Abstract
When subjected to tandem SN 2′-SN Ar
cyclization in the presence of alkyl or aralkyl amines, Baylis-Hillman
acetates gave the corresponding 1,2-dihydroquinolines, which on
simple exposure to light and oxygen afforded the corresponding 4-
and 2-quinolones through sensitized oxidation or a Δ³,4 -Δ²,³ shift → oxidation cascade.
The mechanism of the oxidation step, the stabilities of the 1,2-
and 1,4-dihydroquinolines in solution and in the solid state, and the
synthetic elaboration of the key intermediates to known therapeutic
agents are discussed.
Key words
antibiotics - cyclizations - quinolines - radical
reactions - photooxidations
References
<A NAME="RT52311SS-1">1 </A>
Emmerson AM.
Jones AM.
J. Antimicrob. Chemother.
2003,
51:
13
<A NAME="RT52311SS-2">2 </A>
Anderson VR.
Perry CM.
Drugs
2008,
68:
535
<A NAME="RT52311SS-3">3 </A>
Wolfson JS.
Hooper DC.
Ann. Intern. Med.
1988,
108:
238
<A NAME="RT52311SS-4">4 </A>
Raja A.
Lebbos J.
Kirkpatrick P.
Nat.
Rev. Drug Discovery
2004,
3:
733
<A NAME="RT52311SS-5">5 </A>
Sato M.
Kawakami H.
Motomura T.
Aramaki H.
Matsuda T.
Yamashita M.
Ito Y.
Matsuzaki Y.
Yamataka K.
Ikeda S.
Shinkai H.
J. Med.
Chem.
2009,
52:
4869
<A NAME="RT52311SS-6">6 </A>
Hadjeri M.
Peiller E.-L.
Beney C.
Deka N.
Lawson MA.
Dumontet C.
Boumendjel A.
J.
Med. Chem.
2004,
47:
4964
<A NAME="RT52311SS-7">7 </A>
Mahmoudi N.
Ciceron L.
Franetich J.-F.
Farhati K.
Silvie O.
Eling W.
Sauerwein R.
Danis M.
Mazier D.
Derouin F.
Antimicrob. Agents Chemother.
2003,
47:
2636
<A NAME="RT52311SS-8">8 </A>
Ito C.
Itoigawa M.
Furukawa A.
Hirano T.
Murata T.
Kaneda N.
Hisada Y.
Okuda K.
Furukawa H.
J. Nat. Prod.
2004,
67:
1800
<A NAME="RT52311SS-9">9 </A>
Joseph B.
Darro F.
Béhard A.
Lesur B.
Collignon F.
Decaestecker C.
Frydman A.
Guillaumet G.
Kiss R.
J.
Med. Chem.
2002,
45:
2543
<A NAME="RT52311SS-10">10 </A>
Hopkins AL.
Ren J.
Milton J.
Hazen RJ.
Chan JH.
Stuart DI.
Stammers DK.
J. Med. Chem.
2004,
47:
5912
<A NAME="RT52311SS-11">11 </A>
Boteva AA.
Krasnykh OP.
Chem. Heterocycl.
Compd. (Engl. Transl.)
2009,
45:
757 ;
and references cited therein
<A NAME="RT52311SS-12">12 </A>
Huang J.
Chen Y.
King AO.
Dilmeghani M.
Larsen RD.
Faul MM.
Org. Lett.
2008,
10:
2609
<A NAME="RT52311SS-13">13 </A>
Mitscher LA.
Chem.
Rev.
2005,
105:
559 ;
and references cited therein
<A NAME="RT52311SS-14">14 </A>
Gould RG.
Jacobs WA.
J.
Am. Chem. Soc.
1939,
61:
2890
<A NAME="RT52311SS-15">15 </A>
Bouzard D.
Di Cesare P.
Essiz M.
Jacquet JP.
Remuzon P.
Weber A.
Oki T.
Masuyoshi M.
J. Med. Chem.
1989,
32:
537 ; and references cited therein
<A NAME="RT52311SS-16">16 </A>
Hong WP.
Lee K.-J.
Synthesis
2006,
963
<A NAME="RT52311SS-17">17 </A>
Kim JN.
Lee KY.
Kim HS.
Kim TY.
Org. Lett.
2000,
2:
343
<A NAME="RT52311SS-18">18 </A>
Kim JN.
Lee KY.
Ham H.-S.
Kim HR.
Ryu EK.
Bull.
Korean Chem. Soc.
2001,
22:
135
<A NAME="RT52311SS-19">19 </A>
Amarante GW.
Benassi M.
Pascoal RN.
Eberlin MN.
Coelho F.
Tetrahedron
2010,
66:
4370
<A NAME="RT52311SS-20">20 </A>
Lee KY.
Kim JM.
Kim JN.
Bull.
Korean Chem. Soc.
2002,
23:
1493
<A NAME="RT52311SS-21">21 </A>
Lee KY.
Kim JN.
Bull. Korean Chem. Soc.
2002,
23:
939
<A NAME="RT52311SS-22">22 </A>
Basavaiah D.
Reddy RM.
Kumaragurubaran N.
Sharada DS.
Tetrahedron
2002,
58:
3693
<A NAME="RT52311SS-23">23 </A>
Felpin F.-X.
Coste J.
Zakri C.
Fouquet E.
Chem. Eur. J.
2009,
15:
7238
<A NAME="RT52311SS-24">24 </A>
Pathak R.
Madapa S.
Batra S.
Tetrahedron
2006,
63:
451
<A NAME="RT52311SS-25">25 </A>
Kim KH.
Lee HS.
Kim JN.
Tetrahedron
Lett.
2009,
50:
1249
<A NAME="RT52311SS-26">26 </A>
Taylor SM.
Stubley-Beedham C.
Stell JGP.
Biochem. J.
1984,
220:
67
<A NAME="RT52311SS-27">27 </A>
Oleinick NL.
Morris RL.
Belichenko I.
Photochem. Photobiol.
Sci.
2002,
1:
1
<A NAME="RT52311SS-28">28 </A>
Sissi C.
Palumbo M.
Curr. Med. Chem.: Anti-Cancer Agents
2003,
3:
439
<A NAME="RT52311SS-29">29 </A>
Bunting JW.
Fitzgerald NP.
Can. J. Chem.
1985,
63:
655
<A NAME="RT52311SS-30">30 </A>
Crystallographic data for compounds 4a (R4 = Bn), 6.7 , and 7.7 have
been deposited with the Cambridge Crystallographic Data Centre as
supplementary publications CCDC 779998, CCDC 771058, and CCDC 771059, respectively;
copies can be obtained free of charge on application to CCDC, 12
Union Road, Cambridge CB2 1EZ, UK [fax: +44 (1223)336033
or email: deposit@ccdc.cam.ac.uk].
<A NAME="RT52311SS-31">31 </A>
Kim JN.
Kim HS.
Gong JH.
Chung YM.
Tetrahedron Lett.
2001,
42:
8341
<A NAME="RT52311SS-32">32 </A>
Ferroud C.
Rool P.
Santamaria J.
Tetrahedron
Lett.
1998,
39:
9423
<A NAME="RT52311SS-33">33 </A>
Darmanyan AP.
Lee W.
Jenks WS.
J.
Phys. Chem. A
1999,
103:
2705
<A NAME="RT52311SS-34">34 </A>
Roberts RMG.
Ostovic D.
Kreevoy MM.
J. Org. Chem.
1983,
48:
2053
<A NAME="RT52311SS-35">35 </A>
Alberti MN.
Orfanopoulos M.
Chem. Eur. J.
2010,
16:
9414
<A NAME="RT52311SS-36">36 </A>
Stratakis M.
Orfanopoulos M.
Tetrahedron
2000,
56:
1595
<A NAME="RT52311SS-37">37 </A>
Fukuzumi S.
Ishikawa M.
Tanaka T.
J.
Chem. Soc., Perkin Trans. 2
1989,
1037
<A NAME="RT52311SS-38">38 </A>
Raghuvanshi RS.
Singh KN.
Indian J. Chem., Sect.
B: Org. Chem. Incl. Med. Chem.
2008,
47:
1735
<A NAME="RT52311SS-39">39 </A>
Memarian HR.
Abdoli-Senejani M.
Tangestaninejad S.
J.
Iran. Chem. Soc.
2006,
3:
285
<A NAME="RT52311SS-40">40 </A>
Zerbes R,
Naab P,
Franckowiak G, and
Diehl H. inventors; US Patent 5639886.
<A NAME="RT52311SS-41">41 </A>
Mokrushina GA.
Kotovskaya SK.
Baskakova ZM.
Petrova GM.
Kolmakova TV.
Charushin VN.
Rusinov VL.
Chupakhin ON.
Khim.-Farm. Zh.
1996,
30:
46
<A NAME="RT52311SS-42">42 </A>
Volle J.-N.
Schlosser M.
Eur. J. Org. Chem.
2000,
823
<A NAME="RT52311SS-43">43 </A>
Han E.-G.
Kim HJ.
Lee K.-J.
Tetrahedron
2009,
65:
9616
<A NAME="RT52311SS-44">44 </A>
O’Del DK.
Nicholas KM.
J.
Org. Chem.
2003,
68:
6427
<A NAME="RT52311SS-45">45 </A>
Yoshikawa K.
Kobayashi S.
Nakamoto Y.
Haginoya N.
Komoriya S.
Yoshino T.
Nagata T.
Mochizuki A.
Watanabe K.
Suzuki M.
Kanno H.
Ohta T.
Bioorg. Med. Chem.
2009,
17:
8221
