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 2002(10): 1379-1384
DOI: 10.1055/s-2002-33106
DOI: 10.1055/s-2002-33106
PAPER
© Georg Thieme Verlag Stuttgart · New York
A Facile Access to 2-CF3-Imidazo[1,2-a]pyridines
Further Information
Received
10 April 2001
Publication Date:
01 August 2002 (online)
Publication History
Publication Date:
01 August 2002 (online)
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
- 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