In Situ Activation of Azaarenes and Terminal Alkynes to Construct Bridged Polycyclic Compounds Containing Isoquinolinones

Jianyi Shi; Zhongzhi Zhu; Zhendong Yang; Yuqun Lin; Tong Yu; Mingli Zhong; Tsz Woon Benedict Lo; Xiuwen Chen; Tiangang Luan

doi:10.1021/acs.orglett.4c00006

In Situ Activation of Azaarenes and Terminal Alkynes to Construct Bridged Polycyclic Compounds Containing Isoquinolinones

Jianyi Shi
, Zhongzhi Zhu
, Zhendong Yang
, Yuqun Lin
, Tong Yu
, Mingli Zhong
, Tsz Woon Benedict Lo
, Xiuwen Chen
, Tiangang Luan

The Hong Kong Polytechnic University

Research output: Journal article publication › Journal article › Academic research › peer-review

8 Citations (Scopus)

Abstract

A copper-catalyzed [4+2] cyclization reaction of isoquinolines and alkynes is developed for the one-step construction of isoquinolinone derivatives with multisubstituted bridging rings. The unique feature of this three-component tandem cyclization reaction is the functionalization of the C1, N2, C3, and C4 positions of 3-haloisoquinolines via the construction of new C-N, C═O, and C-C bonds. This dearomatization strategy for the synthesis of structurally complex isoquinolinone-bridged cyclic compounds offers good chemoselectivity, broad functional group compatibility, greenness, and high step economy.

Original language	English
Pages (from-to)	2002-2006
Number of pages	5
Journal	Organic Letters
Volume	26
Issue number	10
DOIs	https://doi.org/10.1021/acs.orglett.4c00006
Publication status	Published - 23 Feb 2024

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

More information

10.1021/acs.orglett.4c00006

http://hdl.handle.net/10397/108920

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title = "In Situ Activation of Azaarenes and Terminal Alkynes to Construct Bridged Polycyclic Compounds Containing Isoquinolinones",

abstract = "A copper-catalyzed [4+2] cyclization reaction of isoquinolines and alkynes is developed for the one-step construction of isoquinolinone derivatives with multisubstituted bridging rings. The unique feature of this three-component tandem cyclization reaction is the functionalization of the C1, N2, C3, and C4 positions of 3-haloisoquinolines via the construction of new C-N, C═O, and C-C bonds. This dearomatization strategy for the synthesis of structurally complex isoquinolinone-bridged cyclic compounds offers good chemoselectivity, broad functional group compatibility, greenness, and high step economy.",

author = "Jianyi Shi and Zhongzhi Zhu and Zhendong Yang and Yuqun Lin and Tong Yu and Mingli Zhong and Lo, \{Tsz Woon Benedict\} and Xiuwen Chen and Tiangang Luan",

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T1 - In Situ Activation of Azaarenes and Terminal Alkynes to Construct Bridged Polycyclic Compounds Containing Isoquinolinones

AU - Shi, Jianyi

AU - Zhu, Zhongzhi

AU - Yang, Zhendong

AU - Lin, Yuqun

AU - Yu, Tong

AU - Zhong, Mingli

AU - Lo, Tsz Woon Benedict

AU - Chen, Xiuwen

AU - Luan, Tiangang

PY - 2024/2/23

Y1 - 2024/2/23

N2 - A copper-catalyzed [4+2] cyclization reaction of isoquinolines and alkynes is developed for the one-step construction of isoquinolinone derivatives with multisubstituted bridging rings. The unique feature of this three-component tandem cyclization reaction is the functionalization of the C1, N2, C3, and C4 positions of 3-haloisoquinolines via the construction of new C-N, C═O, and C-C bonds. This dearomatization strategy for the synthesis of structurally complex isoquinolinone-bridged cyclic compounds offers good chemoselectivity, broad functional group compatibility, greenness, and high step economy.

AB - A copper-catalyzed [4+2] cyclization reaction of isoquinolines and alkynes is developed for the one-step construction of isoquinolinone derivatives with multisubstituted bridging rings. The unique feature of this three-component tandem cyclization reaction is the functionalization of the C1, N2, C3, and C4 positions of 3-haloisoquinolines via the construction of new C-N, C═O, and C-C bonds. This dearomatization strategy for the synthesis of structurally complex isoquinolinone-bridged cyclic compounds offers good chemoselectivity, broad functional group compatibility, greenness, and high step economy.

UR - https://www.scopus.com/pages/publications/85186199509

U2 - 10.1021/acs.orglett.4c00006

DO - 10.1021/acs.orglett.4c00006

M3 - Journal article

C2 - 38394378

AN - SCOPUS:85186199509

SN - 1523-7060

VL - 26

SP - 2002

EP - 2006

JO - Organic Letters

JF - Organic Letters

IS - 10

ER -

In Situ Activation of Azaarenes and Terminal Alkynes to Construct Bridged Polycyclic Compounds Containing Isoquinolinones

Abstract

ASJC Scopus subject areas

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