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 2007(8): 1214-1224
DOI: 10.1055/s-2007-966003
DOI: 10.1055/s-2007-966003
PAPER
© Georg Thieme Verlag Stuttgart · New York
Chlorotrimethylsilane-Mediated Friedländer Synthesis of Polysubstituted Quinolines
Further Information
Received
12 December 2006
Publication Date:
28 March 2007 (online)
Publication History
Publication Date:
28 March 2007 (online)
Abstract
New convenient conditions for the Friedländer synthesis of quinolines are described. Polysubstituted quinolines were readily prepared using chlorotrimethylsilane as a promoter and water-acceptor agent.
Key words
quinolines - annulation - o-amino aromatic carbonyls - chlorotrimethylsilane - parallel synthesis
- 1
Michael JP. Nat. Prod. Rep. 2001, 18: 543 -
2a
Larsen RD.Corley EG.King AO.Carrol JD.Davis P.Verhoeven TR.Reider PJ.Labelle M.Gautheir JY.Xiang YB.Zambony RJ. J. Org. Chem. 1996, 61: 3398 -
2b
Chen YJ.Fang KC.Sheu J.-Y.Hsu SL.Tzeng CC. J. Med. Chem. 2001, 44: 2374 -
2c
Roma G.Braccio MD.Grossi G.Mattioli F.Chia M. Eur. J. Med. Chem. 2000, 35: 1021 -
3a
Kalluraya B.Sreenivasa S. Farmaco 1998, 53: 399 -
3b
Doube D.Blouin M.Brideau C.Chan C.Desmarais S.Eitheir D.Falgueyret JP.Friesen RW.Girard M.Girard Y.Guay J.Tagari P.Young RN. Bioorg. Med. Chem. Lett. 1998, 8: 1255 - 4
Maguire MP.Sheets KR.McVerty K.Spada AP.Zilberstein A. J. Med. Chem. 1994, 37: 2129 - 5
Musser JH.Chakraborty UR.Sciortino S.Gordon RJ.Khandwala A.Neiss ES.Pruss TP.Van Inwegen R.Weinrib I.Coutts SM. J. Med. Chem. 1987, 30: 96 - 6
Van Inwegen RJ.Khandwala A.Gordon R.Sonnio P.Coutts S.Joly S. J. Pharm. Exp. Ther. 1987, 24: 117 - 7
Gauthier JY.Jones T.Champion E.Charette L.Dehaven R.Ford-Hatchinson AW.Hoogsteen K.Lord A.Masson P.Piechuta H.Pong SS.Springer JP.Therein M.Zamboni R.Young RN. J. Med. Chem. 1990, 33: 2841 - 8
Jenekhe SA.Lu L.Alam MM. Macromolecules 2001, 34: 7315 ; and references therein -
9a
Gilchrust TL. Heterocyclic Chemistry 3rd ed.: Adison-Wesley Longman; Essex: 1997. p.158-164 -
9b
Jones G. In Comprehensive Heterocyclic Chemistry Vol. 2:Katritzky AR.Rees AR. Pergamon; Oxford: 1984. p.395 - A subset of recent work in this area includes:
-
10a
Lindeman RJ.Kirollos SK. Tetrahedron Lett. 1990, 31: 2689 -
10b
Strekowski L.Lin SY.Lee H.Zhang ZQ.Mason JC. Tetrahedron 1998, 54: 7947 -
10c
Crouse B.Begue JP.Daniele BD. J. Org. Chem. 2000, 65: 5009 -
10d
Cho SC.Kim BT.Kim T.-J.Shim SC. Chem. Commun. 2001, 2576 ; and references therein -
10e
Amii H.Kishkava Y.Uneyama K. Org. Lett. 2001, 3: 1109 -
10f
Jiang B.Yui-Gui S. J. Org. Chem. 2002, 67: 9449 -
10g
Yadav JS.Reddy BVS.Srinivasa Rao R.Navenkumar V.Nagaiah K. Synthesis 2003, 1610 -
10h
Du W.Curran DP. Org. Lett. 2003, 5: 1765 -
10i
Ishkawa T.Manabe S.Aikawa T.Kudo T.Saito S. Org. Lett. 2004, 6: 2361 -
10j
Sangu K.Fuchibe K.Akiyama T. Org. Lett. 2004, 6: 353 -
10k
Kobayashi K.Yoneda K.Miyamoto K.Morikawa O.Konishi H. Tetrahedron 2004, 60: 11639 - For recent reviews see:
-
10l
Kouznetsov VV.Vargaz Mendez LY.Melendez Gomez CM. Curr. Org. Chem. 2005, 9: 141 -
11a
Friedländer P. Ber. Dtsch. Chem. Ges. 1882, 15: 2572 -
11b
Cheng CC.Yan S.-J. Org. React. 1982, 28: 37 ; and references therein -
11c
Glaiali S.Chelussi G.Mudadu MS.Gastuat MA.Thumel RP. J. Org. Chem. 2001, 66: 4000 -
12a
Strekowski L.Czamy A. J. Fluor. Chem. 2000, 104: 281 -
12b
Hu Y.-Z.Zang G.Thummel RP. Org. Lett. 2003, 5: 2251 - 13
Wu J.Xia HG.Gao K. Org. Biomol. Chem. 2006, 4: 126 -
14a
Arcadi A.Chiarini M.Di Guespe S.Marinelly F. Synlett 2003, 203 -
14b
Yadav JS.Reddy BVS.Premalatha K. Synlett 2004, 963 -
14c
Varala R.Enugala R.Adapa SR. Synthesis 2006, 3825 -
15a
Song SJ.Cho SJ.Park DK.Kwon TW.Jenekhe SA. Tetrahedron Lett. 2003, 44: 255 -
15b
Jia CS.Zhang Z.Tu SJ.Wang GW. Org. Biomol. Chem. 2006, 4: 104 -
16a
Wang J.Fan X.Zhang X.Han Can L. Can. J. Chem. 2004, 82: 1192 -
16b
Palimkar SS.Siddiqui SA.Daniel T.Lahoti RJ.Srinivasan JV. J. Org. Chem. 2003, 68: 9371 -
16c
Karthikeyan G.Perumal PT. J. Heterocycl. Chem. 2004, 41: 1039 - For recent examples see:
-
17a
McNaughton BR.Miller BL. Org. Lett. 2003, 5: 4257 -
17b
Motokura K.Mizugaki K.Ebitani K.Kiyotomi K. Tetrahedron Lett. 2004, 45: 6029 - For the use of TMSCl as a condensation agent, see:
-
18a
Ryabukhin SV.Plaskon AS.Tverdokhlebov AV.Tolmachev AA. Synth. Commun. 2004, 34: 1483 -
18b
Ryabukhin SV.Plaskon AS.Volochnyuk DM.Tolmachev AA. Synlett 2004, 2287 -
18c
Heaney H.Papageorgeogu G.Wilkins RF. Tetrahedron 1997, 53: 2941 - For the use of TMSI as a condensation agent, see:
-
18d
Sabitha G.Reddy GSKK.Reddy KB.Yadav JS. Synthesis 2004, 263 -
18e
Sabitha G.Reddy GSKK.Reddy CS.Yadav JS. Synlett 2003, 858 -
18f
Sabitha G.Reddy GSKK.Reddy CS.Yadav JS. Tetrahedron Lett. 2003, 44: 4129 -
18g
Ryabukhin SV.Plaskon AS.Volochnyuk DM.Tolmachev AA. Synthesis 2006, 3715 -
18h
Ryabukhin SV.Plaskon AS.Ostapchuk EN.Volochnyuk DM.Tolmachev AA. Synthesis 2007, 417 - For recent examples of derivatives of quinolin-3-ylacetic acid used in lead optimization, see:
-
19a
Wattanasin S.Albert R.Ehrhardt C.Roche D.Sabio N.Hommel U.Welzenbach K.Weitz-Schmidt G. Bioorg. Med. Chem. Lett. 2003, 13: 499 -
19b
Li B.de Laszlo SE.Kamenecka TM.Kopka IE.Durette PL.Lanza T.MacCoss M.Tong S.Mumford RA.McCauley ED.Van Riper E.Schmidt JA.Hagmann WK. Bioorg. Med. Chem. Lett. 2002, 12: 2141 - For the synthesis of derivatives of 3-(carboxymethyl)quin-oline-4-carboxylic acid via the Pfitzinger approach see:
-
20a
Buu-Hoi NP.Cagniant P. Chem. Ber. 1943, 76: 126 - For the synthesis of derivatives of (2-chloroquinolin-3-yl)acetic acid see:
-
20b
Meth-Cohn O.Rhouati S.Tarnowski B.Robinson A. J. Chem. Soc., Perkin Trans. 1 1981, 1537 -
21a
Bamberg P.Johansson B. Acta Chem. Scand. 1968, 22: 2422 -
21b
Sakamoto T.Kondo Y.Masumoto K.Yamanaka H. Heterocycles 1993, 36: 2509 -
21c
Sakamoto T.Katoh E.Kondo Y.Yamanaka H. Chem. Pharm. Bull. 1988, 36: 1664 -
21d
Joergensen M.Lee S.Liu X.Wolkowski JP.Hartwig JF. J. Am. Chem. Soc. 2002, 124: 12557 -
22a
Kempter G.Möbius G. J. Prakt. Chem. 1966, 34: 298 -
22b
Meyer Ev.Berge P.Oehler R.Schletter E. J. Prakt. Chem. 1914, 90: 1 -
22c
Kauffmann T.Woltermann A. Angew. Chem., Int. Ed. Engl. 1972, 11: 842 ; Angew. Chem. 1972, 84, 824 -
22d
Kempter G.Hirschberg S. Chem. Ber. 1965, 98: 419 -
22e
Fehnel EA. J. Org. Chem. 1966, 31: 2899 -
22f
Kempter G.Andertschky P.Heilmann D.Krausmann H.Mictorch M. Chem. Ber. 1964, 97: 16 -
22g
Kempter G.Zanker P.Zurner H. Arch. Pharm. Ber. Dtsch. Pharm. Ges. 1967, 300: 829 - 23
Anzini M.Vomero S.Garofalo A.Cappelli A.Cagnotto A. Farmaco 1989, 44: 555 - 24
Vasse J.-L.Levacher V.Bourguignon J.Dupas G. Tetrahedron: Asymmetry 2002, 13: 227 -
25a
Ried W.Berg A.Schmidt G. Chem. Ber. 1952, 85: 204 -
25b
Moon MP.Komin AP.Wolfe JF.Morris GF. J. Org. Chem. 1983, 48: 2392 - 26
Anzini M.Capelli A.Vomero S. Heterocycles 1994, 38: 103 -
27a
Molina P.Conesa C.Alias A.Arques A.Velasco MD.Llamas-Saiz AL.Foces-Foces C. Tetrahedron 1993, 49: 7599 -
27b
Kempter G.Moebius G. J. Prakt. Chem. 1966, 34: 298 - 28 For similar mechanism of Friedlander condensation, see:
Muchowski JM.Maddox ML. Can. J. Chem. 2004, 82: 461
References
www.enamine.net.