Synthesis, Table of Contents PAPER © Georg Thieme Verlag Stuttgart · New York Convenient Synthesis of Substituted 3-Alkenylpyrazolo[1,5-a]pyrimidines via Heck Cross-Coupling Reaction Lunxiang Yin, Jürgen Liebscher*Institut für Chemie, Humboldt-Universität Berlin, Brook-Taylor-Straße 2, 12489 Berlin, GermanyFax: +49(30)20937552; e-Mail: liebscher@chemie.hu-berlin.de; Recommend Article Abstract Buy Article All articles of this category Abstract 3-Iodopyrazolo[1,5-a]pyrimidines 3 were easily obtained by direct iodination of pyrazolo[1,5-a]pyrimidines 2 with NIS and could be transformed into a series of new substituted 3-alkenyl-pyrazolo[1,5-a]pyrimidines 5 by Heck cross-coupling. Key Words heterocycles - pyrazolo[1,5-a]pyrimidines - iodination - Heck reaction Full Text References References 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 Karanik M. Pätzel M. Liebscher J. Synthesis 2003, 1201 10a Li JJ. Gribble GW. Palladium in Heterocyclic Chemistry Pergamon; Oxford: 2000. 10b Kalinin VN. Synthesis 1991, 413 10c Sakamoto T. Kondo Y. Yamanaka H. Heterocycles 1988, 27: 2225 11 Shioto T. Yamamori T. J. Org. Chem. 1999, 64: 453 12 Vattoly JM. Jaya PJ. John MJS. Dileep K. Adv. Synth. Catal. 2003, 345: 620 13a Heck RF. Norry JP. J. Org. Chem. 1972, 37: 2320 13b Whitcombe NJ. Hii KK. Gibson SE. Tetrahedron 2001, 57: 7449 13c Kundu NG. Nandi B. J. Org. Chem. 2001, 66: 4563 14 Bellec C. Lhommet G. J. Heterocycl. Chem. 1995, 32: 1793 15a Petrov AA. Emelina EE. Firsov AV. Russ. J. Org. Chem. 2000, 36: 1027 15b Danagulyan GG. Pannosyan GA. Boyakhchyan AP. Chem. Heterocycl. Comp. 2002, 38: 581 15c Emelina EE. Petrov AA. Firsov AV. Russ. J. Org. Chem. 2001, 37: 899 16 Allen WE. Fowler CJ. Lynch VM. Sessler JL. Chem.-Eur. J. 2001, 7: 721 17a Nugent RA. Dunn CJ. Staite ND. Murphy MJ. Schlachter ST. Aspar DG. Shields SK. Galinet L. Phosphorus, Sulfur, Silicon Relat. Elem. 1996, 109-110: 229 17b Krasovsky AL. Hartulyari AS. Nenajdenko VG. Balenkova ES. Synthesis 2002, 133 18a Kirkpatrick WE. Okabe T. Hillyard IW. Robins RK. Dren AT. Novinson T. J. Med. Chem. 1977, 20: 389 18b Elmoghayar MRH. Ibrahim MKA. El-Sakka I. Elghandour HH. Elnagdi MH. Arch. Pharm. (Weinheim, Ger) 1983, 316: 697 19 Liebscher J. Neumann B. Hartmann H. J. Prakt. Chem. 1983, 325: 915 20 Hartmann H. Liebscher J. Synthesis 1984, 276