Diversity-oriented synthesis of benzofuro[3,2- b]pyridine derivatives from aurone-derived α,β-unsaturated imines and activated terminal alkynes

Bin Cheng; Hui Li; Xuecheng Zhu; Xinping Zhang; Yixuan He; Haiyan Sun; Taimin Wang; Hongbin Zhai

doi:10.1039/d1cc02477a

Diversity-oriented synthesis of benzofuro[3,2- b]pyridine derivatives from aurone-derived α,β-unsaturated imines and activated terminal alkynes

Chem Commun (Camb). 2021 Aug 3;57(62):7701-7704. doi: 10.1039/d1cc02477a.

Authors

Bin Cheng¹, Hui Li¹, Xuecheng Zhu¹, Xinping Zhang¹, Yixuan He¹, Haiyan Sun², Taimin Wang², Hongbin Zhai³

Affiliations

¹ Institute of Marine Biomedicine/Hoffmann Institute of Advanced Materials, Shenzhen Polytechnic, Shenzhen 518055, China. chengbin@szpt.edu.cn wangtm@szpt.edu.cn and State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, China.
² Institute of Marine Biomedicine/Hoffmann Institute of Advanced Materials, Shenzhen Polytechnic, Shenzhen 518055, China. chengbin@szpt.edu.cn wangtm@szpt.edu.cn.
³ Institute of Marine Biomedicine/Hoffmann Institute of Advanced Materials, Shenzhen Polytechnic, Shenzhen 518055, China. chengbin@szpt.edu.cn wangtm@szpt.edu.cn and State Key Laboratory of Chemical Oncogenomics, Shenzhen Engineering Laboratory of Nano Drug Slow-Release, Peking University Shenzhen Graduate School, Shenzhen 518055, China. zhaihb@pkusz.edu.cn.

PMID: 34259255
DOI: 10.1039/d1cc02477a

Abstract

An efficient annulation reaction of aurone-derived α,β-unsaturated imines and activated terminal alkynes mediated by triethylamine is described, which enables the facile synthesis of 1,4-dihydrobenzofuro[3,2-b]pyridines in high yields. When the nucleophile of triethylamine was replaced with triphenylphosphine, another class of 1,4-dihydrobenzofuro[3,2-b]pyridines tethered with an additional acrylate motif were obtained instead. These two types of 1,4-dihydrobenzofuro[3,2-b]pyridines could be aromatized in the presence of DBU to afford benzofuro[3,2-b]pyridines, which could also be accessed via a one-pot procedure.