56983-95-0Relevant academic research and scientific papers
Regioselective Metalation and Functionalization of the Pyrazolo[1,5- a]pyridine Scaffold Using Mg- and Zn-TMP Bases
Balkenhohl, Moritz,Salgues, Bruno,Hirai, Takahiro,Karaghiosoff, Konstantin,Knochel, Paul
supporting information, p. 3114 - 3118 (2018/05/28)
A regioselective functionalization of the pyrazolo[1,5-a]pyridine scaffold using Mg- and Zn-TMP bases (TMP = 2,2,6,6-tetramethylpiperidyl) in the presence or absence of BF3·OEt2 is described. Also, various functionalized pyrazolo[1,5-a]pyridines bearing an ester function (and an NHBoc or ethyl group) are magnesiated and functionalized, leading to polysubstituted heterocycles. Additionally, a sulfoxide directed ortho-metalation, followed by the transition-metal-free amination of a pyrazolo[1,5-a]pyridine sulfoxide, using a magnesium amide, is reported.
Synthesis of 2-Arylpyrazolo[1,5- a ]pyridines by Suzuki-Miyaura Cross-Coupling Reaction
Umei, Kentaro,Nishigaya, Yosuke,Kamiya, Megumi,Kohno, Yasushi,Seto, Shigeki
, p. 3221 - 3230 (2015/10/19)
Convenient access to a variety of 2-arylated pyrazolo[1,5-a]pyridine via pyrazolo[1,5-a]pyridine-2-yl triflate using the Suzuki-MiyauraA AA cross-coupling reaction is described. Fifteen 2-arylpyrazolo[1,5-a]pyridine derivatives were synthesized in 52-95% yields.
BICYCLIC HETEROARYL UREA, THIOUREA, GUANIDINE AND CYANOGUANIDINE COMPOUNDS AS TRKA KINASE INHIBITORS
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Paragraph 00675, (2014/06/11)
Compounds of Formula I or stereoisomers, tautomers, or pharmaceutically acceptable salts, solvates or prodrugs thereof, wherein Ring A, Ring C and X are as defined herein, are inhibitors of TrkA kinase and are useful in the treatment of diseases which can be treated with a TrkA kinase inhibitor such as pain, cancer, inflammation/inflammatory diseases, neurodegenerative diseases, certain infectious diseases, Sjogren's syndrome, endometriosis, diabetic peripheral neuropathy, prostatitis and pelvic pain syndrome.
Synthesis of pyrazolo[1,5-a]pyridines by thermal intramolecular cyclization
Hoashi, Yasutaka,Takai, Takafumi,Kotani, Etsuo,Koike, Tatsuki
supporting information, p. 2199 - 2202 (2013/05/09)
Thermal intramolecular cyclization of N-amino-2-alkynylpyridines was developed for facile and versatile synthesis of pyrazolo[1,5-a]pyridines. Simply heating N-amino-2-alkynylpyridines in acetic acid provided pyrazolo[1,5-a] pyridines in excellent yield.
From N-benzoylpyridinium imides to pyrazolo[1,5-a]pyridines: A mechanistic discussion on a stoichiometric Cu protocol
Ling, Lin,Chen, Jingqing,Song, Jiahui,Zhang, Yuhai,Li, Xinqian,Song, Lijuan,Shi, Feng,Li, Yuxue,Wu, Chunrui
, p. 3894 - 3902 (2014/03/21)
A Cu-mediated preparation of 2-substitiuted pyrazolo[1,5-a]pyridines from N-benzoylpyridinium imides and terminal alkynes is described using stoichiometric Cu(OAc)2 as both the mediator and the oxidant. Extensive DFT calculations suggest a Cu(i
PYRAZOLOPYRIDINE DERIVATIVE OR PHARMACOLOGICALLY ACCEPTABLE SALT THEREOF
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Paragraph 0211; 0212, (2014/01/07)
A pyrazolopyridine derivative represented by the following formula (I) or a pharmacologically acceptable salt thereof exhibits a strong EP1 receptor antagonistic effect. Thus, the derivative or the pharmacologically acceptable salt is useful as
Copper-catalyzed direct oxidative annulation of N-iminopyridinium ylides with terminal alkynes using O2 as oxidant
Ding, Shengtao,Yan, Yuepeng,Jiao, Ning
, p. 4250 - 4252 (2013/05/22)
The aerobic direct dehydrogenative annulation of N-iminopyridinium ylides with terminal alkynes leading to pyrazolo[1,5-a]pyridine derivatives has been developed.
Au(i)-catalyzed and iodine-mediated cyclization of enynylpyrazoles to provide pyrazolo[1,5-a]pyridines
Wu, Hung-Chou,Yang, Chia-Wen,Hwang, Long-Chih,Wu, Ming-Jung
experimental part, p. 6640 - 6648 (2012/09/22)
Pyrazolo[1,5-a]pyridines and 6-iodopyrazolo[1,5-a]pyridines were synthesized by gold-catalyzed and iodine-mediated cyclization of enynylpyrazoles in good to excellent yields, respectively. The iodinated adducts were further converted to 6-arylpyrazolo[1,5
Synthesis of 2- and 2,3-substituted Pyrazolo[1,5- a ]pyridines: Scope and mechanistic considerations of a domino direct alkynylation and cyclization of n -iminopyridinium ylides using alkenyl bromides, alkenyl iodides, and alkynes
Mousseau, James J.,Bull, James A.,Ladd, Carolyn L.,Fortier, Angelique,Sustac Roman, Daniela,Charette, Andre B.
, p. 8243 - 8261 (2012/01/03)
Direct functionalization and tandem processes have both received considerable recent interest due to their cost and time efficiency. Herein we report the synthesis of difficult to obtain 2-substituted pyrazolo[1,5-a] pyridines through a tandem palladium-catalyzed/silver-mediated elimination/direct functionalization/cyclization reaction involving N-benzoyliminopyridinium ylides. As such, these biologically important molecules are prepared in an efficient, high-yielding manner, only requiring a two-step sequence from pyridine. Aryl-substituted alkenyl bromides and iodides are effective ylide coupling partners. Mechanistic studies led to the use of terminal alkynes, which extended the scope of the reaction to include alkyl substitution on the unsaturated reactive site. The optimization, scope, and mechanistic considerations of the process are discussed.
Synthesis of 2-Substituted Pyrazolo[1,5-a]pyridines through Cascade Direct Alkenylation/Cyclization Reactions
Mousseau, James J.,Fortier, Angelique,Charette, Andre B.
supporting information; experimental part, p. 516 - 519 (2010/05/02)
[Chemical equation presented] The synthesis of 2-substituted pyrazolo[1,5-a]pyridines from N-iminopyridinium ylides is described. These medicinally interesting compounds are formed through a cascade process involving a palladium-catalyzed direct alkenylation reaction followed by silver-mediated cyclization. The reaction can be performed with a wide range of electron-poor and electron-rich alkenyl iodides in good yields. This work represents perhaps the most direct route for the preparation of these compounds.
