Cu-Catalyzed Three-Component Cascade Synthesis of 1,3-Benzothiazines from ortho-Aminohydrazones and Bromodifluoroacetamides
Publication type: Journal Article
Publication date: 2022-10-14
scimago Q1
wos Q1
SJR: 1.235
CiteScore: 8.7
Impact factor: 5.0
ISSN: 15237060, 15237052
PubMed ID:
36239477
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
An efficient and convenient synthesis of benzo[d][1,3]thiazine has been developed by employing a copper-catalyzed transformation of readily available ketone-derived hydrazones with elemental sulfur and bromodifluoroalkylative reagents. The strategy involves an S8-catalyzed selective triple-cleavage of bromodifluoroacetamides, which acts as a C1 synthon at the 2-position of benzo[d][1,3]thiazine. A mechanism proceeding through a Cu-carbene intermediate is proposed for the C-S bond formation.
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12
Total citations:
12
Citations from 2025:
5
(41.67%)
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Yu C. et al. Cu-Catalyzed Three-Component Cascade Synthesis of 1,3-Benzothiazines from ortho-Aminohydrazones and Bromodifluoroacetamides // Organic Letters. 2022. Vol. 24. No. 42. pp. 7861-7865.
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Yu C., Ke F., Su J., Ma X., Li X., Song Q. Cu-Catalyzed Three-Component Cascade Synthesis of 1,3-Benzothiazines from ortho-Aminohydrazones and Bromodifluoroacetamides // Organic Letters. 2022. Vol. 24. No. 42. pp. 7861-7865.
Cite this
RIS
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TY - JOUR
DO - 10.1021/acs.orglett.2c03399
UR - https://doi.org/10.1021/acs.orglett.2c03399
TI - Cu-Catalyzed Three-Component Cascade Synthesis of 1,3-Benzothiazines from ortho-Aminohydrazones and Bromodifluoroacetamides
T2 - Organic Letters
AU - Yu, Changjiang
AU - Ke, Fumei
AU - Su, Jianke
AU - Ma, Xingxing
AU - Li, Xin
AU - Song, Qiuling
PY - 2022
DA - 2022/10/14
PB - American Chemical Society (ACS)
SP - 7861-7865
IS - 42
VL - 24
PMID - 36239477
SN - 1523-7060
SN - 1523-7052
ER -
Cite this
BibTex (up to 50 authors)
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@article{2022_Yu,
author = {Changjiang Yu and Fumei Ke and Jianke Su and Xingxing Ma and Xin Li and Qiuling Song},
title = {Cu-Catalyzed Three-Component Cascade Synthesis of 1,3-Benzothiazines from ortho-Aminohydrazones and Bromodifluoroacetamides},
journal = {Organic Letters},
year = {2022},
volume = {24},
publisher = {American Chemical Society (ACS)},
month = {oct},
url = {https://doi.org/10.1021/acs.orglett.2c03399},
number = {42},
pages = {7861--7865},
doi = {10.1021/acs.orglett.2c03399}
}
Cite this
MLA
Copy
Yu., Changjiang, et al. “Cu-Catalyzed Three-Component Cascade Synthesis of 1,3-Benzothiazines from ortho-Aminohydrazones and Bromodifluoroacetamides.” Organic Letters, vol. 24, no. 42, Oct. 2022, pp. 7861-7865. https://doi.org/10.1021/acs.orglett.2c03399.