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 2007(3): 367-374
DOI: 10.1055/s-2006-958963
DOI: 10.1055/s-2006-958963
PAPER
© Georg Thieme Verlag Stuttgart · New York
Synthesis of 8-Substituted Pyrazolo[1,5-a]-1,3,5-triazine Derivatives by Palladium-Catalyzed Cross-Coupling Reactions
Further Information
Received
5 September 2006
Publication Date:
21 December 2006 (online)
Publication History
Publication Date:
21 December 2006 (online)
Abstract
8-Substituted pyrazolo[1,5-a]-1,3,5-triazine derivatives 6 were prepared from the corresponding 8-iodopyrazolo[1,5-a]-1,3,5-triazines 5 through palladium-catalyzed cross-coupling reactions. Several bioisosteres of hypoxanthine drugs 2 were then prepared by final nucleophilic aromatic substitution.
Key words
purine - bioisosteres - pyrazolo[1,5-a]-1,3,5-triazine - palladium
- 1
Senga K.O’Brien DE.Scholten MB.Novinson T.Miller JP.Robins RK. J. Med. Chem. 1982, 25: 243 -
2a
Gilligan PJ.Folmer BK.Hartz RA.Koch S.Nanda KK.Andreuski S.Fitzgerald L.Miller K.Marshall WJ. Bioorg. Med. Chem. 2003, 11: 4093 -
2b
He L.Gilligan PJ.Zaczek R.Fitzgerald LW.McElroy J.Shen H.-SL.Saye JA.Kalin NH.Shelton S.Christ D.Trainor G.Hartig P. J. Med. Chem. 2000, 43: 449 - 3
Almansa C.de Arriba AF.Cavalcanti FL.Gómez LA.Miralles A.Merlos M.García-Rafanell J.Forn J. J. Med. Chem. 2001, 44: 350 -
4a
Prevost G,Lonchampt M.-O,Kim S,Morgan B,Ulibarri G, andThurieau C. inventors; PCT Int. Appl. WO 2002050079. Chem. Abstr. 2002, 137, 47234 -
4b
Guzi TJ, andParuch K. inventors; US Patent US 2005187219. Chem. Abstr. 2005, 143, 248417 - 5
Lübbers T.Angehrn P.Gmünder H.Herzig S.Kulhanek J. Bioorg. Med. Chem. Lett. 2000, 10: 821 - 6
Subramanyam C.Ault B.Sawutz D.Bacon ER.Singh B.Pennock PO.Kelly MD.Kraynak M.Krafte D.Treasurywala A. J. Med. Chem. 1995, 38: 587 - 7
Glasky AJ.Glasky MS.Ritzmann RF.Rathbone MP. Exp. Opin. Invest. Drugs 1997, 6: 1413 - 8
Rathbone MP.Middlemiss PJ.Crocker CE.Glasky MS.Juurlink BHJ.Ramirez JJ.Cicarelli R.Di Ioro P.Caciagli F. Exp. Opin. Invest. Drugs 1999, 8: 1255 - 9
Grundman M.Caparelli E.Kim HT.Morris JC.Farlow M.Rubin EH.Heidebrink J.Hake A.Ho G.Schultz AN.Schafer K.Houston W.Thomas R.Thal LJ. Life Sci. 2003, 73: 539 - 10
Holmes M.Maysinger D.Foerster D.Pertens E.Barlas C.Diamond J. Mol. Cell. Neurosci. 2003, 24: 568 - 11
Glasky AJ. inventors; PCT Int. Appl. WO 9957119. Chem. Abstr. 1999, 131, 322486 -
12a
Zhang H.-C.Brakta M.Daves GD. Tetrahedron Lett. 1993, 34: 1571 -
12b
Zhang H.-C.Daves GD. Organometallics 1993, 12: 1499 -
12c
Zhang H.-C.Brakta M.Daves GD. Nucleosides Nucleotides 1995, 14: 105 - 13
Raboisson P.Baurand A.Cazenave J.-P.Gachet C.Schultz D.Spiess B.Bourguignon J.-J. J. Org. Chem. 2002, 67: 8063 -
14a
Kobe J.Robins RK.O’Brien DE. J. Heterocycl. Chem. 1974, 199 -
14b
Tam SY.-K.Klein RS.Wempen I.Fox JJ. J. Org. Chem. 1979, 44: 4547 -
14c
Vogel A.Troxler F. Helv. Chim. Acta 1975, 58: 761 -
15a
Raboisson P.Schultz D.Lugnier C.Bourguignon J.-J. Tetrahedron Lett. 2002, 43: 9501 -
15b
Raboisson P.Schultz D.Lugnier C.Mathieu R.Bourguignon J.-J. Tetrahedron Lett. 2003, 44: 703 - 16
Liu Y.Li K. Macromol. Rapid Commun. 2002, 23: 739 - 17
Bernard P,Raboisson P, andJoseph B. inventors; PCT Int. Appl. WO 2004011464. Chem. Abstr. 2004, 140, 146171