Enantioselective synthesis of functionalized 1,4-dihydropyrazolo-[4',3':5,6]pyrano[2,3- b]quinolines through ferrocenyl-phosphine-catalyzed annulation of modified MBH carbonates and pyrazolones

Xiao Xiao; Bingxuan Shao; Jingyi Li; Zehui Yang; Yin-Jie Lu; Fei Ling; Weihui Zhong

doi:10.1039/d1cc00989c

Enantioselective synthesis of functionalized 1,4-dihydropyrazolo-[4',3':5,6]pyrano[2,3- b]quinolines through ferrocenyl-phosphine-catalyzed annulation of modified MBH carbonates and pyrazolones

Chem Commun (Camb). 2021 May 11;57(38):4690-4693. doi: 10.1039/d1cc00989c.

Authors

Xiao Xiao¹, Bingxuan Shao², Jingyi Li², Zehui Yang², Yin-Jie Lu³, Fei Ling², Weihui Zhong²

Affiliations

¹ Institute of Pharmaceutical Science and Technology, Zhejiang University of Technology, Hangzhou 310014, People's Republic of China and College of Pharmaceutical Sciences, Zhejiang University of Technology, Hangzhou 310014, People's Republic of China.
² College of Pharmaceutical Sciences, Zhejiang University of Technology, Hangzhou 310014, People's Republic of China.
³ Institute of Pharmaceutical Science and Technology, Zhejiang University of Technology, Hangzhou 310014, People's Republic of China.

PMID: 33977995
DOI: 10.1039/d1cc00989c

Abstract

An enantioselective synthesis of highly functionalized 1,4-dihydropyrazolo[4',3':5,6]pyrano[2,3-b]quinolines from modified MBH carbonates and pyrazolones via a chiral phosphine-mediated alkylation/annulation sequence has been realized. The chiral dihydropyrano[2,3-c]pyrazoles bearing bio-active condensed heterocycles were facilely formed in good chemical yields and with high to excellent enantioselectivity by utilizing low catalyst loading.