Synthesis, Table of Contents PAPER © Georg Thieme Verlag Stuttgart · New York The Synthesis of 1,2,3-Triazoles from Nitroalkenes - Revisited Béatrice Quiclet-Sire*, Samir Z. Zard*Laboratoire de Synthèse Organique associé au CNRS Ecole Polytechnique, 91128 Palaiseau, FranceFax: +33(1)69333851; e-Mail: zard@poly.polytechnique.fr; Recommend Article Abstract Buy Article All articles of this category Abstract Nitroalkenes or vicinal acetoxy nitro derivatives undergo a clean reaction with sodium azide in hot dimethyl sulfoxide to give the corresponding 1,2,3-triazoles in good yield. Key words azides - cyclisations - heterocycles - nitroalkenes - 1,2,3-triazoles Full Text References References 1 Zefirov NS. Chapovskaya NK. Kolesnikov VV. J. Chem. Soc. D 1971, 1001 For the synthesis of 1,2,3-triazoles by cycloaddition of organic azides to nitroalkenes, see: 2a Piet J.-C. Le Hetet G. Cailleux P. Benhaoua H. Carrié R. Bull. Soc. Chim. Belg. 1996, 105: 33 2b Cailleux P. Piet J.-C. Benhaoua H. Carrié R. Bull. Soc. Chim. Belg. 1996, 105: 45 Very recently, the cycloaddition of trimethylsilyl azide with aromatic nitroacrylates and nitroacrylonitriles has been reported, see: 2c Amantini D. Fringuelli F. Piermatti O. Pizzo F. Zunino E. Vaccaro L. J. Org. Chem. 2005, 70: 6526 The reaction of sodium azide with vinyl sulfones was found to give 1,2,3-triazoles, see: 2d Beck G. Günther D. Chem. Ber. 1973, 106: 2758 3a Ono N. The Nitro Group in Organic Synthesis Wiley-VCH; New York: 2001. 3b Ballini R. Bosica G. Fiorini D. Palmieri A. Petrini M. Chem. Rev. 2005, 105: 933 3c Rosini G. Ballini R. Synthesis 1988, 833 3d Seebach D. Colvin EW. Lehr F. Weller T. Chimia 1979, 33: 1 4 Surprisingly, a search of Beilstein revealed only one example of a 1,2,3-triazole with a hydroxymethyl side chain on the carbon: Vereshchagin L. I.; Tikhonova L. G., Maksikova A. V., Gavrilov L. D., Gareev G. A.; Zh. Org. Khim.; 1979, 15: 612 5a Rostovstev VV. Green LG. Fokin VV. Sharpless KB. Angew. Chem. Int. Ed. 2002, 41: 2596 5b Tornøe CW. Christensen C. Meldal M. J. Org. Chem. 2002, 67: 3057 5c Kolb HC. Finn MG. Sharpless KB. Angew. Chem. Int. Ed. 2001, 40: 2004 5d Kolb HC. Sharpless KB. Drug Discov. Today 2003, 8: 1128 1,2,3-Triazoles have been found to possess muscarinic anticonvulsant anti-HIV and β-lactamase inhibitory activities. Some act as anticoccidiostats, see: 6a Bochis RJ. Chabala JC. Harris E. Peterson LH. Barash L. Beattie T. Brown JE. Graham DW. Waksmunski FS. Tischler M. Joshua H. Smith J. Colwell LF. Wyvratt MJ. Fisher MH. Tamas T. Nicolich S. Schleim KD. Wilks G. Olson G. J. Med. Chem. 1991, 34: 2843 6b Willner D. Jelenevsky AM. Cheney LC. J. Med. Chem. 1972, 15: 948 6c Micetich RG. Maiti SN. Spevak P. Hall TW. Yamabe S. Ishida N. Tanaka M. Yamazaki T. Nakai A. Ogawa K. J. Med. Chem. 1987, 30: 1469 6d Hlasta DJ. Ackerman JH. J. Org. Chem. 1994, 59: 6184 6e Alvarez R. Velazquez S. San-Felix A. Aquaro S. De Clercq E. Perno C.-F. Karlsson A. Balzarini J. Camarasa MJ. J. Med. Chem. 1994, 37: 4185 6f Kelley JL. Koble CS. Davis RG. McLean EW. Soroko FE. Cooper BR. J. Med. Chem. 1995, 38: 4131 6g Moltzen EK. Pedersen H. Boegesoe KP. Meier E. Frederiksen K. Sanchez C. Lemboel HL. J. Med. Chem. 1994, 37: 4085 7 Kallander LS. Lu Q. Chen W. Tomaszek T. Yang G. Tew D. Meek TD. Hofmann GA. Schulz-Pritchard CK. Smith WW. Janson CC. Ryan MD. Zhang G.-F. Johanson KO. Kirkpatrick RB. Ho TF. Fisher PW. Mattern MR. Johnson RK. Hansbury MJ. Winkler JD. Ward KW. Veber DF. Thompson SK. J. Med. Chem. 2005, 48: 5644 8 Bourguignon J. Le Nard G. Quéguiner G. Can. J. Chem. 1985, 63: 2354 9 Wessling M. Schaefer HJ. Chem. Ber. 1991, 124: 2303 10 Barton DHR. Motherwell WB. Simon ES. Zard SZ. J. Chem. Soc., Perkin Trans. 1 1986, 2243 11 Frost DA. Morrison GA. J. Chem. Soc., Perkin Trans. 1 1973, 2388 12 Ouvry G. Quiclet-Sire B. Zard SZ. Org. Lett. 2003, 5: 2907 13 Shih NY. Lupo AT. Aslanian R. Orlando S. Piwinski JJ. Green MJ. Ganguly AK. Clark MA. Tozzi S. Kreutner W. Hey JA. J. Med. Chem. 1995, 38: 1593 14 Barton DHR. Kervagoret J. Zard SZ. Tetrahedron 1990, 46: 7587 15 Tokunaga Y. Ihara M. Fukumoto K. J. Chem. Soc., Perkin Trans. 1 1997, 207 16a Barton DHR. Motherwell WB. Zard SZ. J. Chem. Soc., Chem. Commun. 1982, 551 16b Barton DHR. Motherwell WB. Zard SZ. Bull. Soc. Chim. Fr. 1983, II: 61 17 Bordwell FG. Bartmess JE. J. Org. Chem. 1978, 43: 3101 18 Fusco R. Bianchetti G. Pocar D. Gazz. Chim. Ital. 1961, 91: 933 19a Buckler RT. Hartzler HE. Kurchacova E. Nichols G. Phillips BM. J. Med. Chem. 1978, 21: 1254 19b Moltzen EK. Pedersen H. Boegesoe KP. Meier E. Frederiksen K. Sanchez C. Lembol HL. J. Med. Chem. 1994, 37: 4085