A facile method for the synthesis of 3-substituted 3-(Alkylthio)oxindoles or 3-alkoxyoxindoles

Feng Zhu; Feng Zhou; Zhong Yan Cao; Chao Wang; Yong Xue Zhang; Cui Hong Wang; Jian Zhou

doi:10.1055/s-0032-1316772

A facile method for the synthesis of 3-substituted 3-(Alkylthio)oxindoles or 3-alkoxyoxindoles

Feng Zhu
, Feng Zhou
, Zhong Yan Cao
, Chao Wang
, Yong Xue Zhang
, Cui Hong Wang^*
, Jian Zhou

^*Corresponding author for this work

School of Chemistry and Molecular Engineering

East China Normal University

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

54 Scopus citations

Abstract

We report a highly efficient perchloric acid catalyzed substitution reaction of 3-hydroxyoxindoles with thiols and alcohols for the synthesis of 3-substituted 3-(alkylthio)oxindoles or 3-alkoxyoxindoles, with catalyst loading down to 0.5 mol%. The scope and limitation of this method has been studied. An unprecedented mercury(II) perchlorate trihydrate catalyzed tandem Sakurai-Hosomi/(thio)ether formation reaction, starting from isatins, allyltrimethylsilane, and thiols or alcohols, has also been developed, which enables the facile synthesis of versatile 3-(alkylthio)- or 3-alkoxy-3- allyloxindoles.

Original language	English
Article number	SS-2012-E0588-FA
Pages (from-to)	3129-3144
Number of pages	16
Journal	Synthesis (Germany)
Volume	44
Issue number	20
DOIs	https://doi.org/10.1055/s-0032-1316772
State	Published - 2012

Keywords

3-(alkylthio)oxindoles
3-alkoxyoxindoles
3-hydroxyoxindoles
atom-efficient
tandem reaction

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10.1055/s-0032-1316772

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title = "A facile method for the synthesis of 3-substituted 3-(Alkylthio)oxindoles or 3-alkoxyoxindoles",

abstract = "We report a highly efficient perchloric acid catalyzed substitution reaction of 3-hydroxyoxindoles with thiols and alcohols for the synthesis of 3-substituted 3-(alkylthio)oxindoles or 3-alkoxyoxindoles, with catalyst loading down to 0.5 mol\%. The scope and limitation of this method has been studied. An unprecedented mercury(II) perchlorate trihydrate catalyzed tandem Sakurai-Hosomi/(thio)ether formation reaction, starting from isatins, allyltrimethylsilane, and thiols or alcohols, has also been developed, which enables the facile synthesis of versatile 3-(alkylthio)- or 3-alkoxy-3- allyloxindoles.",

keywords = "3-(alkylthio)oxindoles, 3-alkoxyoxindoles, 3-hydroxyoxindoles, atom-efficient, tandem reaction",

author = "Feng Zhu and Feng Zhou and Cao, \{Zhong Yan\} and Chao Wang and Zhang, \{Yong Xue\} and Wang, \{Cui Hong\} and Jian Zhou",

year = "2012",

doi = "10.1055/s-0032-1316772",

language = "英语",

volume = "44",

pages = "3129--3144",

journal = "Synthesis (Germany)",

issn = "0039-7881",

publisher = "Georg Thieme Verlag",

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TY - JOUR

T1 - A facile method for the synthesis of 3-substituted 3-(Alkylthio)oxindoles or 3-alkoxyoxindoles

AU - Zhu, Feng

AU - Zhou, Feng

AU - Cao, Zhong Yan

AU - Wang, Chao

AU - Zhang, Yong Xue

AU - Wang, Cui Hong

AU - Zhou, Jian

PY - 2012

Y1 - 2012

N2 - We report a highly efficient perchloric acid catalyzed substitution reaction of 3-hydroxyoxindoles with thiols and alcohols for the synthesis of 3-substituted 3-(alkylthio)oxindoles or 3-alkoxyoxindoles, with catalyst loading down to 0.5 mol%. The scope and limitation of this method has been studied. An unprecedented mercury(II) perchlorate trihydrate catalyzed tandem Sakurai-Hosomi/(thio)ether formation reaction, starting from isatins, allyltrimethylsilane, and thiols or alcohols, has also been developed, which enables the facile synthesis of versatile 3-(alkylthio)- or 3-alkoxy-3- allyloxindoles.

AB - We report a highly efficient perchloric acid catalyzed substitution reaction of 3-hydroxyoxindoles with thiols and alcohols for the synthesis of 3-substituted 3-(alkylthio)oxindoles or 3-alkoxyoxindoles, with catalyst loading down to 0.5 mol%. The scope and limitation of this method has been studied. An unprecedented mercury(II) perchlorate trihydrate catalyzed tandem Sakurai-Hosomi/(thio)ether formation reaction, starting from isatins, allyltrimethylsilane, and thiols or alcohols, has also been developed, which enables the facile synthesis of versatile 3-(alkylthio)- or 3-alkoxy-3- allyloxindoles.

KW - 3-(alkylthio)oxindoles

KW - 3-alkoxyoxindoles

KW - 3-hydroxyoxindoles

KW - atom-efficient

KW - tandem reaction

UR - https://www.scopus.com/pages/publications/84867336857

U2 - 10.1055/s-0032-1316772

DO - 10.1055/s-0032-1316772

M3 - 文章

AN - SCOPUS:84867336857

SN - 0039-7881

VL - 44

SP - 3129

EP - 3144

JO - Synthesis (Germany)

JF - Synthesis (Germany)

IS - 20

M1 - SS-2012-E0588-FA

ER -

A facile method for the synthesis of 3-substituted 3-(Alkylthio)oxindoles or 3-alkoxyoxindoles

Abstract

Keywords

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