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 2004(17): 2893-2899
DOI: 10.1055/s-2004-834868
DOI: 10.1055/s-2004-834868
PAPER
© Georg Thieme Verlag Stuttgart · New York
A General Approach to Selective Functionalization of 1,2,4-Triazines Using Organometallics in Palladium-Catalyzed Cross-Coupling and Addition Reactions
Further Information
Received
8 February 2004
Publication Date:
15 October 2004 (online)
Publication History
Publication Date:
15 October 2004 (online)

Abstract
A selective way to obtain disubstituted 1,2,4-triazines in good yields by combining addition reactions and palladium-catalyzed cross-coupling reactions of organometallics with 3-methylsulfanyl-1,2,4-triazine is described.
Key words
1,2,4-triazines - palladium - cross-coupling - selective addition - organometallics - catalysis
- 1
Lacefield WB. inventors; US Patent, US 3948894. ; Chem. Abstr. 1974, 85, 33089 -
2a
Neunhoeffer H. In Chemistry of Heterocyclic Compounds Vol. 33:Weissberger A.Taylor EC. J. Wiley Interscience; New York: 1978. p.189 -
2b
Konno S.Osawa N.Yamanaka H. J. Agric. Food Chem. 1995, 43: 838 - 3
Gschneidner KA.Eyring L.Choppin GR.Lander GH. Handbook on the Physics and Chemistry of Rare Earths Vol. 18:Gschneidner KA.Eyring L. Elsevier; New York: 1994. p.197-238 -
4a
Neunhoeffer H. In Comprehensive Heterocyclic Chemistry II Vol. 6:Katrizky AR.Rees CW.Scriven EFV. Pergamon Press; Oxford: 1996. p.507 -
4b
Zhao Z.Leister WH.Strauss KA.Wisnoski DD.Lindsley CW. Tetrahedron Lett. 2003, 44: 1123 -
5a
Limanto J.Desmond RA.Gauthier DR.Devine PN.Reamer RA.Volante RP. Org. Lett. 2003, 5: 2271 -
5b
Ohsumi T.Neunhoffer H. Tetrahedron 1992, 48: 651 -
5c
Taylor EC.French LG. J. Org. Chem. 1989, 54: 1245 -
6a
Charushin VN.Alexeev SG.Chupakhin ON. Adv. Heterocycl. Chem. 1989, 46: 73 ; and references cited therein -
6b
Rykowski A.Makoska M. Liebigs Ann. Chem. 1988, 627 -
6c
Rykowski A.Olender E.Branowska D.van der Plas HC. Org. Prep. Proced. Int. 2001, 33: 501-514 -
6d
Szczepkowska-Sztolcman J.Katrusiak A.Wojtowicz-Rajchel H.Golankiewicz K. J. Chem. Soc., Perkin Trans. 1 2002, 2549 ; and references cited therein -
6e
Branowska D.Ostrowski S.Rykowski A. Chem. Pharm. Bull. 2002, 50: 463 - 7
Konno S.Sagi M.Yoshiba N.Yamanaka H. Heterocycles 1987, 26: 3111 - 8
Paudler WW.Chem IK. J. Heterocycl. Chem. 1970, 7: 767 - 9
Pridgen LN.Killmer LB.Lee Webb R. J. Org. Chem. 1982, 47: 1985 -
10a
Pridgen LN.Jones SS. J. Org. Chem. 1982, 47: 1590 -
10b
Alvarez-Ibarra C.Asperilla R.de Dios-Corredor C.Martinez-Santos E.Luz Quiroga M. Heterocycles 1991, 32: 2127 - 11
Liebeskind LS.Srogl J. J. Am. Chem. Soc. 2000, 122: 11260 -
12a
Savarin C.Srogl J.Liebeskind LS. Org. Lett. 2001, 3: 91 -
12b
Savarin C.Liebeskind LS. Org. Lett. 2001, 3: 2149 - 13
Alphonse F.-A.Suzenet F.Keromnes A.Lebret B.Guillaumet G. Synlett 2002, 447 -
14a
Pereyre M.Quintard J.-P.Rahm A. Tin in Organic Synthesis Butterworth; London: 1987. -
14b
Lee AS.-Y.Dai W.-C. Tetrahedron 1997, 53: 859 ; and references therein -
14c
Smith ND.Mancuso J.Lautens M. Chem. Rev. 2000, 100: 3257 - 15
Alphonse F.-A.Suzenet F.Keromnes A.Lebret B.Guillaumet G. Org. Lett. 2003, 5: 803 - 16
Metal-catalysed Cross-coupling Reactions
Diederich F.Stang PJ. Wiley-VCH; Weinheim: 1998. -
17a
Gros P.Fort Y. Synthesis 1999, 754 -
17b
Fang Y.-Q.Hanan GS. Synlett 2003, 852 -
17c
Sakamoto T.Kondo Y.Murata N.Yamanaka H. Tetrahedron Lett. 1992, 33: 5373 - 18
Knochel P.Almena Perea JJ.Jones P. Tetrahedron 1998, 54: 8275 - 19
Angiolelli ME.Casalnuovo AL.Selby TP. Synlett 2000, 905 - 20
Heilman WP.Heilman RD.Scozzie JA.Wayner RJ.Gullo JM.Ariyan ZS. J. Pharm. Sci. 1980, 69: 282 - 21
Taylor EC.Pont JL.Warner JC. Tetrahedron 1987, 43: 5159