Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2008(1): 149-154
DOI: 10.1055/s-2007-983896
DOI: 10.1055/s-2007-983896
PSP
© Georg Thieme Verlag Stuttgart · New York
A Simplified Approach to N- and N,N′-Linked 1,2,4-Triazoles by Transamination
Further Information
Received
15 March 2007
Publication Date:
11 September 2007 (online)
Publication History
Publication Date:
11 September 2007 (online)
Abstract
A facile one-step procedure for the preparation of 4,4′-bis-1,2,4-triazole is reported. Direct transamination of N,N-dimethylformamide azine dihydrochloride by heating with 4-amino-1,2,4-triazole in refluxing benzene readily yields the target molecule in short duration of time with significant yield (73%). This catalyst-free method was extended to synthesise a series of 4-substituted 1,2,4-triazoles of potential interest in coordination chemistry.
Key words
amines - amino acids - ligands - transamination - 4,4′-bis-1,2,4-triazole
-
1a
Kane JM.Baron BM.Dudley MW.Soressen SM.Staeger MA.Miller FP. J. Med. Chem. 1990, 33: 2772 -
1b
Menegola E.Broccia ML.Di Renzo F.Giavini E. Reprod. Toxicol. 2006, 22: 186 -
1c
Chollet JF.Bonnemain JL.Miginiac L.Rohr O. J. Pestic. Sci. 1990, 29: 427 -
1d
Holla BS.Veerendra B.Shivananda MK.Poojary B. Eur. J. Med. Chem. 2003, 38: 759 - 2
Meister RT. Chemical Handbooks ’92 Meister Publishing Company; Willoughby OH / USA: 1992. - 3
Bayer HO,Cook RS, andvon Meyer WC. inventors; US Patent 382137628. ; Chem. Abstr. 1972, 76, 113224 - 4
Seidel L,von Meyer WC, andGreenfield S. inventors; US Patent 4120684. ; Chem. Abstr. 1979, 90, 54948 - 5
Sivabalan R.Anniyappan M.Pawar SJ.Talawar MB.Gore GM.Venugopalan S.Gandhe BR. J. Hazard. Mater. 2006, 137: 672 -
6a
Bentiss F.Bouanis M.Mernari B.Traisnel M.Vezin H.Lagrenee M. Appl. Surf. Sci. 2007, 235: 3696 -
6b
House GL.Levy DH.Yang X.Slusarek W. J. Imaging Sci. Technol. 2005, 49: 398 - 7
Laus G.Kloetzer W. Synthesis 1989, 269 -
8a
Haasnoot JG. In Magnetism: A Supramolecular FunctionKahn O. Kluwer Academic Publishers; Dordrecht: 1996. p.299 -
8b
Haasnoot JG. Coord. Chem. Rev. 2000, 200/202: 131 - 9
Garcia Y.Niel V.Muñoz MC.Real JA. Top. Curr. Chem. 2004, 233: 229 - 10
Ouellette W.Galán-Mascarós JR.Dunbar KR.Zubieta J. Inorg. Chem. 2006, 45: 1909 - 11
Lees AC.Evrard B.Keyes TE.Vos JG.Kleverlaan CJ.Alebbi M.Bignozzi CA. Eur. J. Inorg. Chem. 1999, 2309 - 12
Zhang J.-P.Lin YY.Zhang W.-X.Chen X.-M. J. Am. Chem. Soc. 2005, 127: 14162 - 13
Bartlett RK.Humphrey IR. J. Chem. Soc. C 1967, 1664 - 14
Haasnoot JG.Groeneveld WL. Z. Naturforsch., B: Anorg. Chem. Org. Chem. 1979, 34: 1500 - 15
Katritzky AR.Suwinski JW. Tetrahedron 1975, 31: 1549 -
16a
de Mendoza J.Castellanos ML.Fayet J.-P.Vertut MC.Elguero J. J. Chem. Res., Synop. 1980, 50 -
16b
Curtis ADM. In Science of Synthesis Vol. 13:Storr R.Gilchrist T. Thieme; Stuttgart: 2004. p.603 -
17a
Castellanos ML.Llinas M.Bruix M.de Mendoza J.Martin MR. J. Chem. Soc., Perkin Trans. 1 1985, 1209 -
17b
Woisel P.Cazier F.Surpateanua G.Baudel V.Boursier V. Heterocycl. Commun. 2002, 8: 71 -
18a
Sternfeld F.Guiblin AR.Jelley RA.Matassa VG.Reeve AJ.Hunt PA.Beer MS.Held A.Stanton JA.Sohal B.Watt AP.Street LJ. J. Med. Chem. 1999, 42: 677 -
18b
Bouchet P.Coquelet C. J. Chem. Soc., Perkin Trans. 2 1974, 449 - 19
Bosshard HH.Mory R.Schmid M.Zollinger H. Helv. Chim. Acta 1959, 42: 1653 -
20a
Boland Y.Attout A.Marchand-Bryanert J.Garcia Y. J. Chromatogr., A 2007, 1141: 145 -
20b
Boland Y.Hertsens P.Marchand-Bryanert J.Garcia Y. Synthesis 2006, 1504 - 21
Fohlisch B.Braun R.Schultze KW. Angew. Chem., Int. Ed. Engl. 1967, 6: 361 -
22a
Garcia Y.Kahn O.Rabardel L.Chansou B.Tuchagues J.-P. Inorg. Chem. 1999, 38: 4663 -
22b
Garcia Y.van Koningsbruggen PJ.Kooijman H.Spek AL.Haasnoot JG.Kahn O. Eur. J. Inorg. Chem. 2000, 307 -
22c
Garcia Y.van Koningsbruggen PJ.Kooijman H.Spek AL.Haasnoot JG.Kahn O. Eur. J. Inorg. Chem. 2000, 575 - 23
Sternfeld F.Baker R.Broughton HB.Guiblin AR.Jelley RA.Matassa VG.Reeve AJ.Beer MS.Stanton JA.Hargreaves RJ.Shepheard SL.Longmore J.Razzaque Z.Graham MI.Sohal B.Street LJ. Bioorg. Med. Chem. Lett. 1996, 6: 1825 - 24
Zou R.-Q.Cai L.-Z.Guo G.-C. J. Mol. Struct. 2005, 737: 125 - 25
Mozolis V.Rastenyte L.Gurkliene M. Chemija 1987, 4: 50 ; Chem. Abstr. 1998, 109, 6465 - 26
Wiley RH.Hart AJ. J. Org. Chem. 1953, 18: 1368 - 27
Cai H.Hu H.-M.Chen W.-Z.Xu Y.You X.-Z. Acta Crystallogr., C: Cryst. Struct. Commun. 1999, 55: IUC9900082 -
28a
Potewar TM.Siddiqui SA.Lahoti RJ.Srinivasan KV. Tetrahedron Lett. 2007, 48: 1721 -
28b
Siddiqui SA.Potewar TM.Lahoti RJ.Srinivasan KV. Synthesis 2006, 2849 -
28c
Siddiqui SA. Synlett 2006, 155 - 29
Martin JC.Barton KR.Gott PG.Mean RH. J. Org. Chem. 1966, 31: 943