Molecular Iodine-Promoted [3 + 2] Oxidative Cyclization for the Synthesis of Heteroarene-Fused [1,2,4] Thiadiazoles/Selenadiazoles
Jin-Yu Chen
1
,
Manikandan Selvaraju
2
,
Yen Tzu Lin
1
,
Sandip Dhole
1
,
Chih-Yu Lin
1
,
Chung-Ren Sun
1, 3
Publication type: Journal Article
Publication date: 2020-04-06
scimago Q2
wos Q1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
32249566
Organic Chemistry
Abstract
Two new classes of heteroarene-fused [1,2,4]thiadiazole and [1,2,4]selenadiazole are synthesized through the iodine-mediated [3 + 2] oxidative cyclization of 2-aminoheteroarenes and isothiocyanates/isoselenocyanates. This oxidative [3 + 2] annulation strategy is highly regiospecific to proceed a selective C-N bond formation at the endo-nitrogen of 2-aminoheteroarenes followed by an intramolecular oxidative N-S/N-Se bond formation. It is the first example of an I2-mediated oxidative nitrogen-selenium (N-Se) bond formation.
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12
Total citations:
12
Citations from 2024:
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(33%)
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GOST
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Chen J. et al. Molecular Iodine-Promoted [3 + 2] Oxidative Cyclization for the Synthesis of Heteroarene-Fused [1,2,4] Thiadiazoles/Selenadiazoles // Journal of Organic Chemistry. 2020. Vol. 85. No. 8. pp. 5570-5579.
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Chen J., Selvaraju M., Lin Y. T., Dhole S., Lin C., Sun C. Molecular Iodine-Promoted [3 + 2] Oxidative Cyclization for the Synthesis of Heteroarene-Fused [1,2,4] Thiadiazoles/Selenadiazoles // Journal of Organic Chemistry. 2020. Vol. 85. No. 8. pp. 5570-5579.
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TY - JOUR
DO - 10.1021/acs.joc.0c00421
UR - https://doi.org/10.1021/acs.joc.0c00421
TI - Molecular Iodine-Promoted [3 + 2] Oxidative Cyclization for the Synthesis of Heteroarene-Fused [1,2,4] Thiadiazoles/Selenadiazoles
T2 - Journal of Organic Chemistry
AU - Chen, Jin-Yu
AU - Selvaraju, Manikandan
AU - Lin, Yen Tzu
AU - Dhole, Sandip
AU - Lin, Chih-Yu
AU - Sun, Chung-Ren
PY - 2020
DA - 2020/04/06
PB - American Chemical Society (ACS)
SP - 5570-5579
IS - 8
VL - 85
PMID - 32249566
SN - 0022-3263
SN - 1520-6904
ER -
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BibTex (up to 50 authors)
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@article{2020_Chen,
author = {Jin-Yu Chen and Manikandan Selvaraju and Yen Tzu Lin and Sandip Dhole and Chih-Yu Lin and Chung-Ren Sun},
title = {Molecular Iodine-Promoted [3 + 2] Oxidative Cyclization for the Synthesis of Heteroarene-Fused [1,2,4] Thiadiazoles/Selenadiazoles},
journal = {Journal of Organic Chemistry},
year = {2020},
volume = {85},
publisher = {American Chemical Society (ACS)},
month = {apr},
url = {https://doi.org/10.1021/acs.joc.0c00421},
number = {8},
pages = {5570--5579},
doi = {10.1021/acs.joc.0c00421}
}
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MLA
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Chen, Jin-Yu, et al. “Molecular Iodine-Promoted [3 + 2] Oxidative Cyclization for the Synthesis of Heteroarene-Fused [1,2,4] Thiadiazoles/Selenadiazoles.” Journal of Organic Chemistry, vol. 85, no. 8, Apr. 2020, pp. 5570-5579. https://doi.org/10.1021/acs.joc.0c00421.