Synthesis of 1-(R-Phenyl)-5-(R-Methyl)-1H-1,2,3-triazole-4-carboxylic acids by one-pot tandem reaction

Synthetic Communications

Volumn 40, Issue 13, 2010, Pages 1932-1938

  Pokhodylo, Nazariy T ^a   Matiychuk, Vasyl S ^a   Obushak, Mykola D ^a  

^a IVAN FRANKO NATIONAL UNIVERSITY OF LVIV   (Ukraine)

Author keywords

1H 1,2,3 triazoles; Azides; Cyclocondensation; Multicomponent reactions

Indexed keywords

1H 1,2,3 TRIAZOLE 4 CARBOXYLIC ACID; AZIDE; BENZENE DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; CHLORINE; NUCLEOPHILE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHEMICAL BOND; CHEMICAL STRUCTURE; MOLECULE; NUCLEOPHILICITY; ONE POT SYNTHESIS; OXIDATION; REACTION OPTIMIZATION;

EID: 77953455727     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910903174408     Document Type: Article

References (10)

1. Dömling, A. Recent developments in isocyanide-based multicomponent reactions in applied chemistry. Chem. Rev. 2006, 106, 17-89.
2. Zhu, J.; Bienaymé, H. (Eds.). Multicomponent Reactions; Wiley-VCH: Weinheim, 2005.
3. Rodriquez, M.; Taddei, M. Synthesis of heterocycles via microwave-assisted cycloadditions and cyclocondensations. Top. Heterocycl. Chem. 2006, 213-266.
4. Krivopalov, V. P.; Shkurko, O. P. 1,2,3-Triazole and its derivatives: Development of methods for the formation of the triazole ring. Russ. Chem. Rev. 2005, 74, 339-379.
5. Katritzky, A. R.; Zhang, Y.; Singh, S. K. 1,2,3-Triazole formation under mild conditions via 1,3-dipolar cycloaddition of acetylenes with azides. Heterocycles. 2003, 60, 1225-1239.
6. Gil, M. V.; Arévalo, M. J.; López, O. Click chemistry: What's in a name? Triazole synthesis and beyond. Synthesis 2007, 1589-1620.
7. Olesen, P. H.; Sørensen, A. R.; Ursø, B.; Kurtzhals, P.; Bowler, A. N.; Ehrbar, U.; Hansen, B. F. Synthesis and in vitro characterization of 1-(4-aminofurazan-3-yl)-5-dialkylamino-methyl-1H-[1,2,3]triazole-4- carboxylic acid derivatives: A new class of selective GSK-3 inhibitors. J. Med. Chem. 2003, 46, 3333-3341.
8. (a) Schreiber, R. S. (Ed.). Organic Syntheses; Wiley: New York, 1951; vol.31, p. 14;
9. (b) Mustill, R. A.; Rees, A. H. Approaches to azepines: A new azepine by the photolysis of dimethyl p-azidosalicylate. J. Org. Chem. 1983, 48, 5041-5043;
10. (c) Purvis, R.; Smalley, R. K.; Suschitzky, H.; Alkhader, M. A. 3H-Azepines and related systems, II: The photolyses of aryl azides bearing electron-withdrawing substituents. J. Chem. Soc. Perkin Trans. 1 1984, 249-254.