Base-catalyzed conjugate addition of thiols to indolyl acrylic acids and in situ decarboxylation: An expedient synthesis of functionalized 3-(1-thio)ethyl-1H-indoles

Shijay Gao; Chi Tseng; B. Rama Raju; Chen Hsuan Tsai; Ching Fa Yao

doi:10.1055/s-0029-1218294

Base-catalyzed conjugate addition of thiols to indolyl acrylic acids and in situ decarboxylation: An expedient synthesis of functionalized 3-(1-thio)ethyl-1H-indoles

Shijay Gao
, Chi Tseng
, B. Rama Raju
, Chen Hsuan Tsai
, Ching Fa Yao^*

^*Corresponding author for this work

Department of Chemistry

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

5 Citations (Scopus)

Abstract

A one-pot, two-step method for the synthesis of 3-(1-thio)ethyl- 1H-indoles is described herein. This simple procedure in-volves the Michael addition of thiols to 3-indoleacrylic acids fol-lowed by in situ decarboxylation of the Michael adduct in the presence of a catalytic amount of K₂CO ₃ in DMF at 100 °C. The method was found to be fairly general with various thiols and dif-ferent 3-indoleacrylic acids.

Original language	English
Pages (from-to)	3201-3205
Number of pages	5
Journal	Synlett
Issue number	19
DOIs	https://doi.org/10.1055/s-0029-1218294
Publication status	Published - 2009

Keywords

3-[1-(thio)ethyl]-1H-indole
Conjugate addition
Decarboxylation
Indole
Thiol

ASJC Scopus subject areas

Organic Chemistry

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10.1055/s-0029-1218294

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title = "Base-catalyzed conjugate addition of thiols to indolyl acrylic acids and in situ decarboxylation: An expedient synthesis of functionalized 3-(1-thio)ethyl-1H-indoles",

abstract = "A one-pot, two-step method for the synthesis of 3-(1-thio)ethyl- 1H-indoles is described herein. This simple procedure in-volves the Michael addition of thiols to 3-indoleacrylic acids fol-lowed by in situ decarboxylation of the Michael adduct in the presence of a catalytic amount of K2CO 3 in DMF at 100 °C. The method was found to be fairly general with various thiols and dif-ferent 3-indoleacrylic acids.",

keywords = "3-[1-(thio)ethyl]-1H-indole, Conjugate addition, Decarboxylation, Indole, Thiol",

author = "Shijay Gao and Chi Tseng and \{Rama Raju\}, B. and Tsai, \{Chen Hsuan\} and Yao, \{Ching Fa\}",

year = "2009",

doi = "10.1055/s-0029-1218294",

language = "English",

pages = "3201--3205",

journal = "Synlett",

issn = "0936-5214",

publisher = "Georg Thieme Verlag",

number = "19",

}

TY - JOUR

T1 - Base-catalyzed conjugate addition of thiols to indolyl acrylic acids and in situ decarboxylation

T2 - An expedient synthesis of functionalized 3-(1-thio)ethyl-1H-indoles

AU - Gao, Shijay

AU - Tseng, Chi

AU - Rama Raju, B.

AU - Tsai, Chen Hsuan

AU - Yao, Ching Fa

PY - 2009

Y1 - 2009

N2 - A one-pot, two-step method for the synthesis of 3-(1-thio)ethyl- 1H-indoles is described herein. This simple procedure in-volves the Michael addition of thiols to 3-indoleacrylic acids fol-lowed by in situ decarboxylation of the Michael adduct in the presence of a catalytic amount of K2CO 3 in DMF at 100 °C. The method was found to be fairly general with various thiols and dif-ferent 3-indoleacrylic acids.

AB - A one-pot, two-step method for the synthesis of 3-(1-thio)ethyl- 1H-indoles is described herein. This simple procedure in-volves the Michael addition of thiols to 3-indoleacrylic acids fol-lowed by in situ decarboxylation of the Michael adduct in the presence of a catalytic amount of K2CO 3 in DMF at 100 °C. The method was found to be fairly general with various thiols and dif-ferent 3-indoleacrylic acids.

KW - 3-[1-(thio)ethyl]-1H-indole

KW - Conjugate addition

KW - Decarboxylation

KW - Indole

KW - Thiol

UR - https://www.scopus.com/pages/publications/72049088231

UR - https://www.scopus.com/pages/publications/72049088231#tab=citedBy

U2 - 10.1055/s-0029-1218294

DO - 10.1055/s-0029-1218294

M3 - Article

AN - SCOPUS:72049088231

SN - 0936-5214

SP - 3201

EP - 3205

JO - Synlett

JF - Synlett

IS - 19

ER -

Base-catalyzed conjugate addition of thiols to indolyl acrylic acids and in situ decarboxylation: An expedient synthesis of functionalized 3-(1-thio)ethyl-1H-indoles

Abstract

Keywords

ASJC Scopus subject areas

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