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Cu-catalyzed aerobic oxidative cyclization of guanidylpyridines and derivatives. 2015

Björn Bartels, and Conor Gordon Bolas, and Philipp Cueni, and Serena Fantasia, and Nicolas Gaeng, and Andrada Stefania Trita
Roche Pharmaceutical Research and Early Development, Roche Innovation Center Basel, preclinical CMC, Process Research, F. Hoffmann-La Roche Ltd. , Grenzacherstrasse 124, 4070 Basel, Switzerland.

A new method for the straightforward synthesis of 2-amino-[1,2,4]triazolo[1,5-a]pyridines and derivatives is presented. The target products are synthesized in high yields from guanidylpyridines and analogues via copper-catalyzed N-N coupling. The present methodology shows a wide scope, tolerating not only different substituents on the pyridine ring but also different heterocylic rings such as pyrazines, pyrimidines, and pyridazines.

UI MeSH Term Description Entries
D010084 Oxidation-Reduction A chemical reaction in which an electron is transferred from one molecule to another. The electron-donating molecule is the reducing agent or reductant; the electron-accepting molecule is the oxidizing agent or oxidant. Reducing and oxidizing agents function as conjugate reductant-oxidant pairs or redox pairs (Lehninger, Principles of Biochemistry, 1982, p471). Redox,Oxidation Reduction
D011725 Pyridines Compounds with a six membered aromatic ring containing NITROGEN. The saturated version is PIPERIDINES.
D011743 Pyrimidines A family of 6-membered heterocyclic compounds occurring in nature in a wide variety of forms. They include several nucleic acid constituents (CYTOSINE; THYMINE; and URACIL) and form the basic structure of the barbiturates.
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
D003500 Cyclization Changing an open-chain hydrocarbon to a closed ring. (McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed) Cyclizations
D014230 Triazoles Heterocyclic compounds containing a five-membered ring with two carbon atoms and three nitrogen atoms with the molecular formula C2H3N3. Triazole
D019791 Guanidine A strong organic base existing primarily as guanidium ions at physiological pH. It is found in the urine as a normal product of protein metabolism. It is also used in laboratory research as a protein denaturant. (From Martindale, the Extra Pharmacopoeia, 30th ed and Merck Index, 12th ed) It is also used in the treatment of myasthenia and as a fluorescent probe in HPLC. Guanidine Hydrochloride,Guanidinium,Guanidinium Chloride,Guanidine Monohydrate,Guanidine Monohydrobromide,Guanidine Monohydrochloride,Guanidine Monohydroiodine,Guanidine Nitrate,Guanidine Phosphate,Guanidine Sulfate,Guanidine Sulfate (1:1),Guanidine Sulfate (2:1),Guanidine Sulfite (1:1),Guanidium Chloride,Chloride, Guanidinium,Chloride, Guanidium,Hydrochloride, Guanidine,Monohydrate, Guanidine,Monohydrobromide, Guanidine,Monohydrochloride, Guanidine,Monohydroiodine, Guanidine,Nitrate, Guanidine,Phosphate, Guanidine,Sulfate, Guanidine

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