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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 39, 2009 - Issue 14
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Original Articles

Alternative Approach to 1,2,4-Triazole-3-carboxamides

Pages 2585-2595 | Received 20 Aug 2008, Published online: 16 Jun 2009

REFERENCES

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  • For some typical recent examples, see Gentile , G. ; Di Fabio , R. ; Pavone , F. ; Sabbatini , F. M. ; St-Denis , Y. ; Zampori , M. G. ; Vitulli , G. ; Worby , A. Novel substituted tetrahydrotriazaacenaphthylene derivatives as potent CRF1 receptor antagonists . Bioorg. Med. Chem. Lett. 2007 , 17 , 5218 – 5221 ; Montgomery , C. P. ; Parker , D. ; Lamarque , L. Effective and efficient sensitisation of terbium luminescence at 355 nm with cell permeable pyrazolyl-1-azaxanthone macrocyclic complexes . Chem. Commun. 2007 , 37 , 3841 – 3843 ; Zimmermann , P. J. ; Buhr , W. ; Brehm , C. ; Palmer , A. M. ; Feth , M. P. ; Senn-Bilfinger , J. ; Simon , W.-A. Novel indanyl-substituted imidazo[1,2-a]pyridines as potent reversible inhibitors of the gastricH+/K+-ATPase . Bioorg. Med. Chem. Lett. 2007 , 17 , 5374 – 5378 ; Han , X. ; Civiello , R. ; Pin , S. S. ; Burris , K. ; Balanda , L. A. ; Knipe , J. ; Ren , S. ; Fiedler , T. ; Browman , K. E. ; Macci , R. ; Taber , M. T. ; Zhang , J. ; Dubowchik , G. M. An orally active corticotropin releasing factor 1 receptor antagonist from 8-aryl-1,3a,7,8-tetraaza-cyclopenta[a]indenes . Bioorg. Med. Chem. Lett. 2007 , 17 , 2026 – 2030 ; Hu , L.-Y. ; Lei , H. J. ; Du , D. ; Johnson , T. R. ; Fedij , V. ; Kostlan , C. ; Yue , W. S. ; Lovdahl , M. ; Li , J. J. ; Carroll , M. ; Dettling , D. ; Asbill , J. ; Fan , C. ; Wade , K. ; Pocalyko , D. ; Lapham , K. ; Yalamanchili , R. ; Samas , B. ; Vrieze , D. ; Ciotti , S. ; Krieger-Burke , T. ; Sliskovic , D. ; Welgus , H. Synthesis and biological evaluation of amino-pyridines as androgen receptor antagonists for stimulating hair growth and reducing sebum production . Bioorg. Med. Chem. Lett. 2007 , 17 , 5693 – 5697 ; Watterson , S. H. ; Chen , P. ; Zhao , Y. ; Gu , H. H. ; Murali Dhar , T. G. ; Xiao , Z. ; Ballentine , S. K. ; Shen , Z. ; Fleener , C. A. ; Rouleau , K. A. ; Obermeier , M. ; Yang , Z. ; McIntyre , K. W. ; Shuster , D. J. ; Witmer , M. ; Dambach , D. ; Chao , S. ; Mathur , A. ; Chen , B.-C .; Barrish , J. C. ; Robl , J. A. ; Townsend , R. ; Iwanowicz . Acridone-based inhibitors of inosine 5′–monophosphate dehydrogenase: Discovery and SAR leading to the identification of N-(2-(6-(4-ethylpiperazin-1-yl)pyridine-3-yl)propan-2-yl)-2-fluoro-9-oxo-9,10-dihydroacridine-3-carboxamide (BMS-566419) . J. Med. Chem. 2007 , 50 , 3730 – 3742 .
  • Kreutzberger , A. J. Reactions of trichloromethyl-1,3,5-triazine derivatives with amines. J. Am. Chem. Soc. 1957, 79, 2629–2633; Kober , E. J. Conversion of trichloromethyl groups into dichloromethyl groups. J. Org. Chem. 1961, 26, 2270–2271; Elnagdi , M. H. ; Fahmy , S. M. ; Hafez , E. A. A. ; Elmoghayar , M. R. H. ; Amer , S. A. R. Pyrimidine derivatives and related compounds: A novel synthesis of pyrimidines, pyrazolo[4,3-d]pyrimidines, and isoxazolo[4,3-d]pyrimidines. J. Heterocycl. Chem. 1979, 16, 1109–1111; Elnagdi , M. H. ; Elfahham , H. A. ; Ghozlan , S. A. S. ; Elgemeie , G. E. H. Activated nitriles in heterocyclic synthesis: A new procedure for the synthesis of pyrimidine derivatives. J. Chem. Soc., Perkin Trans. 1 1982, 11, 2667–2670; Mencarelli , P. ; Mattioli , M. Reactions of 4-(trihalomethyl)quinazolines with aliphatic amines: Role of the halogen atom and of the amine on the reaction pattern. J. Org. Chem. 1990, 55, 776–778; Mylari , B. L. ; Oates , P. J. ; Zembrowski , W. J. ; Beebe , D. A. ; Conn , E. L. ; Linhares , J. C. ; Withbroe , G. J. A sorbitol dehydrogenase inhibitor of exceptional in vivo potency with a long duration of action: 1-R-{4-[4-(4,6-Dimethyl[1,3,5]triazin-2-yl)-2R,6S-dimethylpiperazin-1-yl]pyrimidin-2-yl}ethanol. J. Med. Chem. 2002, 45, 4398–4401; Werbel , L. M. ; Elslager , E. F. ; Hess , C. ; Hutt , M. P. Antimalarial activity of 2-(substituted amino)-4,6-bis(trichloromethyl)1,3,5triazines and N-(chlorophenyl)-N′-[4-(substituted amino)-6-(trichloromethyl)-1,3,5-triazin-2-yl]guanidines. J. Med. Chem. 1987, 30, 1943–1948.
  • For a typical example, see Le Fave , G. M. ; Scheurer , P. G. Some reactions of the trifluoromethyl group in the benzotrifluoride series, II: Alcoholysis . J. Am. Chem. Soc. 1950 , 72 , 2464 – 2465 .
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