [7,8], which suffers from some disadvantages such as long reaction times, low yields and harsh reaction conditions. There are some reports using microwave irradiation in the Hantzsch reaction to overcome these disadvantages [9,10], the development of novel methods for the preparation of thiazoles derivatives is still in demand. We have been interested in the study of chemoenzymatic organic reactions and especially the enzymatic synthesis of heterocyclic compounds [11,12]. As a continuation of our work studying chemoenzymatic organic reactions, we report a novel strategy for the high yielding chemoenzymatic one-pot multicomponent synthesis under mild conditions of thiazole derivatives from secondary amines, benzoyl isothiocyanate, and dialkyl acetylenedicarboxylates as starting materials
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