4.7 Article

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

Journal

BIOORGANIC CHEMISTRY
Volume 107, Issue -, Pages -

Publisher

ACADEMIC PRESS INC ELSEVIER SCIENCE
DOI: 10.1016/j.bioorg.2020.104534

Keywords

Photocatalysis; Biocatalysis; One pot; Cascades; 4H-pyrimido[2,1-b]benzothiazoles

Funding

  1. National Key R&D Program of China [2018YFA0901600]
  2. Comprehensive Training Platform of Specialized Laboratory, College of Chemistry, Sichuan University

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A novel strategy combining visible-light and enzyme catalysis was successfully applied for the synthesis of 4H-pyrimido [2,1-b] benzothiazole derivatives in one pot, achieving high yields and easy operation. By utilizing a photoorgano catalyst and enzyme, alcohols were efficiently oxidized into aldehydes, leading to a more efficient and eco-friendly approach for the synthesis of 4H-pyrimido [2,1-b] benzothiazole derivatives.
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.

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