Summary.
Aromatic aldehydes undergo condensation with quinaldines under microwave irradiation to afford structurally diverse styrylquinolines in high yields under solvent-free conditions. A comparison with the conventional method clearly indicates the advantages of the new protocol.
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K Mekouar JF Mouscadet D Desmaele F Subra H Leh D Savoure C Auclair J d’Angelo (1998) J Med Chem 41 2846 Occurrence Handle1:CAS:528:DyaK1cXksVKqtLc%3D Occurrence Handle10.1021/jm980043e
F Zouhiri M Danet C Bernard M Normand-Bayle J-F Mouscadet H Leh CM Thomas G Mbemba J d’Angelo D Desmaele (2005) Tetrahedron Lett 46 2201 Occurrence Handle1:CAS:528:DC%2BD2MXhvF2gu7s%3D Occurrence Handle10.1016/j.tetlet.2005.02.033
M Ouali C Laboulais H Leh D Gill D Desmaele Kh Mekouar F Zouhiri C Auclair J d’Angelo JF Mouscadet M Le Bret (2000) J Med Chem 43 1949 Occurrence Handle1:CAS:528:DC%2BD3cXivVaisr4%3D Occurrence Handle10.1021/jm9911581
J Polanski F Zouhiri L Jeanson D Desmaële J d’Angelo JF Mouscadet R Gieleciak J Gasteiger M Le Bret (2002) J Med Chem 45 4647 Occurrence Handle1:CAS:528:DC%2BD38XmvFWlur8%3D Occurrence Handle10.1021/jm020845g
Ch Bernard F Zouhiri M Normand-Bayle M Danet D Desmaele H Leh JF Mouscadet G Mbemba C Thomas M Bonnenfant M Le Bret J d’Angelo (2004) Bioorg Med Chem Lett 14 2473 Occurrence Handle10.1016/j.bmcl.2004.03.005 Occurrence Handle1:CAS:528:DC%2BD2cXjsVKhtrs%3D
Y Pommier AA Johnson C Marchand (2005) Nat Rev Drug Discov 4 236 Occurrence Handle1:CAS:528:DC%2BD2MXhslSns70%3D Occurrence Handle10.1038/nrd1660
E Ochiai (1967) Aromatic Amine Oxides Elsevier New York
AR Katritzky JM Lagowski (1971) Chemistry of the heterocyclic N-oxides Academic Press New York
EC Taylor SF Martin (1974) J Am Chem Soc 96 8095 Occurrence Handle1:CAS:528:DyaE2MXhs1Oqsg%3D%3D Occurrence Handle10.1021/ja00833a601
Giam CS, Stout JL (1969) J Chem Soc D 142
E Ochiai I Kuniyoshi (1957) Pharm Bull 5 292 Occurrence Handle1:CAS:528:DyaG1cXot1GktA%3D%3D
T Higashino E Hayashi (1970) Chem Pharm Bull 18 1457 Occurrence Handle1:CAS:528:DyaE3cXks1KmsLc%3D
Cooper GG, Rickard RL (1971) J Chem Soc C 772
EC Taylor SF Martin (1972) J Am Chem Soc 94 2874 Occurrence Handle1:CAS:528:DyaE38XktVGnsb4%3D Occurrence Handle10.1021/ja00763a064
JP Phillips R Breese EM Barrall (1959) J Org Chem 24 104 Occurrence Handle10.1021/jo01090a017
P Lidstrom J Tierney B Wathey J Westman (2001) Tetrahedron 57 9225 Occurrence Handle1:CAS:528:DC%2BD3MXnvFWlsrY%3D Occurrence Handle10.1016/S0040-4020(01)00906-1
S Caddic (1995) Tetrahedron 51 10403 Occurrence Handle10.1016/0040-4020(95)00662-R
For more comprehensive reviews see also: a) Loupy A (Ed) (2002) Microwaves in Organic synthesis, Wiley-VCH, Weinheim; b) Hayes BL (2002) Microwave synthesis: chemistry at the speed of light, CEM Publishing, Matthews, NC; c) Varma RS (2002) Advances in Green Chemistry: Chemical Syntheses Using Microwave Irradiation, Astra Zeneca Research Foundation, Kavitha Printers, Bangalore, India; d) Kappe CO, Stadtler A (2005) Microwaves in Organic and Medicinal Chemistry, Wiley-VCH, Weinheim
Musiol R, Niedbala H, Majerz-Maniecka K, Mrowczyk A, Oleksyn B, Polanski J (2005) Annals Pol Chem Soc (in print)
Majerz-Maniecka K, Oleksyn B, Musiol R, Podeszwa B, Polanski J (2005) Joint Meeting on Med Chem Vienna, Austria, June 20–23: PO-136
JF Dippy RM Evans (1950) J Org Chem 15 451 Occurrence Handle1:CAS:528:DyaG3cXkvFamuw%3D%3D Occurrence Handle10.1021/jo01149a001
a) Miller V (1890) Chem Ber 23: 2272; b) Glen WL, Bailey CC (1941) J Am Chem Soc 63: 639; c) Mills JT, Harris J, Lambounre LJ (1927) J Chem Soc 119: 1298
J Polanski H Niedbala R Musiol D Tabak B Podeszwa R Gieleciak A Bak A Palka T Magdziarz (2004) Acta Poloniae Pharm 61 3 Occurrence Handle1:CAS:528:DC%2BD2MXkslGgsrY%3D
Polanski J, Niedbala H, Musiol R, Podeszwa B, Tabak D, Palka A, Mencel A, Mouscadet JF, Gieleciak R, Bak A, Magdziarz, LeBret M (2005) J Med Chem (submitted)
K Majerz-Maniecka R Musiol W Nitek BJ Oleksyn JF Mouscadet M LeBret J Polanski (2006) Bioorg Med Chem Lett 16 5 Occurrence Handle10.1016/j.bmcl.2005.10.083 Occurrence Handle1:CAS:528:DC%2BD28Xhs1Crtg%3D%3D
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Musiol, R., Podeszwa, B., Finster, J. et al. An Efficient Microwave-Assisted Synthesis of Structurally Diverse Styrylquinolines. Monatsh. Chem. 137, 1211–1217 (2006). https://doi.org/10.1007/s00706-006-0513-1
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DOI: https://doi.org/10.1007/s00706-006-0513-1