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^*

^*此作品的通信作者

化學系

研究成果: 雜誌貢獻 › 期刊論文 › 同行評審

5 引文斯高帕斯（Scopus）

摘要

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.

原文	英語
頁（從 - 到）	3201-3205
頁數	5
期刊	Synlett
發行號	19
DOIs	https://doi.org/10.1055/s-0029-1218294
出版狀態	已發佈 - 2009

ASJC Scopus subject areas

有機化學

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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",

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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

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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

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