Synthetic optimization of rosiglitazone and related intermediates for industrial purposes
Publication type: Journal Article
Publication date: 2015-06-17
scimago Q2
wos Q2
SJR: 0.528
CiteScore: 5.7
Impact factor: 3.5
ISSN: 09226168, 15685675
General Chemistry
Abstract
As an important newly Food and Drug Administration (FDA)-approved drug for treating diabetes, rosiglitazone (1) has received much attention from researchers in many areas. To search for an economical and convenient synthesis method for 1, we explored the reaction conditions and workup of a scalable five-step synthetic route by an orthogonal method to determine the best condition for each reaction step. The starting materials are commercially available, including 2-chloropyridine (2), N-methylethanolamine (3), 4-fluorobenzaldehyde (4a) or 4-hydroxybenzaldehyde (4b), and 1,3-thiazolidine-2,4-dione (5). The five sequential reaction steps are cyclization, alkylation, etherification, condensation, and reduction, having optimal yield of 90, 99, 59, 75, and 91 %, respectively. The best overall yield to synthesize rosiglitazone based on compound 2 was 40 %, being suitable for industrial purposes, using water as a green solvent and avoiding column chromatography during the last three reaction steps.
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8
Total citations:
8
Citations from 2025:
2
(25%)
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GOST
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Ge M. et al. Synthetic optimization of rosiglitazone and related intermediates for industrial purposes // Research on Chemical Intermediates. 2015. Vol. 42. No. 3. pp. 2023-2033.
GOST all authors (up to 50)
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Ge M., Zheng M., Dong M., Gao Y., Zheng A., Li Z., Hu R. Synthetic optimization of rosiglitazone and related intermediates for industrial purposes // Research on Chemical Intermediates. 2015. Vol. 42. No. 3. pp. 2023-2033.
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RIS
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TY - JOUR
DO - 10.1007/s11164-015-2132-0
UR - https://doi.org/10.1007/s11164-015-2132-0
TI - Synthetic optimization of rosiglitazone and related intermediates for industrial purposes
T2 - Research on Chemical Intermediates
AU - Ge, Meng
AU - Zheng, Meilin
AU - Dong, Mengshu
AU - Gao, Yang
AU - Zheng, Aqun
AU - Li, Zhenyu
AU - Hu, Ruizhi
PY - 2015
DA - 2015/06/17
PB - Springer Nature
SP - 2023-2033
IS - 3
VL - 42
SN - 0922-6168
SN - 1568-5675
ER -
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BibTex (up to 50 authors)
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@article{2015_Ge,
author = {Meng Ge and Meilin Zheng and Mengshu Dong and Yang Gao and Aqun Zheng and Zhenyu Li and Ruizhi Hu},
title = {Synthetic optimization of rosiglitazone and related intermediates for industrial purposes},
journal = {Research on Chemical Intermediates},
year = {2015},
volume = {42},
publisher = {Springer Nature},
month = {jun},
url = {https://doi.org/10.1007/s11164-015-2132-0},
number = {3},
pages = {2023--2033},
doi = {10.1007/s11164-015-2132-0}
}
Cite this
MLA
Copy
Ge, Meng, et al. “Synthetic optimization of rosiglitazone and related intermediates for industrial purposes.” Research on Chemical Intermediates, vol. 42, no. 3, Jun. 2015, pp. 2023-2033. https://doi.org/10.1007/s11164-015-2132-0.