Lewis Acid-Catalyzed C(sp3)–C(sp3) Bond Forming Cyclization Reactions for the Synthesis of Tetrahydroprotoberberine Derivatives

Jianjun Li; Cong Qin; Yang Yu; Huaqiang Fan; Yiwei Fu; Hao Li; Wei Wang

doi:10.1002/adsc.201601423

Lewis Acid-Catalyzed C(sp³)–C(sp³) Bond Forming Cyclization Reactions for the Synthesis of Tetrahydroprotoberberine Derivatives

Jianjun Li, Cong Qin, Yang Yu, Huaqiang Fan, Yiwei Fu, Hao Li, Wei Wang

Research output: Contribution to journal › Article › peer-review

22 Scopus citations

Abstract

An efficient Lewis acid-catalyzed C(sp³)–C(sp³) bond forming annulation reaction has been developed. This strategy serves as a new method for the facile synthesis of tetrahydro-5H-isoquinolino[2,1-g][1,6]naphthyridine derivatives. A wide range of 2-methylquinoline-3-carbaldehydes and 1,2,3,4-tetrahydroisoquinolines can be applied for this process to afford structurally diverse tetrahydroprotoberberine derivatives in excellent yields. (Figure presented.).

Original language	English (US)
Pages (from-to)	2191-2195
Number of pages	5
Journal	Advanced Synthesis and Catalysis
Volume	359
Issue number	13
DOIs	https://doi.org/10.1002/adsc.201601423
State	Published - Jul 3 2017
Externally published	Yes

Keywords

C(sp)–C(sp) bond formation
Lewis acid catalysis
annulation
azaarene activation
tetrahydroprotoberberine derivatives

ASJC Scopus subject areas

Catalysis
Organic Chemistry

Access to Document

10.1002/adsc.201601423

Cite this

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title = "Lewis Acid-Catalyzed C(sp3)–C(sp3) Bond Forming Cyclization Reactions for the Synthesis of Tetrahydroprotoberberine Derivatives",

abstract = "An efficient Lewis acid-catalyzed C(sp3)–C(sp3) bond forming annulation reaction has been developed. This strategy serves as a new method for the facile synthesis of tetrahydro-5H-isoquinolino[2,1-g][1,6]naphthyridine derivatives. A wide range of 2-methylquinoline-3-carbaldehydes and 1,2,3,4-tetrahydroisoquinolines can be applied for this process to afford structurally diverse tetrahydroprotoberberine derivatives in excellent yields. (Figure presented.).",

keywords = "C(sp)–C(sp) bond formation, Lewis acid catalysis, annulation, azaarene activation, tetrahydroprotoberberine derivatives",

author = "Jianjun Li and Cong Qin and Yang Yu and Huaqiang Fan and Yiwei Fu and Hao Li and Wei Wang",

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T1 - Lewis Acid-Catalyzed C(sp3)–C(sp3) Bond Forming Cyclization Reactions for the Synthesis of Tetrahydroprotoberberine Derivatives

AU - Li, Jianjun

AU - Qin, Cong

AU - Yu, Yang

AU - Fan, Huaqiang

AU - Fu, Yiwei

AU - Li, Hao

AU - Wang, Wei

PY - 2017/7/3

Y1 - 2017/7/3

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AB - An efficient Lewis acid-catalyzed C(sp3)–C(sp3) bond forming annulation reaction has been developed. This strategy serves as a new method for the facile synthesis of tetrahydro-5H-isoquinolino[2,1-g][1,6]naphthyridine derivatives. A wide range of 2-methylquinoline-3-carbaldehydes and 1,2,3,4-tetrahydroisoquinolines can be applied for this process to afford structurally diverse tetrahydroprotoberberine derivatives in excellent yields. (Figure presented.).

KW - C(sp)–C(sp) bond formation

KW - Lewis acid catalysis

KW - annulation

KW - azaarene activation

KW - tetrahydroprotoberberine derivatives

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