Combining photo-redox and enzyme catalysis for the synthesis of 4H-pyrimido[2,1-b] benzothiazole derivatives in one pot.

Bioorg Chem

Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, PR China. Electronic address:

Published: February 2021

A novel strategy combining visible-light and enzyme catalysis in one pot for the synthesis of 4H-pyrimido[2,1-b] benzothiazole derivatives from alcohols is described for the first time. Fourteen 4H-pyrimido[2,1-b] benzothiazole derivatives were prepared with yields of up to 98% under mild reaction conditions by a simple operation. The photoorgano catalyst rose Bengal (rB) was employed to oxyfunctionalise alcohols to aldehydes. Compared with aldehydes, alcohols with more stable properties and lower cost, thus we used photocatalysis to oxidize alcohols into aldehydes. Next, the enzyme was used to further catalyze the reaction of Biginelli to produce the target product of 4H-pyrimidine [2,1-b] benzothiazole. Experimental results show that this method provides a more efficient and eco-friendly strategy for the synthesis of 4H-pyrimido[2,1-b] benzothiazole derivatives.

Download full-text PDF

Source
http://dx.doi.org/10.1016/j.bioorg.2020.104534DOI Listing

Publication Analysis

Top Keywords

4h-pyrimido[21-b] benzothiazole
16
benzothiazole derivatives
16
synthesis 4h-pyrimido[21-b]
12
enzyme catalysis
8
alcohols aldehydes
8
benzothiazole
5
combining photo-redox
4
photo-redox enzyme
4
catalysis synthesis
4
4h-pyrimido[21-b]
4

Similar Publications

Background: The magnetic nano-catalysts improve the contact between substrates and catalyst considerably and simple isolation of catalyst from reaction mixture. In this study, FeO@nano-almondshell@OSi(CH)/2-(1-piperazinyl)ethylamine/Cu(II) abbreviated (FNAOSiPPEA/Cu(II)), was prepared, characterized and applied for the synthesis of 4H-pyrimido[2,1-b]benzothiazole.

Results: FNAOSiPPEA/Cu(II) as a bio-based nano-catalyst was prepared from the complexation of copper on 2-(1-piperazinyl)ethylamine, which was immobilized on FeO@nano-almondshell@OSi(CH) section.

View Article and Find Full Text PDF

Combining photo-redox and enzyme catalysis for the synthesis of 4H-pyrimido[2,1-b] benzothiazole derivatives in one pot.

Bioorg Chem

February 2021

Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, PR China. Electronic address:

A novel strategy combining visible-light and enzyme catalysis in one pot for the synthesis of 4H-pyrimido[2,1-b] benzothiazole derivatives from alcohols is described for the first time. Fourteen 4H-pyrimido[2,1-b] benzothiazole derivatives were prepared with yields of up to 98% under mild reaction conditions by a simple operation. The photoorgano catalyst rose Bengal (rB) was employed to oxyfunctionalise alcohols to aldehydes.

View Article and Find Full Text PDF

Enzyme-catalysed one-pot synthesis of 4H-pyrimido[2,1-b] benzothiazoles and their application in subcellular imaging.

J Biotechnol

December 2020

Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu, 610064, PR China. Electronic address:

Enzymes, which provide more efficient and eco-friendly strategies for various functional molecules' construction than traditional chemo-catalysts, were utilized for the synthesis of 4H-pyrimido[2,1-b] benzothiazole derivatives. Reported herein is a trypsin-catalysed three- component Biginelli reaction of aldehyde, β-ketoester and 2-amino benzothiazole in one pot, affording a streamlined pathway to diverse ring-fused pyrimidines. In addition to using commercially available aromatic aldehydes as substrates, acetaldehyde, the chemical liquid with rather low boiling point and difficult to handle above room temperature, is utilized to further extend the range of substrates.

View Article and Find Full Text PDF

Aggregation-Induced Emission Probes for Specific Turn-On Quantification of Bovine Serum Albumin.

ACS Appl Bio Mater

August 2020

Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, P. R. China.

A series of aggregation-induced emission (AIE) fluorescence probes, coined 4H-pyrimido[2,1-]benzothiazole derivatives, has been synthesized by Biginelli reactions. Utilizing spectroscopic techniques, their photophysical properties have been comprehensively investigated in working environment both and . Density functional theory (DFT) calculations were performed to better understand the mechanism of these probes.

View Article and Find Full Text PDF

A straight forward and highly efficient one-pot annulation of 2-aminobenzothiazole, (E)-N-methyl-1-(methylthio)-2-nitroethenamine, and aldehydes in the presence of FeF is described. Diverse functionalized N-methyl-3-nitro-4H-pyrimido [2, 1-b] [1, 3] benzothiazole-2-amine derivatives were obtained with excellent yields under neat conditions. The one-pot annulation was shown to be valid for the synthesis of highly functionalized derivatives of N-methyl-3-nitro-4H-pyrimido [2, 1-b] [1, 3] benzothiazole-2-amine from readily accessible substrates.

View Article and Find Full Text PDF

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!