Temperature-Controlled Thiation of α-Cyano-β-Alkynyl Carbonyl Derivatives for de Novo Synthesis of 2-Aminothiophenes and Thieno[2,3- c]isothiazoles

Tzu Ting Kao; Bo Kai Peng; Min Chieh Liang; Chia Jui Lee; I. Chia Chen; Kak Shan Shia; Yen-Ku Wu

doi:10.1021/acs.joc.8b01866

Temperature-Controlled Thiation of α-Cyano-β-Alkynyl Carbonyl Derivatives for de Novo Synthesis of 2-Aminothiophenes and Thieno[2,3- c]isothiazoles

Tzu Ting Kao, Bo Kai Peng, Min Chieh Liang, Chia Jui Lee, I. Chia Chen, Kak Shan Shia^*, Yen-Ku Wu

^*Corresponding author for this work

Department of Applied Chemistry

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

6 Scopus citations

Abstract

Making use of temperature-controlled thiation as a key operation, a simple route to 2-aminothiophenes or thieno[2,3-c]isothiazoles has been newly developed wherein the 2-aminothiophene nucleus was formed through an initial formation of thioamide followed by a 5-exo-dig addition to the tethered alkyne; however, under harsher thermal conditions, excess sulfur-transferring reagents enabled further oxidative thiation to generate the corresponding thieno[2,3-c]isothiazoles.

Original language	English
Pages (from-to)	14688-14697
Number of pages	10
Journal	Journal of Organic Chemistry
Volume	83
Issue number	23
DOIs	https://doi.org/10.1021/acs.joc.8b01866
State	Published - 7 Dec 2018

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@article{443cb6f754bc4c369aec6829464119f4,

title = "Temperature-Controlled Thiation of α-Cyano-β-Alkynyl Carbonyl Derivatives for de Novo Synthesis of 2-Aminothiophenes and Thieno[2,3- c]isothiazoles",

abstract = "Making use of temperature-controlled thiation as a key operation, a simple route to 2-aminothiophenes or thieno[2,3-c]isothiazoles has been newly developed wherein the 2-aminothiophene nucleus was formed through an initial formation of thioamide followed by a 5-exo-dig addition to the tethered alkyne; however, under harsher thermal conditions, excess sulfur-transferring reagents enabled further oxidative thiation to generate the corresponding thieno[2,3-c]isothiazoles.",

author = "Kao, {Tzu Ting} and Peng, {Bo Kai} and Liang, {Min Chieh} and Lee, {Chia Jui} and Chen, {I. Chia} and Shia, {Kak Shan} and Yen-Ku Wu",

year = "2018",

month = dec,

day = "7",

doi = "10.1021/acs.joc.8b01866",

language = "English",

volume = "83",

pages = "14688--14697",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "23",

}

Temperature-Controlled Thiation of α-Cyano-β-Alkynyl Carbonyl Derivatives for de Novo Synthesis of 2-Aminothiophenes and Thieno[2,3- c]isothiazoles. / Kao, Tzu Ting; Peng, Bo Kai; Liang, Min Chieh; Lee, Chia Jui; Chen, I. Chia; Shia, Kak Shan; Wu, Yen-Ku.

In: Journal of Organic Chemistry, Vol. 83, No. 23, 07.12.2018, p. 14688-14697.

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

TY - JOUR

T1 - Temperature-Controlled Thiation of α-Cyano-β-Alkynyl Carbonyl Derivatives for de Novo Synthesis of 2-Aminothiophenes and Thieno[2,3- c]isothiazoles

AU - Kao, Tzu Ting

AU - Peng, Bo Kai

AU - Liang, Min Chieh

AU - Lee, Chia Jui

AU - Chen, I. Chia

AU - Shia, Kak Shan

AU - Wu, Yen-Ku

PY - 2018/12/7

Y1 - 2018/12/7

N2 - Making use of temperature-controlled thiation as a key operation, a simple route to 2-aminothiophenes or thieno[2,3-c]isothiazoles has been newly developed wherein the 2-aminothiophene nucleus was formed through an initial formation of thioamide followed by a 5-exo-dig addition to the tethered alkyne; however, under harsher thermal conditions, excess sulfur-transferring reagents enabled further oxidative thiation to generate the corresponding thieno[2,3-c]isothiazoles.

AB - Making use of temperature-controlled thiation as a key operation, a simple route to 2-aminothiophenes or thieno[2,3-c]isothiazoles has been newly developed wherein the 2-aminothiophene nucleus was formed through an initial formation of thioamide followed by a 5-exo-dig addition to the tethered alkyne; however, under harsher thermal conditions, excess sulfur-transferring reagents enabled further oxidative thiation to generate the corresponding thieno[2,3-c]isothiazoles.

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VL - 83

SP - 14688

EP - 14697

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 23

ER -

Temperature-Controlled Thiation of α-Cyano-β-Alkynyl Carbonyl Derivatives for de Novo Synthesis of 2-Aminothiophenes and Thieno[2,3- c]isothiazoles

Abstract

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