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 2005(1): 131-135
DOI: 10.1055/s-2004-834923
DOI: 10.1055/s-2004-834923
PAPER
© Georg Thieme Verlag Stuttgart · New York
ω-Functionalized 3-Alkynylpyrazolo[1, 5-a]pyrimidines by Sonogashira Coupling
Further Information
Received
7 July 2004
Publication Date:
17 November 2004 (online)
Publication History
Publication Date:
17 November 2004 (online)
Abstract
ω-Functionalized 3-alkynylpyrazolo[1,5-a]pyrimidines were synthesized via the Pd-C/CuI/PPh3-catalyzed Sonogashira coupling of 3-iodopyrazolo[1,5-a]pyrimidines with propargylic and homopropargylic compounds. Subsequent Pd-C-catalyzed hydrogenation of the C-C triple bond afforded 3-(3-dimethylaminopropyl)-pyrazolo[1,5-a]pyrimidines.
Keywords
heterocycles - alkynes - cross-coupling - palladium - hydrogenation
- 1
Novinson T.Bhooshan B.Okabe T.Revankar GR.Wilson HR. J. Med. Chem. 1976, 19: 512 - 2
Senga K.Novinson T.Wilson HR. J. Med. Chem. 1981, 24: 610 - 3
Suzuki M.Iwasaki H.Fujikawa Y.Sakashita M.Kitahara M.Sakoda R. Bioorg. Med. Chem. Lett. 2001, 11: 1285 - 4
Almansa C.Arriba AF.Cavalcanti FL.Gomez LA.Miralles A.Forn J. J. Med. Chem. 2001, 44: 350 - 5
Fraley ME.Rubino RS.Hoffman WF.Hambaugh SR.Thomas KA. Bioorg. Med. Chem. Lett. 2002, 12: 3537 - 6
Novinson T.Hanson R.Dimmitt MK.Simmon LN.Robins RK.O’Brien DE. J. Med. Chem. 1974, 17: 645 - 7
Selleri S.Bruni F.Costagli C.Costanzo A.Guerrini G.Ciciani G.Costa B.Martini C. Bioorg. Med. Chem. 2001, 9: 2661 - 8
Kirkpatrick WE.Okabe T.Hillyard IW.Robin RK.Dren AT. J. Med. Chem. 1977, 20: 386 - 9
Calderwood DJ.Johnson DN.Munschauer R.Rafferty P. Bioorg. Med. Chem. Lett. 2002, 12: 1683 - 10
Karanik M.Pätzel M.Liebscher J. Synthesis 2003, 1201 - 11
Yin LX.Liebscher J. Synthesis 2004, 2329 -
12a
Sonogashira K.Tohda Y.Hagihara N. Tetrahedron Lett. 1975, 16: 4467 -
12b
Sonogashira K. J. Organomet. Chem. 2002, 653: 46 -
12c
Alami M.Ferri F.Linstrumelle G. Tetrahedron Lett. 1993, 34: 6403 -
12d
Negishi E.Anastasia L. Chem. Rev. 2003, 103: 1979 -
12e
Sakomoto T.Shiga F.Yasuhara A.Yamanaka H. Synthesis 1992, 746 -
13a
Li JJ.Gribble GW. Palladium in Heterocyclic Chemistry Pergamon Press; Oxford: 2000. -
13b
Kalinin VN. Synthesis 1991, 413 -
13c
Edo K.Yamanaka H.Sakamoto T. Heterocycles 1978, 9: 271 -
13d
Mcguigan C.Yarnold CJ.Jones G.Balzarini J. J. Med. Chem. 1999, 42: 4479 -
13e
Turner SC.Esbenshade TA.Bennani YL.Hancock AA. Bioorg. Med. Chem. Lett. 2003, 12: 1683 -
13f
Arnautu A.Collot V.Ros JC.Witulski B. Tetrahedron Lett. 2002, 43: 2695 -
13g
Kim JT.Gevorgyan V. Org. Lett. 2002, 4: 4697 -
13h
Negishi E.Qian MX.Zeng FX.Anastasia L.Babinski D. Org. Lett. 2003, 5: 1597 -
14a
Muehldorf AV.Guzman-Perez A.Kluge AF. Tetrahedron Lett. 1994, 35: 8755 -
14b
Tilley JW.Levitan P.Lind J.Welton AF.O’Donnell M. J. Med. Chem. 1987, 30: 185 -
14c
Clitherow JW.Scopes DC.Skingle M.Jorden CC. J. Med. Chem. 1994, 37: 2253 -
14d
Lammothe M.Pauwels PJ.Belliard K.Schambel P.Halazy S. J. Med. Chem. 1997, 40: 3542 -
15a
Elsevier CJ.Kleijn H.Ruitenberg K.Vermeer P. J. Chem. Soc., Chem. Commun. 1983, 1529 -
15b
Elsevier CJ.Kleijn H.Boersma J.Vermeer P. Organometallics 1986, 5: 716 - 16
Heidenreich RG.Köhler K.Krauter JK.Pietsch J. Synlett 2002, 1118 -
17a
Gala D.Jenkins SJ.Kugelman M. Org. Proc. Res. Dev. 1997, 1: 163 -
17b
Dyer UC.Shapland PD.Tiffin PD. Tetrahedron Lett. 2002, 42: 1765 -
17c
McClure MS.Roschangar F.Hodson SJ.Millar A.Osterhout MH. Synthesis 2001, 1681 -
17d
Sakurai H.Tsukuda T.Hirao T. J. Org. Chem. 2002, 67: 2721 -
17e
Tagata T.Nishida M. J. Org. Chem. 2003, 68: 9412 -
17f
LeBlond CR.Andrews AT.Sun YK.Sowa JR. Org. Lett. 2001, 3: 1555 -
17g
Organ MG.Mayer S. J. Comb. Chem. 2003, 5: 118 -
17h
Accadi A.Cerichelli G.Chiarini M.Correa M.Zorzan D. Eur. J. Org. Chem. 2003, 4080 -
18a
Reardon P.Metts S.Crittendon C.Dangherity P.Parson EJ. Organometallics 1995, 14: 3810 -
18b
Hagiwara H.Shimizu Y.Hoshi T.Suzuki T. Tetrahedron Lett. 2001, 42: 4349 -
18c
Xie XF.Lu JP.Chen B.Han JJ.She XG.Pan XF. Tetrahedron Lett. 2004, 45: 809 -
18d
Mehnert CP.Weaver DW.Ying JY. J. Am. Chem. Soc. 1998, 120: 12289 -
18e
Khan SI.Grinstaff MW. J. Org. Chem. 1999, 64: 1077 -
19a
Potts KT.Horwitz CP.Fessak A.Keshavarz-K M.Nash KE.Toscano PJ. J. Am. Chem. Soc. 1993, 115: 10444 -
19b
Bleicher LS.Cosford NDP. Synlett 1995, 1115 -
19c
Cosford NDP.Bleicher L.Herbaut A.McCallum JS.Vernier JM. J. Med. Chem. 1996, 39: 3235 -
19d
Bleicher LS.Cosford NDP.Herbaut A.McCallum JS.McDonald IA. J. Org. Chem. 1998, 63: 1109 -
19e
Novak Z.Szabo A.Kotschy A. J. Org. Chem. 2003, 68: 3327 -
19f
Bates RW.Boonsombat J. J. Chem. Soc., Perkin Trans. 1 2001, 654 -
19g
Lopez-Deber MP.Castedo L.Granja JR. Org. Lett. 2001, 3: 2823 -
19h
Pal M.Subramanian V.Yeleswarapu KR. Tetrahedron Lett. 2003, 44: 8221 - 20
Koradin C.Dohle W.Rodriguez AL.Schmid B.Knochel P. Tetrahedron 2003, 59: 1571 - 21
Fairlamb IJS.Bäuerlein PS.Marrison LR.Dickinson JM. Chem. Commun. 2003, 632