Regioselectivity of Pictet-Spengler cyclization: Synthesis of halotetrahydroisoquinolines

Su Dong Cho; Sang Yong Song; Eun Joo Hur; Ma Chen; Woo Hong Joo; J R Falck; Yong Jin Yoon; Dong Soo Shin

doi:10.1016/S0040-4039(01)01189-3

Regioselectivity of Pictet-Spengler cyclization: Synthesis of halotetrahydroisoquinolines

Su Dong Cho, Sang Yong Song, Eun Joo Hur, Ma Chen, Woo Hong Joo, J R Falck, Yong Jin Yoon, Dong Soo Shin

Biochemistry

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

16 Scopus citations

Abstract

The regioselectivity of the Pictet-Spengler cyclization for the synthesis of isoquinolines depends on the aryl substituent at C-2. The ratio of halotetrahydroisoquinoline 4 to isoquinoline 3 increases with increasing electrophilicity of the aromatic ring (H≪I<Br<Cl).

Original language	English (US)
Pages (from-to)	6251-6253
Number of pages	3
Journal	Tetrahedron Letters
Volume	42
Issue number	36
DOIs	https://doi.org/10.1016/S0040-4039(01)01189-3
State	Published - Sep 3 2001

Keywords

Condensation
Cyclization
Halotetrahydroisoquinoline
Pictet-Spengler

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(01)01189-3

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title = "Regioselectivity of Pictet-Spengler cyclization: Synthesis of halotetrahydroisoquinolines",

abstract = "The regioselectivity of the Pictet-Spengler cyclization for the synthesis of isoquinolines depends on the aryl substituent at C-2. The ratio of halotetrahydroisoquinoline 4 to isoquinoline 3 increases with increasing electrophilicity of the aromatic ring (H≪I<Br<Cl).",

keywords = "Condensation, Cyclization, Halotetrahydroisoquinoline, Pictet-Spengler",

author = "Cho, {Su Dong} and Song, {Sang Yong} and Hur, {Eun Joo} and Ma Chen and Joo, {Woo Hong} and Falck, {J R} and Yoon, {Yong Jin} and Shin, {Dong Soo}",

note = "Funding Information: The authors thank the Korea Research Foundation (KRF), the Institute of Basic Science of Changwon National University for a postdoctoral fellowship, the Robert A. Welch Foundation, and NIH (GM31278).",

year = "2001",

month = sep,

day = "3",

doi = "10.1016/S0040-4039(01)01189-3",

language = "English (US)",

volume = "42",

pages = "6251--6253",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

number = "36",

}

TY - JOUR

T1 - Regioselectivity of Pictet-Spengler cyclization

T2 - Synthesis of halotetrahydroisoquinolines

AU - Cho, Su Dong

AU - Song, Sang Yong

AU - Hur, Eun Joo

AU - Chen, Ma

AU - Joo, Woo Hong

AU - Falck, J R

AU - Yoon, Yong Jin

AU - Shin, Dong Soo

N1 - Funding Information: The authors thank the Korea Research Foundation (KRF), the Institute of Basic Science of Changwon National University for a postdoctoral fellowship, the Robert A. Welch Foundation, and NIH (GM31278).

PY - 2001/9/3

Y1 - 2001/9/3

N2 - The regioselectivity of the Pictet-Spengler cyclization for the synthesis of isoquinolines depends on the aryl substituent at C-2. The ratio of halotetrahydroisoquinoline 4 to isoquinoline 3 increases with increasing electrophilicity of the aromatic ring (H≪I<Br<Cl).

AB - The regioselectivity of the Pictet-Spengler cyclization for the synthesis of isoquinolines depends on the aryl substituent at C-2. The ratio of halotetrahydroisoquinoline 4 to isoquinoline 3 increases with increasing electrophilicity of the aromatic ring (H≪I<Br<Cl).

KW - Condensation

KW - Cyclization

KW - Halotetrahydroisoquinoline

KW - Pictet-Spengler

UR - http://www.scopus.com/inward/record.url?scp=0035801890&partnerID=8YFLogxK

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U2 - 10.1016/S0040-4039(01)01189-3

DO - 10.1016/S0040-4039(01)01189-3

M3 - Article

AN - SCOPUS:0035801890

SN - 0040-4039

VL - 42

SP - 6251

EP - 6253

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 36

ER -

Regioselectivity of Pictet-Spengler cyclization: Synthesis of halotetrahydroisoquinolines

Abstract

Keywords

ASJC Scopus subject areas

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