A highly efficient In(OTf)3-catalyzed [3 + 3] annulation of spirocyclopropyl oxindoles with 1,4-di-thiane-2,5-diol

Yongjia Hao; Yi Gong; Zhongyan Cao; Ying Zhou; Jian Zhou

doi:10.1016/j.cclet.2019.08.018

A highly efficient In(OTf)₃-catalyzed [3 + 3] annulation of spirocyclopropyl oxindoles with 1,4-di-thiane-2,5-diol

Yongjia Hao
, Yi Gong
, Zhongyan Cao
, Ying Zhou^*
, Jian Zhou

^*Corresponding author for this work

School of Chemistry and Molecular Engineering

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

17 Scopus citations

Abstract

Spirooxindoles play an important role in drug discovery and development. The development of efficient methods for the synthesis of spirooxindoles from easily available starting materials is of current interest. Herein, we report in detail the In(OTf)₃-catalyzed [3 + 3] annulation of spirocyclopropyl oxindoles and 1,4-di-thiane-2,5-diol, which allows the facile preparation of spiro[indoline-3,4′-thiopyran]-2-ones bearing (tetrahydro)thiopyran skeleton.

Original language	English
Pages (from-to)	681-684
Number of pages	4
Journal	Chinese Chemical Letters
Volume	31
Issue number	3
DOIs	https://doi.org/10.1016/j.cclet.2019.08.018
State	Published - Mar 2020

Keywords

Cyclopropane
Lewis acid catalysis
Spirooxindoles
Sulfur heterocycles
[3 + 3] cycloaddition

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10.1016/j.cclet.2019.08.018

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title = "A highly efficient In(OTf)3-catalyzed [3 + 3] annulation of spirocyclopropyl oxindoles with 1,4-di-thiane-2,5-diol",

abstract = "Spirooxindoles play an important role in drug discovery and development. The development of efficient methods for the synthesis of spirooxindoles from easily available starting materials is of current interest. Herein, we report in detail the In(OTf)3-catalyzed [3 + 3] annulation of spirocyclopropyl oxindoles and 1,4-di-thiane-2,5-diol, which allows the facile preparation of spiro[indoline-3,4′-thiopyran]-2-ones bearing (tetrahydro)thiopyran skeleton.",

keywords = "Cyclopropane, Lewis acid catalysis, Spirooxindoles, Sulfur heterocycles, [3 + 3] cycloaddition",

author = "Yongjia Hao and Yi Gong and Zhongyan Cao and Ying Zhou and Jian Zhou",

note = "Publisher Copyright: {\textcopyright} 2020 The Author",

year = "2020",

month = mar,

doi = "10.1016/j.cclet.2019.08.018",

language = "英语",

volume = "31",

pages = "681--684",

journal = "Chinese Chemical Letters",

issn = "1001-8417",

publisher = "Elsevier B.V.",

number = "3",

}

TY - JOUR

T1 - A highly efficient In(OTf)3-catalyzed [3 + 3] annulation of spirocyclopropyl oxindoles with 1,4-di-thiane-2,5-diol

AU - Hao, Yongjia

AU - Gong, Yi

AU - Cao, Zhongyan

AU - Zhou, Ying

AU - Zhou, Jian

PY - 2020/3

Y1 - 2020/3

N2 - Spirooxindoles play an important role in drug discovery and development. The development of efficient methods for the synthesis of spirooxindoles from easily available starting materials is of current interest. Herein, we report in detail the In(OTf)3-catalyzed [3 + 3] annulation of spirocyclopropyl oxindoles and 1,4-di-thiane-2,5-diol, which allows the facile preparation of spiro[indoline-3,4′-thiopyran]-2-ones bearing (tetrahydro)thiopyran skeleton.

AB - Spirooxindoles play an important role in drug discovery and development. The development of efficient methods for the synthesis of spirooxindoles from easily available starting materials is of current interest. Herein, we report in detail the In(OTf)3-catalyzed [3 + 3] annulation of spirocyclopropyl oxindoles and 1,4-di-thiane-2,5-diol, which allows the facile preparation of spiro[indoline-3,4′-thiopyran]-2-ones bearing (tetrahydro)thiopyran skeleton.

KW - Cyclopropane

KW - Lewis acid catalysis

KW - Spirooxindoles

KW - Sulfur heterocycles

KW - [3 + 3] cycloaddition

UR - https://www.scopus.com/pages/publications/85071907251

U2 - 10.1016/j.cclet.2019.08.018

DO - 10.1016/j.cclet.2019.08.018

M3 - 文章

AN - SCOPUS:85071907251

SN - 1001-8417

VL - 31

SP - 681

EP - 684

JO - Chinese Chemical Letters

JF - Chinese Chemical Letters

IS - 3

ER -

A highly efficient In(OTf)₃-catalyzed [3 + 3] annulation of spirocyclopropyl oxindoles with 1,4-di-thiane-2,5-diol

Abstract

Keywords

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