Organic Letters

, том 7 , издание 5 , страницы 791-794

Synthesis of thienothiopyranthiones by a new molecular rearrangement

Тип публикации: Journal Article

Дата публикации: 2005-02-01

American Chemical Society (ACS)

Organic Letters

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SJR: 1.235

CiteScore: 8.7

Impact factor: 5.0

ISSN: 15237060, 15237052

DOI: 10.1021/ol0476669

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PubMed ID: 15727442

Organic Chemistry

Biochemistry

Physical and Theoretical Chemistry

Краткое описание

On heating with alkynes, the readily prepared 1,3-dithioles 3 undergo a new cycloaddition reaction and an unprecedented molecular rearrangement with loss of chlorine to give the first 7H-thieno[2,3-c]thiopyran-7-thiones 4 and 4H-thieno[3,2-c]thiopyran-4-thiones 5 whose structures were confirmed by X-ray diffraction. Unexpectedly, the different alkynes used to form 3 and to convert it into 4 and 5 were incorporated regiospecifically into the thiophene and thiopyran rings, respectively. [reaction: see text]

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Тихоокеанский институт биоорганической химии им. Г.Б. Елякова ДВО РАН

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Ogurtsov V. A. et al. Synthesis of thienothiopyranthiones by a new molecular rearrangement // Organic Letters. 2005. Vol. 7. No. 5. pp. 791-794.

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Ogurtsov V. A., Rakitin O. A., Rees C. W., Smolentsev A. A., Belyakov P. A., Golovanov D. G., Lyssenko K. A. Synthesis of thienothiopyranthiones by a new molecular rearrangement // Organic Letters. 2005. Vol. 7. No. 5. pp. 791-794.

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TY - JOUR

DO - 10.1021/ol0476669

UR - https://doi.org/10.1021/ol0476669

TI - Synthesis of thienothiopyranthiones by a new molecular rearrangement

T2 - Organic Letters

AU - Ogurtsov, Vladimir A.

AU - Rakitin, Oleg A.

AU - Rees, Charles W.

AU - Smolentsev, Alexey A.

AU - Belyakov, Pavel A

AU - Golovanov, Denis G.

AU - Lyssenko, Konstantin A.

PY - 2005

DA - 2005/02/01

PB - American Chemical Society (ACS)

SP - 791-794

IS - 5

VL - 7

PMID - 15727442

SN - 1523-7060

SN - 1523-7052

ER -

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@article{2005_Ogurtsov,

author = {Vladimir A. Ogurtsov and Oleg A. Rakitin and Charles W. Rees and Alexey A. Smolentsev and Pavel A Belyakov and Denis G. Golovanov and Konstantin A. Lyssenko},

title = {Synthesis of thienothiopyranthiones by a new molecular rearrangement},

journal = {Organic Letters},

year = {2005},

volume = {7},

publisher = {American Chemical Society (ACS)},

month = {feb},

url = {https://doi.org/10.1021/ol0476669},

number = {5},

pages = {791--794},

doi = {10.1021/ol0476669}

}

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Ogurtsov, Vladimir A., et al. “Synthesis of thienothiopyranthiones by a new molecular rearrangement.” Organic Letters, vol. 7, no. 5, Feb. 2005, pp. 791-794. https://doi.org/10.1021/ol0476669.