BIOMAT Database Logo BIOMAT Database Logo

Cu(I)-catalyzed regioselective synthesis of pyrazolo[5,1-c]-1,2,4-triazoles. 2012

Davit Jishkariani, and C Dennis Hall, and Alexander A Oliferenko, and David Leino, and Alan R Katritzky
Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, Florida 32611-7200, USA.

Cycloadditions of terminal alkynes to 1,2,4-triazolium N-imides in the presence of base and Cu(I) afford pyrazolo[5,1-c]-1,2,4-triazoles regioselectively. The scope of alkynes, the influence of the electronic nature of the leaving group, and variations in the 1-alkyl substituent were examined. Quantum chemical calculations were employed to explain the distinct reactivity of the propiolates.

UI MeSH Term Description Entries
D009942 Organometallic Compounds A class of compounds of the type R-M, where a C atom is joined directly to any other element except H, C, N, O, F, Cl, Br, I, or At. (Grant & Hackh's Chemical Dictionary, 5th ed) Metallo-Organic Compound,Metallo-Organic Compounds,Metalloorganic Compound,Organometallic Compound,Metalloorganic Compounds,Compound, Metallo-Organic,Compound, Metalloorganic,Compound, Organometallic,Compounds, Metallo-Organic,Compounds, Metalloorganic,Compounds, Organometallic,Metallo Organic Compound,Metallo Organic Compounds
D011720 Pyrazoles Azoles of two nitrogens at the 1,2 positions, next to each other, in contrast with IMIDAZOLES in which they are at the 1,3 positions.
D011789 Quantum Theory The theory that the radiation and absorption of energy take place in definite quantities called quanta (E) which vary in size and are defined by the equation E Quantum Theories,Theories, Quantum,Theory, Quantum
D002384 Catalysis The facilitation of a chemical reaction by material (catalyst) that is not consumed by the reaction. Catalyses
D003300 Copper A heavy metal trace element with the atomic symbol Cu, atomic number 29, and atomic weight 63.55. Copper-63,Copper 63
D013237 Stereoisomerism The phenomenon whereby compounds whose molecules have the same number and kind of atoms and the same atomic arrangement, but differ in their spatial relationships. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed) Molecular Stereochemistry,Stereoisomers,Stereochemistry, Molecular,Stereoisomer
D014230 Triazoles Heterocyclic compounds containing a five-membered ring with two carbon atoms and three nitrogen atoms with the molecular formula C2H3N3. Triazole
D015394 Molecular Structure The location of the atoms, groups or ions relative to one another in a molecule, as well as the number, type and location of covalent bonds. Structure, Molecular,Molecular Structures,Structures, Molecular

Related Publications

Davit Jishkariani, and C Dennis Hall, and Alexander A Oliferenko, and David Leino, and Alan R Katritzky
Synthesis and Evaluation of Novel [1,2,4]Triazolo[5,1-c][1,2,4]-triazines and Pyrazolo[5,1-c][1,2,4]triazines as Potential Antidiabetic Agents.
May 2017, Archiv der Pharmazie,
Davit Jishkariani, and C Dennis Hall, and Alexander A Oliferenko, and David Leino, and Alan R Katritzky
Synthesis of new pyrazolo[5,1-c][1,2,4] benzotriazines, pyrazolo[5,1-c]pyrido[4,3-e][1,2,4] triazines and their open analogues as cytotoxic agents in normoxic and hypoxic conditions.
November 2008, Bioorganic & medicinal chemistry,
Davit Jishkariani, and C Dennis Hall, and Alexander A Oliferenko, and David Leino, and Alan R Katritzky
Cu-catalyzed direct C-H bond functionalization: a regioselective protocol to 5-aryl thiazolo[3,2-b]-1,2,4-triazoles.
February 2013, Organic & biomolecular chemistry,
Davit Jishkariani, and C Dennis Hall, and Alexander A Oliferenko, and David Leino, and Alan R Katritzky
Synthesis of Pyrazolo[5,1-a]isoquinolines and 8-Methylenepyrazolo[5,1-a]isoindoles via Regioselective C-C Coupling and Alkyne Hydroamination.
November 2015, The Journal of organic chemistry,
Davit Jishkariani, and C Dennis Hall, and Alexander A Oliferenko, and David Leino, and Alan R Katritzky
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)),
Davit Jishkariani, and C Dennis Hall, and Alexander A Oliferenko, and David Leino, and Alan R Katritzky
Cu-catalyzed arylation of the amino group in the indazole ring: regioselective synthesis of pyrazolo-carbazoles.
February 2015, Organic & biomolecular chemistry,
Davit Jishkariani, and C Dennis Hall, and Alexander A Oliferenko, and David Leino, and Alan R Katritzky
Synthesis, antibacterial activity and cytotoxicity of new fused pyrazolo[1,5-a]pyrimidine and pyrazolo[5,1-c][1,2,4]triazine derivatives from new 5-aminopyrazoles.
June 2013, European journal of medicinal chemistry,
Davit Jishkariani, and C Dennis Hall, and Alexander A Oliferenko, and David Leino, and Alan R Katritzky
Rh(II)-Catalyzed Transannulation of 1,2,4-Oxadiazole Derivatives with 1-Sulfonyl-1,2,3-triazoles: Regioselective Synthesis of 5-Sulfonamidoimidazoles.
September 2018, The Journal of organic chemistry,
Davit Jishkariani, and C Dennis Hall, and Alexander A Oliferenko, and David Leino, and Alan R Katritzky
Copper-catalyzed decarboxylative regioselective synthesis of 1,5-disubstituted 1,2,3-triazoles.
March 2018, Chemical communications (Cambridge, England),
Davit Jishkariani, and C Dennis Hall, and Alexander A Oliferenko, and David Leino, and Alan R Katritzky
Regioselective synthesis of 3-trifluoromethyl 1,2,4-triazoles via photocycloaddition of sydnone with CF3CN.
November 2022, Chemical communications (Cambridge, England),
Copied contents to your clipboard!