An efficient method for 3,4-dihydroisoquinolinium ion formation, leading to a facile introduction of nucleophiles

Makoto Shimizu; Takato Kawamura; Shinya Fukumoto; Isao Mizota; Yusong Zhu

doi:10.1002/jhet.4211

An efficient method for 3,4-dihydroisoquinolinium ion formation, leading to a facile introduction of nucleophiles

Makoto Shimizu, Takato Kawamura, Shinya Fukumoto, Isao Mizota, Yusong Zhu

School of energy science and engineering

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

Abstract

The ketene silyl acetal derived from ethyl 2-benzyltetrahydroisoquinoline-1-carboxylate undergoes a rapid oxidation reaction with N-bromosuccinimide to form 3,4-dihydroisoquinolinium ion, which reacts with Grignard reagents to give 1,1-disubstituted tetrahydroisoquinolines in good yields.

Original language	English
Pages (from-to)	751-756
Number of pages	6
Journal	Journal of Heterocyclic Chemistry
Volume	58
Issue number	3
DOIs	https://doi.org/10.1002/jhet.4211
State	Published - Mar 2021

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10.1002/jhet.4211

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title = "An efficient method for 3,4-dihydroisoquinolinium ion formation, leading to a facile introduction of nucleophiles",

abstract = "The ketene silyl acetal derived from ethyl 2-benzyltetrahydroisoquinoline-1-carboxylate undergoes a rapid oxidation reaction with N-bromosuccinimide to form 3,4-dihydroisoquinolinium ion, which reacts with Grignard reagents to give 1,1-disubstituted tetrahydroisoquinolines in good yields.",

author = "Makoto Shimizu and Takato Kawamura and Shinya Fukumoto and Isao Mizota and Yusong Zhu",

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AU - Shimizu, Makoto

AU - Kawamura, Takato

AU - Fukumoto, Shinya

AU - Mizota, Isao

AU - Zhu, Yusong

PY - 2021/3

Y1 - 2021/3

N2 - The ketene silyl acetal derived from ethyl 2-benzyltetrahydroisoquinoline-1-carboxylate undergoes a rapid oxidation reaction with N-bromosuccinimide to form 3,4-dihydroisoquinolinium ion, which reacts with Grignard reagents to give 1,1-disubstituted tetrahydroisoquinolines in good yields.

AB - The ketene silyl acetal derived from ethyl 2-benzyltetrahydroisoquinoline-1-carboxylate undergoes a rapid oxidation reaction with N-bromosuccinimide to form 3,4-dihydroisoquinolinium ion, which reacts with Grignard reagents to give 1,1-disubstituted tetrahydroisoquinolines in good yields.

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M3 - 文章

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SN - 0022-152X

VL - 58

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EP - 756

JO - Journal of Heterocyclic Chemistry

JF - Journal of Heterocyclic Chemistry

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ER -

An efficient method for 3,4-dihydroisoquinolinium ion formation, leading to a facile introduction of nucleophiles

Abstract

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