Synthesis of 1H-isoindoliums by electrophile-mediated cascade cyclization/iodination of propargylamine-based 1,6-diynes

Jian Fang Cui; Qiong Yu; O. Wa-Yi; Li Wu Huang; Bin Yang; Man Kin Wong

doi:10.1039/d2ob00316c

Synthesis of 1H-isoindoliums by electrophile-mediated cascade cyclization/iodination of propargylamine-based 1,6-diynes

Jian Fang Cui, Qiong Yu, O. Wa-Yi, Li Wu Huang, Bin Yang, Man Kin Wong

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

3 Citations (Scopus)

Abstract

A highly regio- and chemoselective synthesis of 1H-isoindoliums through a facile and novel cascade cyclization reaction of propargylamine-based 1,6-diynes under mild conditions has been developed. Different functional groups were compatible under the optimized reaction conditions, giving the corresponding products in up to 94% yields. Upon treatment with a base, the alkyne moiety of 1H-isoindoliums could be further transformed to allenes in excellent yields.

Original language	English
Pages (from-to)	3755-3762
Number of pages	8
Journal	Organic and Biomolecular Chemistry
Volume	20
Issue number	18
DOIs	https://doi.org/10.1039/d2ob00316c
Publication status	Published - 7 Apr 2022

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

More information

10.1039/d2ob00316c

http://hdl.handle.net/10397/95775

Cite this

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title = "Synthesis of 1H-isoindoliums by electrophile-mediated cascade cyclization/iodination of propargylamine-based 1,6-diynes",

abstract = "A highly regio- and chemoselective synthesis of 1H-isoindoliums through a facile and novel cascade cyclization reaction of propargylamine-based 1,6-diynes under mild conditions has been developed. Different functional groups were compatible under the optimized reaction conditions, giving the corresponding products in up to 94% yields. Upon treatment with a base, the alkyne moiety of 1H-isoindoliums could be further transformed to allenes in excellent yields.",

author = "Cui, {Jian Fang} and Qiong Yu and O. Wa-Yi and Huang, {Li Wu} and Bin Yang and Wong, {Man Kin}",

note = "Funding Information: We are grateful for the financial support from Hong Kong Research Grants Council (PolyU 153001/17P), Shenzhen Science and Technology Innovation Commission (JCYJ20170818104257975), the State Key Laboratory of Chemical Biology and Drug Discovery, and the Hong Kong Polytechnic University (P0034752: ZVST). Publisher Copyright: {\textcopyright} 2022 The Royal Society of Chemistry",

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AU - Cui, Jian Fang

AU - Yu, Qiong

AU - Wa-Yi, O.

AU - Huang, Li Wu

AU - Yang, Bin

AU - Wong, Man Kin

N1 - Funding Information: We are grateful for the financial support from Hong Kong Research Grants Council (PolyU 153001/17P), Shenzhen Science and Technology Innovation Commission (JCYJ20170818104257975), the State Key Laboratory of Chemical Biology and Drug Discovery, and the Hong Kong Polytechnic University (P0034752: ZVST). Publisher Copyright: © 2022 The Royal Society of Chemistry

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N2 - A highly regio- and chemoselective synthesis of 1H-isoindoliums through a facile and novel cascade cyclization reaction of propargylamine-based 1,6-diynes under mild conditions has been developed. Different functional groups were compatible under the optimized reaction conditions, giving the corresponding products in up to 94% yields. Upon treatment with a base, the alkyne moiety of 1H-isoindoliums could be further transformed to allenes in excellent yields.

AB - A highly regio- and chemoselective synthesis of 1H-isoindoliums through a facile and novel cascade cyclization reaction of propargylamine-based 1,6-diynes under mild conditions has been developed. Different functional groups were compatible under the optimized reaction conditions, giving the corresponding products in up to 94% yields. Upon treatment with a base, the alkyne moiety of 1H-isoindoliums could be further transformed to allenes in excellent yields.

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DO - 10.1039/d2ob00316c

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Synthesis of 1H-isoindoliums by electrophile-mediated cascade cyclization/iodination of propargylamine-based 1,6-diynes

Abstract

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