Synthesis, Inhaltsverzeichnis PAPER © Georg Thieme Verlag Stuttgart ˙ New York Synthesis and Functionalization of 4-Halomethyl-1,3-selenazoles Karlheinz Geisler*, Wolf-Diethard Pfeiffer, Cornelia Müller, Elvira Nobst, Ehrenfried Bulka, Peter Langer*Institut für Chemie und Biochemie, Ernst-Moritz-Arndt-Universität Greifswald, Soldmannstr. 16, 17487 Greifswald, GermanyFax: +49(3834)964346; e-Mail: peter.langer@uni-greifswald.de; Artikel empfehlen Abstract Artikel einzeln kaufen Alle Artikel dieser Rubrik Abstract Double-functionalized, ionic and multivalent 1,3-selenazoles were prepared by nucleophilic displacement reactions of protected 4-halomethyl-2-amino-1,3-selenazoles. Key words cyclizations - heterocycles - nucleophilic additions - selenium - halogens Volltext Referenzen References 1 For the antibiotically active C-glycosyl selenazole selenazofurin, see: Goldstein BM. Kennedy SD. Hennen WJ. J. Am. Chem. Soc. 1990, 112: 8265 ; and references cited therein 2a Larsen R. 1,3-Selenazoles, In Comprehensive Heterocyclic Chemistry II Vol. 3: Shinkai I. Katritzky A. Rees CW. Scriven EFV. Elsevier Science; Oxford: 1996. Chapt. 8:. 2b Wirth T. Organoselenium Chemistry. Modern Developments in Organic Synthesis Springer; Berlin: 2000. 3a Koketsu M. Nada F. Ishihara H. Synthesis 2002, 195 3b Geisler K. Jacobs A. Künzler A. Mattes M. Girrleit I. Zimmermann B. Bulka E. Pfeiffer W.-D. Langer P. Synlett 2002, 1983 3c Lai L.-L. Reid DH. Synthesis 1993, 870 3d Ishihara H. Koketsu M. Fukuta Y. Nada F. J. Am. Chem. Soc. 2001, 123: 8408 3e Koketsu M. Fukuta Y. Ishihara H. Tetrahedron Lett. 2001, 42: 6333 3f Zhang P.-F. Chen Z.-C. Synthesis 2000, 9: 1219 3g Maeda H. Kambe N. Sonoda N. Fujiwara S.-I. Sini-ike T. Tetrahedron 1997, 53: 13667 3h Ogawa A. Miyaka J. Karasaki Y. Murai S. Sonoda N. J. Org. Chem. 1985, 50: 384 3i Kaminski R. Glass RS. Skowronska A. Synthesis 2001, 1308 3j Cohen VJ. Synthesis 1978, 668 4 Banert K. Toth C. Angew. Chem. Int. Ed. Engl. 1995, 34: 1627 ; Angew. Chem. 1995, 107, 1776, and references cited therein 5a Hartmann H. Eckert K. Schröder A. Angew. Chem. Int. Ed. 2000, 39: 556 ; Angew. Chem. 2000, 112, 567, and references cited therein 5b Keil D. Hartmann H. Zug I. Schröder A. J. Prakt. Chem. 2000, 342: 169 6 For 4-halomethyl-1,3-thiazoles, see: Simiti I., Farkas M., Silberg S.; Chem. Ber.; 1962, 95: 2672 7a For a preliminary communication, see: Geisler K. Meinke H.-J. Müller C. Nobst E. Bulka E. Wiss. Z. Univ. Greifswald 1988, 37: 1 7b for reactions of 4-chloromethyl-1,3-selenazoles, see: Kumar Y. Green R. Borysko KZ. Wise . Wotring LL. Townsend LB. J. Med. Chem. 1993, 36 : 3843 7c Hanson RN. Davis AM. J. Heterocycl. Chem. 1981, 18: 205 7d Shafiee A. Kiaeay G. Vosooghi M. J. Heterocycl. Chem. 1981, 18: 789 8 For the synthesis of 2, see: Bulka E. Ahlers K.-D. Tucek E. Chem. Ber. 1967, 10: 1367
