Abstract
New, potentially bioactive, imidazopyridine derivatives were synthesized in a highly efficient synthesis in four steps from 2-amino-3,5-dibromopyridine using microwave-assisted double Suzuki-Miyaura cross-coupling methodology.
Key words
double cross-coupling - microwaves - imidazo[1,2-a ]pyridine - sulfones - spectroscopy
References
1a Kazock J.-Y.
Enguehard-Gueiffier C.
Théry I.
Gueiffier A.
Bull. Chem. Soc. Jpn.
2005,
78:
154
1b Knoelker H.-J.
Boese R.
Hitzemann R.
Chem. Ber.
1990,
123:
327
2a Gueiffier A.
Lhassani M.
Elhakmaoui A.
Snoeck R.
Andrei G.
Chavignon O.
Teulade J.-C.
Kerbal A.
Essassi EM.
Debouzy J.-C.
Witvrouw M.
Blache Y.
Balzarini J.
De Clercq E.
Chapat J.-P.
J. Med. Chem.
1996,
39:
2856
2b 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
2c Lhassani M.
Chavignon O.
Chezal J.-M.
Teulade J.-C.
Chapat J.-P.
Snoeck R.
Andrei G.
Balzarini J.
De Clercq E.
Gueiffier A.
Eur. J. Med. Chem.
1999,
34:
271
3 Kaplan JP, and George P. inventors; EP 0050563.
; Chem. Abstr. 1982 , 97 , 149531a
4a Kaminski JJ.
Bristol JA.
Puchalski C.
Lovey RG.
Elliot AJ.
Guzik H.
Solomon DM.
Conn DJ.
Domalski MS.
Wong S.-C.
Gold EH.
Long JF.
Chiu PJS.
Steinberg M.
McPhail AT.
J. Med. Chem.
1985,
28:
876
4b Kaminski JJ.
Doweyko AM.
J. Med. Chem.
1997,
40:
427
5 Sanfilippo P.
Urbanski M.
Press JB.
Dubinsky B.
Moore JB.
J. Med. Chem.
1988,
31:
2221
6a George P, and Allen J. inventors; EP 267111.
; Chem. Abstr.
1988 , 109 , 149531a
6b Allen J, and George P. inventors; FR 2612928.
; Chem. Abstr.
1988 , 111 , 174090
6c George P, Allen J, and Jaurand G. inventors; FR 2612927.
; Chem. Abstr.
1988 , 111 , 115178
6d Allen J, and George P. inventors; FR 2606411.
; Chem. Abstr.
1988 , 110 , 57665
6e Allen G, and George P. inventors; FR 2599368.
; Chem. Abstr.
1987 , 109 , 170422
6f George P, and Giron C. inventors; EP 172096.
; Chem. Abstr.
1986 , 105 , 97458
6g Kaplan J.-P, and George P. inventors; EP 92458.
; Chem. Abstr.
1983 , 100 , 103345
6h Kaplan J.-P, George P, and Bernardon JM. inventors; EP 92459.
; Chem. Abstr.
1983 , 100 , 139102
7a The Chemistry of Sulphones and Sulphoxides
Patai S.
Rappoport Z.
Stirling C.
John Wiley and Sons;
Chichester:
1988.
7b Simpkins NS.
Sulphones in Organic Synthesis
Pergamon Press;
Oxford:
1993.
7c Blakemore PR.
J. Chem. Soc., Perkin Trans. 1
2002,
2563
8 Kudo N.
Perseghini M.
Fu GC.
Angew. Chem. Int. Ed.
2006,
45:
1282
9 Crozet MD.
Castera C.
Kaafarani M.
Crozet MP.
Vanelle P.
ARKIVOC
2003,
(x):
273
10a Enguehard C.
Renou J.-L.
Collot V.
Hervet M.
Rault S.
Gueiffier A.
J. Org. Chem.
2000,
65:
6572
10b Enguehard C.
Hervet M.
Théry I.
Renou J.-L.
Fauvelle F.
Gueiffier A.
Helv. Chim. Acta
2001,
84:
3610
10c Enguehard-Gueffier C.
Hübner H.
El Hakmaoui A.
Allouchi H.
Gmeiner P.
Argiolas A.
Melis MR.
Gueiffier A.
J. Med. Chem.
2006,
49:
3938
11 Kotha S.
Lahiri K.
Kashinath D.
Tetrahedron
2002,
58:
9633 ; and references therein
12a Bracher F.
Daab J.
Eur. J. Org. Chem.
2002,
2288
12b Baldwin JE.
Adlington RM.
Conte A.
Irlapati NR.
Marquez R.
Pritchard GJ.
Org. Lett.
2002,
4:
2125
12c Couve-Bonnaire S.
Carpentier J.-F.
Mortreux A.
Castanet Y.
Tetrahedron
2003,
59:
2793
12d Berthiol F.
Kondolff I.
Doucet H.
Santelli M.
J. Organomet. Chem.
2004,
689:
2786
12e Prediger P.
Moro AV.
Nogueira CW.
Savegnago L.
Menezes PH.
Rocha JBT.
Zeni G.
J. Org. Chem.
2006,
71:
3786
13 Castera C.
Crozet MD.
Crozet MP.
Vanelle P.
Heterocycles
2005,
65:
337
14a Badone D.
Baroni M.
Cardamone R.
Ielmini A.
Guzzi U.
J. Org. Chem.
1997,
62:
7170
14b Moreno-Mañas M.
Pajuelo F.
Pleixats R.
J. Org. Chem.
1995,
60:
2396
14c Wallow TI.
Novak BM.
J. Org. Chem.
1994,
59:
5034
14d O’Keefe DF.
Dannock MC.
Marcuccio SM.
Tetrahedron Lett.
1992,
33:
6679
14e Migita T.
Nagai T.
Kiuchi K.
Kosugi M.
Bull. Chem. Soc. Jpn.
1983,
56:
2869
14f Organic Synthesis in Water
Grieco PA.
Blackie Academic and Professional;
London:
1997.
14g Li C.-J.
Chan TH.
Organic Reactions in Aqueous Media
Kluwer Academic;
Dordrecht:
1997.
15a Arvela RK.
Leadbeater NE.
Mack TL.
Kormos CM.
Tetrahedron Lett.
2006,
47:
217
15b Arvela RK.
Leadbeater NE.
Org. Lett.
2005,
7:
2101
15c Arvela RK.
Leadbeater NE.
Sangi MS.
Williams VA.
Granados P.
Singer RD.
J. Org. Chem.
2005,
70:
161
15d Liu L.
Zhang Y.
Wang Y.
J. Org. Chem.
2005,
70:
6122
15e Botella L.
Najera C.
Angew. Chem. Int. Ed.
2002,
41:
179
15f Leadbeater NE.
Marco M.
Org. Lett.
2002,
4:
2973
16 Senn-Bilfinger J, Buhr W, and Zimmermann P. inventors; WO 200172748.
; Chem. Abstr. 2001 , 135 , 272961
17 Bussolari JC.
Rehborn DC.
Org Lett.
1999,
1:
965
18a Roberts BA.
Strauss CR.
Acc. Chem. Res.
2005,
38:
653
18b Larhed M.
Moberg C.
Hallberg A.
Acc. Chem. Res.
2002,
35:
717
18c Song YS.
Kim BT.
Heo J.-N.
Tetrahedron Lett.
2005,
46:
5987 ; and references cited therein
18d Microwaves in Organic Synthesis
Loupy A.
Wiley-VCH;
Weinheim:
2006. and references cited therein
19 Kashin AN.
Mitin AV.
Mitin AV.
Beletskaya IP.
Wife R.
Tetrahedron Lett.
2002,
43:
2539
20 Detailed X-ray crystallographic data are available from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2, 1EZ, UK (for compound 4 , CCDC 659668; 5 , CCDC 659669; 6 , CCDC 659670). These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
