One-pot cascade synthesis of benzopyrans and dihydropyrano[c]chromenes catalyzed by lipase TLIM

Yajie Fu; Zeping Lu; Xiaolong Ma; Ke Fang; Xinyi He; Huajin Xu; Yi Hu

doi:10.1016/j.bioorg.2020.103888

One-pot cascade synthesis of benzopyrans and dihydropyrano[c]chromenes catalyzed by lipase TLIM

Bioorg Chem. 2020 Jun:99:103888. doi: 10.1016/j.bioorg.2020.103888. Epub 2020 Apr 29.

Authors

Yajie Fu¹, Zeping Lu¹, Xiaolong Ma¹, Ke Fang¹, Xinyi He¹, Huajin Xu¹, Yi Hu²

Affiliations

¹ State Key Laboratory of Materials-Oriented Chemical Engineering, School of Pharmaceutical Sciences, Nanjing Tech University, Nanjing 210009, China.
² State Key Laboratory of Materials-Oriented Chemical Engineering, School of Pharmaceutical Sciences, Nanjing Tech University, Nanjing 210009, China. Electronic address: huyi@njtech.edu.cn.

PMID: 32388204
DOI: 10.1016/j.bioorg.2020.103888

Abstract

Lipase TLIM was reported to be an efficient, commercially available and reusable catalyst for the Knoevenagel-Michael cascade reactions of aldehydes, malononitrile/ethyl cyanoacetate and 4-hydroxycoumarin/1, 3-cyclohexanedione/dimedone in aqueous DMSO. This methodology presents many superiorities such as simple procedure, mild reaction conditions, commercially available and reusable catalyst, high substrate applicability, the ability to be scaled up, and good to excellent yields.

Keywords: Benzopyrans; Cascade reactions; Chromene; Enzymatic synthesis; Lipase.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Benzopyrans / chemistry
Benzopyrans / metabolism*
Biocatalysis
Lipase / metabolism*
Molecular Structure
Rhizomucor / enzymology

Substances

Benzopyrans
Lipozyme
Lipase

Supplementary concepts

Rhizomucor miehei