BIOMAT Database Logo BIOMAT Database Logo

Synthesis of Pyrazolo[1,5-a]pyridinyl, Pyrazolo[1,5-a]quinolinyl, and Pyrazolo[5,1-a]isoquinolinyl Sulfonyl Fluorides via a [3 + 2] Annulation. 2023

Wen-Qian Wu, and Hua-Li Qin
School of Chemistry, Chemical Engineering and Life Sciences, Wuhan University of Technology, 205 Luoshi Road, Wuhan, 430070, P. R. China.

A [3 + 2] cycloaddition reaction of N-aminopyridines, N-aminoquinolines, and N-aminoisoquinolines with 1-bromoethene-1-sulfonyl fluoride (BESF) was performed to obtain optimum yields of various useful pyrazolo[1,5-a]pyridinyl, pyrazolo[1,5-a]quinolinyl, and pyrazolo[5,1-a]isoquinolinyl sulfonyl fluorides (43-90% yield). The transformation process showed broad substrate specificity, mild reaction conditions, and operational simplicity. Therefore, the reaction has great applicable value in the field of medicinal chemistry and other disciplines.

UI MeSH Term Description Entries

Related Publications

Wen-Qian Wu, and Hua-Li Qin
Regioselective Synthesis of Pyrazolo[1,5-a]pyridine via TEMPO-Mediated [3 + 2] Annulation-Aromatization of N-Aminopyridines and α,β-Unsaturated Compounds.
February 2022, Organic letters,
Wen-Qian Wu, and Hua-Li Qin
6-(Aryldiazenyl)pyrazolo[1,5-a]pyrimidines as Strategic Intermediates for the Synthesis of Pyrazolo[5,1-b]purines.
December 2016, The Journal of organic chemistry,
Wen-Qian Wu, and Hua-Li Qin
Copper-mediated oxidative [3 + 2]-annulation of nitroalkenes and pyridinium imines: efficient synthesis of 3-fluoro- and 3-nitro-pyrazolo[1,5-a]pyridines.
February 2020, Organic & biomolecular chemistry,
Wen-Qian Wu, and Hua-Li Qin
Synthesis, Characterization, Antimicrobial Activity and Anticancer of Some New Pyrazolo[1,5-a]pyrimidines and Pyrazolo[5,1-c]1,2,4-triazines.
January 2020, Medicinal chemistry (Shariqah (United Arab Emirates)),
Wen-Qian Wu, and Hua-Li Qin
An Approach for the Synthesis of Pyrazolo[1,5-a]pyrimidines via Cu(II)-Catalyzed [3+3] Annulation of Saturated Ketones with Aminopyrazoles.
September 2021, The Journal of organic chemistry,
Wen-Qian Wu, and Hua-Li Qin
Light-induced [2 + 2] cycloadditions for the construction of cyclobutane-fused pyridinyl sulfonyl fluorides.
June 2020, Organic & biomolecular chemistry,
Wen-Qian Wu, and Hua-Li Qin
An efficient strategy for the general synthesis of 3-aryl substituted pyrazolo[5,1-c][1,4]benzoxazines and pyrazolo[1,5-a][1,4]benzodiazepin-6(4H)-ones.
December 2011, Organic & biomolecular chemistry,
Wen-Qian Wu, and Hua-Li Qin
Synthesis of functionalized H-pyrazolo[5,1-a]isoquinolines via sequential reactions of N'-(2-alkynylbenzylidene)hydrazides.
November 2009, Organic & biomolecular chemistry,
Wen-Qian Wu, and Hua-Li Qin
Synthesis of some new pyrazolo[1,5-a]pyrimidine, pyrazolo[5,1-c]triazine, 1,3,4-thiadiazole and pyridine derivatives containing 1,2,3-triazole moiety.
June 2017, Chemistry Central journal,
Wen-Qian Wu, and Hua-Li Qin
Sulfonamide Synthesis via Calcium Triflimide Activation of Sulfonyl Fluorides.
July 2018, Organic letters,
Copied contents to your clipboard!