A New Protocol for The Synthesis of 5-(azidomethyl)-4-phenyl-1H- 1,2,3-triazole From Baylis-Hillman Adducts Derived from Nitro Olefins.
Abstract
The Baylis-Hillman adducts derived from nitroolefins have been conveniently
transformed into 5-(azidomethyl)-4-phenyl-1h-1,2,3-triazole via simple reaction condition. These compounds have been demonstrated for the synthesis of azidomethyl is highly biological reactive compounds. This novel bromo derivative of the BH adduct was simply treated with mole percentage of sodium azide in reactive condition. As a result, these novel azidomethyl
compounds were extremely encouraging and provided fresh chances for building libraries of several new molecules. For the effective synthesis of N-unsubstituted 1,2,3-triazoles, a new one- pot, three-component reaction was created using the Julia reagent, aldehyde, and sodium azide. A wide range of substrates, including Julia reagents and aldehydes, may be utilised in this
reaction system to generate a modest library of title compounds. The reactions could've been done out that under mild reaction conditions without any care.
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Basavaiah, D. Venkateswara Rao, K. Reddy R. J. Chem. Soc. Rev. 2007;36.1581–1588.
Basavaiah D. Rao A. J. Satyanarayana T. Chem. Rev. 2003; 103. 811–891.
Ciganek E. Organic Reactions L. A. Paquette (Ed.) Wiley: New York, 1997; vol. 51, pp. 201–350.
Aroyan C.E.Vasbinder M.M. Miller S.J. Org. Lett. 2005; 7 3849–3851; (b) Kabalka, G. W.Dong, G.; Venkataiah, B.J. Org. Chem. 2005;70, 9207–9210;
Basavaiah, D.Aravindu K. Org. Lett. 2007; 9.2453–2456;
Rostovtsev V.V. Green L.G. Fokin V.V.K. Barry Sharpless, B.K. Angew. Chem. Int. Ed. 2002; 41. 2596
Wu, P. Feldman, A.K. Nugent A.K. Hawker C.J.; Scheel, A.; Voit, B.; Pyun, J; Fre´chet, J.M.J.; Sharpless, K.B.; Fokin, V.V. Angew. Chem. Int. Ed. 2004, 43, 3928;
Bourne, Y.; Kolb, H.C.; Radic, Z.; Sharpless, K.B.; Taylor, P.; Marchot, P. Proc.Natl.Acad.Sci. U.S.A. 2004, 101, 1449.
Bodine, D.K.; Gin D.Y. Gin, M.S.J. Am. Chem. Soc. 2004, 126, 1638
Fazio, F.; Bryan, M.C.; Blixt, O.; Paulson, J.C.; Wong, C.H.J. Am. Chem. Soc. 2002, 124, 14397.
Alvarez, R.; Velaquez, S.; Felix, A.S.; Aquaro, S.; Declercq, E.; Perno, C.F.; Karlsson, A.; Balzarini, J.; Camarasa, M.J.J. Med. Chem. 1994, 37, 4185.
Buckle, D.R.; Rockell, C.J.M.; Smith, H.; Spicer, B.A.J. Med. Chem. 1986, 29, 2262;
Sugawara, A.; Sunazuka, T.; Hirose, T.; Nagai, K.; Yamaguchi, Y.; Hanaki, H.; Sharpless, K.B.;
Omura, S. Bioorg. Med. Chem. Lett. 2007, 17, 6340.
Yang, J.; Hoffmeister, D.; Liu, L.; Fu, X.; Thorson, J.S. Bioorg. Med. Chem. 2004, 12, 1577;
Rheingold, A.L.; Liable-Sands, L.M.; Trofimenko, S. Angew. Chem., Int. Ed. 2000, 39, 3321.
Morgan, N.H. (Chomerics) Eur. Pat. Appl. EP 437979A2 19910724, 1991.
Brawn, R.A.; Welzel, M.; Lowe, J.T.; Panek, J, S. Org. Lett. 2010, 12, 336.
Hotha, S.; Anegundi, R.I.; Natu, A.A. Tetrahedron Lett. 2005, 46, 4585.
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