American Chemical Society (ACS)
Organic Letters
,  volume 27 ,  issue 9 ,  pages 2031-2036

Domino Synthesis of Thioindirubin via Aldol Condensation/C–S Cross-Coupling/Cyclization Reaction Using Xanthate as a Sulfur Surrogate

Palanisamy Soundarya 1, 2, 3, 4
, 
Sayan Pahan 1, 2, 3, 4
, 
G Sekar 1, 2, 3, 4
1
 
DEPARTMENT OF CHEMISTRY
2
 
3
 
Department of Chemistry, Chennai, India | 
4
 
Publication type: Journal Article
Publication date: 2025-02-24
American Chemical Society (ACS)
scimago Q1
wos Q1
SJR: 1.235
CiteScore: 8.7
Impact factor: 5.0
ISSN: 15237060, 15237052
Abstract
Developing new types of molecular photoswitches with novel functionalities allows experts to advance their applications in biology, chemistry, and material sciences. Herein, we report an efficient synthetic protocol for the synthesis of thioindirubin derivatives from commercially available starting materials. This domino reaction proceeds through aldol condensation followed by intramolecular C-S bond formation and selective cyclization in a 5-exo-trig manner. Nuclear magnetic resonance studies suggest the ability to tune both isomerization directions upon irradiation with different ultraviolet and visible light (370-640 nm light-emitting diode). The newly reported hemithioindigo photoswitches have various applications in the areas of life science and material sciences.
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Soundarya P. et al. Domino Synthesis of Thioindirubin via Aldol Condensation/C–S Cross-Coupling/Cyclization Reaction Using Xanthate as a Sulfur Surrogate // Organic Letters. 2025. Vol. 27. No. 9. pp. 2031-2036.
GOST all authors (up to 50) Copy
Soundarya P., Pahan S., Sekar G. Domino Synthesis of Thioindirubin via Aldol Condensation/C–S Cross-Coupling/Cyclization Reaction Using Xanthate as a Sulfur Surrogate // Organic Letters. 2025. Vol. 27. No. 9. pp. 2031-2036.
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RIS Copy
TY - JOUR
DO - 10.1021/acs.orglett.4c04539
UR - https://pubs.acs.org/doi/10.1021/acs.orglett.4c04539
TI - Domino Synthesis of Thioindirubin via Aldol Condensation/C–S Cross-Coupling/Cyclization Reaction Using Xanthate as a Sulfur Surrogate
T2 - Organic Letters
AU - Soundarya, Palanisamy
AU - Pahan, Sayan
AU - Sekar, G
PY - 2025
DA - 2025/02/24
PB - American Chemical Society (ACS)
SP - 2031-2036
IS - 9
VL - 27
SN - 1523-7060
SN - 1523-7052
ER -
BibTex |
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BibTex (up to 50 authors) Copy
@article{2025_Soundarya,
author = {Palanisamy Soundarya and Sayan Pahan and G Sekar},
title = {Domino Synthesis of Thioindirubin via Aldol Condensation/C–S Cross-Coupling/Cyclization Reaction Using Xanthate as a Sulfur Surrogate},
journal = {Organic Letters},
year = {2025},
volume = {27},
publisher = {American Chemical Society (ACS)},
month = {feb},
url = {https://pubs.acs.org/doi/10.1021/acs.orglett.4c04539},
number = {9},
pages = {2031--2036},
doi = {10.1021/acs.orglett.4c04539}
}
MLA
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MLA Copy
Soundarya, Palanisamy, et al. “Domino Synthesis of Thioindirubin via Aldol Condensation/C–S Cross-Coupling/Cyclization Reaction Using Xanthate as a Sulfur Surrogate.” Organic Letters, vol. 27, no. 9, Feb. 2025, pp. 2031-2036. https://pubs.acs.org/doi/10.1021/acs.orglett.4c04539.