Gold(I)-catalyzed 10-endo-dig-selective cycloisomerization of N-(2-anilinobenzyl)propargylamines

Mamoru Ito; Daisuke Inoue; Asahi Takaki; Kyalo Stephen Kanyiva; Takanori Shibata

doi:10.3987/COM-19-S(F)13

Gold(I)-catalyzed 10-endo-dig-selective cycloisomerization of N-(2-anilinobenzyl)propargylamines

Mamoru Ito, Daisuke Inoue, Asahi Takaki, Kyalo Stephen Kanyiva, Takanori Shibata^*

^*Corresponding author for this work

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

2 Citations (Scopus)

Abstract

– The cationic gold(I)-catalyzed 10-endo-dig-selective cycloisomerization of N-(2-anilinobenzyl)propargylamine derivatives was developed. The reaction proceeded smoothly under mild conditions to give dibenzodiazecines. The catalytic construction of an entropically and enthalpically disfavored ten-membered ring was achieved by using a highly nucleophilic 3,5-dimethoxyanilino group as a reaction site.

Original language	English
Pages (from-to)	195-208
Number of pages	14
Journal	Heterocycles
Volume	101
Issue number	1
DOIs	https://doi.org/10.3987/COM-19-S(F)13
Publication status	Published - 2020

ASJC Scopus subject areas

Analytical Chemistry
Pharmacology
Organic Chemistry

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title = "Gold(I)-catalyzed 10-endo-dig-selective cycloisomerization of N-(2-anilinobenzyl)propargylamines",

abstract = "– The cationic gold(I)-catalyzed 10-endo-dig-selective cycloisomerization of N-(2-anilinobenzyl)propargylamine derivatives was developed. The reaction proceeded smoothly under mild conditions to give dibenzodiazecines. The catalytic construction of an entropically and enthalpically disfavored ten-membered ring was achieved by using a highly nucleophilic 3,5-dimethoxyanilino group as a reaction site.",

author = "Mamoru Ito and Daisuke Inoue and Asahi Takaki and Kanyiva, {Kyalo Stephen} and Takanori Shibata",

note = "Funding Information: This work was supported by Mitsubishi Materials Corporation and Waseda University Joint Cooperation Publisher Copyright: {\textcopyright} 2020 The Japan Institute of Heterocyclic Chemistry",

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doi = "10.3987/COM-19-S(F)13",

language = "English",

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pages = "195--208",

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T1 - Gold(I)-catalyzed 10-endo-dig-selective cycloisomerization of N-(2-anilinobenzyl)propargylamines

AU - Ito, Mamoru

AU - Inoue, Daisuke

AU - Takaki, Asahi

AU - Kanyiva, Kyalo Stephen

AU - Shibata, Takanori

PY - 2020

Y1 - 2020

N2 - – The cationic gold(I)-catalyzed 10-endo-dig-selective cycloisomerization of N-(2-anilinobenzyl)propargylamine derivatives was developed. The reaction proceeded smoothly under mild conditions to give dibenzodiazecines. The catalytic construction of an entropically and enthalpically disfavored ten-membered ring was achieved by using a highly nucleophilic 3,5-dimethoxyanilino group as a reaction site.

AB - – The cationic gold(I)-catalyzed 10-endo-dig-selective cycloisomerization of N-(2-anilinobenzyl)propargylamine derivatives was developed. The reaction proceeded smoothly under mild conditions to give dibenzodiazecines. The catalytic construction of an entropically and enthalpically disfavored ten-membered ring was achieved by using a highly nucleophilic 3,5-dimethoxyanilino group as a reaction site.

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JO - Heterocycles

JF - Heterocycles

IS - 1

ER -

Gold(I)-catalyzed 10-endo-dig-selective cycloisomerization of N-(2-anilinobenzyl)propargylamines

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