Synthesis, Inhaltsverzeichnis PAPER © Georg Thieme Verlag Stuttgart · New York A Facile Access to 2-CF3-Imidazo[1,2-a]pyridines Arcady L. Krasovsky, Valentine G. Nenajdenko*, Elizabeth S. BalenkovaDepartment of Chemistry, Moscow State University, 119899 Moscow, RussiaFax: +7(095)9328846; e-Mail: Nen@acylium.chem.msu.ru; Artikel empfehlen Abstract Artikel einzeln kaufen Alle Artikel dieser Rubrik Abstract A new simple and efficient way to 2-CF3-imidazo[1,2-a]pyridines and 2-CF3-imidazo[1,2-a]quinolines by the reaction of 1,1,1-trifluoro-4-(phenylsulfonyl)but-3-ene-2,2-diols 1a,b with various 2-aminopyridines is described. The cyclization reaction proceeds diastereospecifically under mild conditions in water. Key words diastereoselectivity - cycloaddition - heterocycles - imidazo[1,2-a]pyridines - imidazo[1,2-a]quinolines - sulfones Volltext Referenzen References 1 Trapani G. Franco M. Ricciardi L. Latrofa A. Genchi G. Sanna E. Tuveri F. Cagetti E. Biggio G. Liso G. J. Med. Chem. 1997, 40: 3109 2 Hamdouchi C. de Blas J. del Prado M. Gruber J. Heinz BA. Vance L. J. Med. Chem. 1999, 42: 50 3 Gueiffier A. Mavel S. Lhassani M. Elhakmaoui A. Snoeck R. Andrei G. Chavignon O. Teulade J.-C. Witvrouw M. Balzarini J. De Clercq E. Chapat J.-P. J. Med. Chem. 1998, 41: 5108 ; and references cited therein 4 Kelly JL. McLean EW. Davis RG. Grouch R. J. Heterocycl. Chem. 1990, 27: 1821 5a Bonnet PA. Michel A. Laurent F. Sablayrolles C. Rechencq E. Mani JC. Boucard M. Chapat J.-P. J. Med. Chem. 1992, 35: 3353 ; and references cited therein 5b Yamanaka M. Miyake K. Syda S. Ohhara H. Ogawa T. Chem. Pharm. Bull. 1991, 39: 1556 5c Bochis RJ. Olen LE. Fisher MH. Reamer RA. Wilks G. Taylor JE. Olson G. J. Med. Chem. 1981, 24: 1483 5d Bochis RJ. Dybas RA. Eskola P. Kulsa P. Linn BO. Lusi A. Meitzner EP. Milkowski J. Morzik H. Olen LE. Peterson AH. Tolman RL. Wagner AF. Waksmunski FS. Egerton JR. Ostlind DA. J. Med. Chem. 1978, 21: 235 6a Kaminski JJ. Doweyko AM. J. Med. Chem. 1997, 40: 427 6b Abe Y. Kayakiri H. Satoh S. Inoue T. Sawada Y. Imai K. Inamura N. Asano M. Hatory C. Katayama A. Oku T. Tanaka H. J. Med. Chem. 1998, 41: 564 7a Tschitschibabin AE. Ber. Dtsch. Chem. Ges. 1924, 57: 2092 7b Kauner CB. Pandit VK. Heterocycles 1978, 9: 757 7c Abignente E. Capraous P. Fallorusso E. Mayol L. J. Heterocycl. Chem. 1989, 26: 1875 8a Moutou J.-L. Schmitt M. Collot V. Bourguignon J.-J. Heterocycles 1997, 45: 897 ; and references cited therein 8b Blackburn C. Guan B. Fleming P. Shiosaki K. Tsai S. Tetrahedron Lett. 1998, 39: 3635 9a Varma RS. Kumar D. Tetrahedron Lett. 1999, 40: 7665 9b Bienayme H. Bouzid K. Angew. Chem. Int. Ed. 1998, 37: 2234 9c Blackburn C. Guan B. Fleming P. Shiosaki K. Tsai S. Tetrahedron Lett. 1998, 39: 3635 9d Blackburn C. Tetrahedron Lett. 1998, 39: 5469 9e Blackburn C. Guan B. Tetrahedron Lett. 1999, 40: 1495 10 Kröhnke F. Kickhöfen B. Thoma C. Chem. Ber. 1955, 88: 1117 11 Hand ES. Paudler WW. J. Org. Chem. 1978, 43: 658 12 Vega JA. Vaquero JJ. Alvarez-Builla J. Ezquerra J. Hamdouchi C. Tetrahedron 1999, 55: 2317 13a Tominaga Y. Shiroshita Y. Hosomi A. Heterocycles 1988, 27: 2251 13b Tominaga Y. Hosomi A. J. Heterocycl. Chem. 1988, 25: 1449 14 Alcock NW. Golding BT. Hall DR. Horn U. Watson WP. J. Chem. Soc., Perkin Trans. 1 1975, 386 15 Artyomov VA. Shestopalov AM. Litvinov VP. Synthesis 1996, 927 16a Knoelker H.-J. Boese R. Hitzemann R. Chem. Ber. 1990, 123: 327 16b Knoelker H.-J. Boese R. J. Chem. Soc., Chem. Commun. 1988, 1151 16c Knoelker H.-J. Hitzemann R. Tetrahedron Lett. 1994, 35: 2157 16d Knoelker H.-J. Boese R. Hitzemann R. Heterocycles 1989, 29: 1551 17a Potts KT. Kanamasa S. J. Org. Chem. 1979, 44: 3803 17b Magtti CV. Villani FJ. J. Heterocycl. Chem. 1978, 15: 1021 18 Chayer S. Schmitt M. Collot V. Bourguignon J.-J. Tetrahedron Lett. 1998, 39: 9685 19a Hamdouchi C. Sanchez C. Ezquerra J. Synthesis 1998, 867 19b Hamdouchi C. de Blas J. Ezquerra J. Tetrahedron 1999, 55: 541 20 Barum O. Ila H. Junjappa H. Mukherjee OS. J. Org. Chem. 2000, 65: 1583 21 Katritzky AR. Qui G. Long Q.-H. He H.-Y. Steel PJ. J. Org. Chem. 2000, 65: 9201 22a Nenajdenko VG. Krasovsky AL. Lebedev ML. Balenkova ES. Synlett 1997, 1349 22b Krasovsky AL. Nenajdenko VG. Balenkova ES. Tetrahedron 2001, 57: 201 23 Krasovsky AL. Nenajdenko VG. Balenkova ES. Russ. Chem. Bull. 2001, 50: 1395 24 Gerus II. Gorbunova MG. Vdovenko SI. Yagupolski JuL. Kukhar VP. J. Org. Chem. USSR (Engl. Transl.) 1990, 26: 1623 25 Sanin AV. Nenajdenko VG. Balenkova ES. Russ. Chem. Rev. 1999, 68: 483