DBU-catalyzed substitution-controlled synthesis of oxa[3.3.1] bridged ring and naphthylamine derivatives

Shiyu Xu; Zhihui Sun; Pengyutian Liu; Yuanlin Wei; Fan Sun; Man Zhao; Ying Wang; Ming Zhang; Guofeng Li; Hong Liang

doi:10.1039/D4QO00012A

DBU-catalyzed substitution-controlled synthesis of oxa[3.3.1] bridged ring and naphthylamine derivatives†

Shiyu Xu,^a Zhihui Sun,^a Pengyutian Liu,^b Yuanlin Wei,^a Fan Sun,^a Man Zhao,^b Ying Wang,^b Ming Zhang,*^b Guofeng Li

*^b and Hong Liang

*^a

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* Corresponding authors

^a Guangdong Key Laboratory of Chiral Molecule and Drug Discovery, School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou, Guangdong 510006, China
E-mail: hongliang@sysu.edu.cn

^b School of Pharmacy, Shenzhen University Medical School, Shenzhen University, Shenzhen, China
E-mail: liguofeng@szu.edu.cn, zhangm383@mail.sysu.edu.cn

Abstract

A switchable cascade cyclization reaction of ortho-alkynyl arylketones with amines has been developed. The different reaction pathways are controlled by the substituent on the α-carbon of in situ generated ortho-alkynyl arylaldimines. Under the catalysis of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), oxa[3.3.1] bridged ring compounds and 1-naphthylamine derivatives are obtained with high yields and excellent regioselectivities. This transformation is metal-free, and has mild reaction conditions, high atom utilization and strong substrate applicability.

Organic Chemistry Frontiers

DBU-catalyzed substitution-controlled synthesis of oxa[3.3.1] bridged ring and naphthylamine derivatives†

Abstract

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DBU-catalyzed substitution-controlled synthesis of oxa[3.3.1] bridged ring and naphthylamine derivatives

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