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 2011(16): 2629-2638
DOI: 10.1055/s-0030-1260118
DOI: 10.1055/s-0030-1260118
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Furan Ring Opening - Pyridine Ring Closure: New Route to Quinolines under the Bischler-Napieralski Reaction Conditions
Further Information
Received
18 April 2011
Publication Date:
14 July 2011 (online)
Publication History
Publication Date:
14 July 2011 (online)
Abstract
A new approach to highly functionalized quinolines is proposed. This approach is based on the electrophilic recyclization of 2-[2-(acylamino)benzyl]furans under the Bischler-Napieralski reaction conditions.
Key words
furans - ring opening - ring closure - fused-ring systems - quinolines - Bischler-Napieralski reaction
-
1a
Bischler A.Napieralski B. Ber. Dtsch. Chem. Ges. 1893, 26: 1903 -
1b
Whaley WM.Govindachari TR. Org. React. 1951, 6: 74 -
1c
Fodor G.Nagubandi S. Tetrahedron 1980, 36: 1279 -
1d
Love BE. Org. Prep. Proced. Int. 1996, 28: 1 -
1e
Chrzanowska M.Rozwadowska MD. Chem. Rev. 2004, 104: 3341 - For recent examples, see:
-
2a
Zein AL.Dakhil OO.Dawe LN.Georghiou PE. Tetrahedron Lett. 2010, 51: 177 -
2b
LeGendre O.Pecic S.Chaudhary S.Zimmerman SM.Fantegrossi WE.Harding WW. Bioorg. Med. Chem. Lett. 2010, 20: 628 -
2c
Sobarzo-Sanchez E.Uriarte E.Santana L.Tapia RA.Lourido PP. Helv. Chim. Acta 2010, 93: 1385 -
2d
Kölzer M.Weitzel K.Göringer HU.Thines E.Opatz T. ChemMedChem 2010, 5: 1456 -
2e
Jadhav VB.Nayak SK.Guru Row TN.Kulkami MV. Eur. J. Med. Chem. 2010, 45: 3575 -
2f
Awuah E.Capretta A. J. Org. Chem. 2010, 75: 5627 -
2g
Caille F.Buron F.Toth E.Suzenet F. Eur. J. Org. Chem. 2011, 2120 - For recent examples, see:
-
3a
Lee C.-S.Liu C.-K.Chiang YL.Cheng Y.-Y. Tetrahedron Lett. 2008, 49: 481 -
3b
Czarnocki SJ.Wojtaciewicz K.Jozwiak AP.Maurin JK.Czarnocki Z.Drabowicz J. Tetrahedron 2008, 64: 3176 -
3c
da Silva WA.Rodrigues MT.Shankaraiah N.Ferreira RB.Andrade CKZ.Pilli RA.Santos LS. Org. Lett. 2009, 11: 3238 -
3d
Takahashi Y.Ishiyama H.Kubota T.Kobayashi J. Bioorg. Med. Chem. Lett. 2010, 20: 4100 -
3e
Brahmbhatt KG.Ahmed N.Sabde S.Mitra D.Singh IP.Bhutani KK. Bioorg. Med. Chem. Lett. 2010, 20: 4416 -
4a
Ohkubo M.Kuno A.Katsuta K.Ueda Y.Shirakawa K.Nakanishi H.Kinoshita T.Takasugi H. Chem. Pharm. Bull. 1996, 44: 778 -
4b
Liu J.Diwu Z.Leung W.-Y.Lu Y.Patch B.Haugland RP. Tetrahedron Lett. 2003, 44: 4355 - 5
Clarke K.Hughes CG.Humphries AJ.Scrowston RM. J. Chem. Soc. C 1970, 1013 - 6
Guillon J.Forfar I.Mamani-Matsuda M.Desplat V.Saliege M.Thiolat D.Massip S.Tabourier A.Leger J.-M.Dufaure B.Haumont G.Jarry C.Mossalayi D. Bioorg. Med. Chem. 2007, 15: 194 - 7
Zheng W.Nikulin VI.Konkar AA.Vansal SS.Shams G.Feller DR.Miller DD. J. Med. Chem. 1999, 42: 2287 -
8a
Besselievre R.Husson H.-P. Tetrahedron 1981, 37: 241 -
8b
Maftouh M.Besselievre R.Monsarrat B.Lesca P.Meunier B.Husson HP.Paoletti C. J. Med. Chem. 1985, 28: 708 -
8c
Bäckvall J.-E.Plobeck NA. J. Org. Chem. 1990, 55: 4528 -
9a
Clark MT.Chang J.Navran SS.Akbar H.Mukhopadhyay A.Amin H.Feller DR.Miller DD. J. Med. Chem. 1986, 29: 181 -
9b
Enzensperger C.Lehmann J. J. Med. Chem. 2006, 49: 6408 -
9c
Enzensperger C.Müller FKU.Schmalwasser B.Wiecha P.Traber H.Lehmann J. J. Med. Chem. 2007, 50: 4528 -
10a
Andres JI.Alcazar J.Alonso JM.Diaz A.Fernandez J.Gil P.Iturrino L.Matesanz E.Meert TF.Megens A.Sipido VK. Bioorg. Med. Chem. Lett. 2002, 12: 243 -
10b
Pawlowska J.Czarnocki Z.Wojtaciewicz K.Maurin JK. Tetrahedron: Asymmetry 2003, 14: 3335 -
11a
Wardrop AWH.Sainsbury GL.Harrison JM.Inch TD. J. Chem. Soc., Perkin Trans. 1 1976, 1279 -
11b
Heaney H.Shuhaibar KF. Tetrahedron Lett. 1994, 35: 2751 - 12
Umemiya H.Fukasawa H.Ebisawa M.Eyrolles L.Kawachi E.Eisenmann G.Gronemeyer H.Hashimoto Y.Shudo K.Kagechika H. J. Med. Chem. 1997, 40: 4222 -
13a
Cairns J.Clarkson TR.Hamersma JAM.Rae DR. Tetrahedron Lett. 2002, 43: 1583 -
13b
Cobo J.Nogueras M.Low JN.Rodriguez R. Tetrahedron Lett. 2008, 49: 7271 -
14a
Fu R.Xu X.Dang Q.Bai X. J. Org. Chem. 2005, 70: 10810 -
14b
Xu X.Guo S.Dang Q.Chen J.Bai X. J. Comb. Chem. 2007, 9: 773 - 15
Hunziker F.Fischer R.Kipfer P.Schmutz J.Bürki HR.Eichenberger E.White TG. Eur. J. Med. Chem. 1981, 16: 391 -
16a
Herz W.Tocker S. J. Am. Chem. Soc. 1955, 77: 3554 -
16b
Sano T.Toda J.Shoda M.Yamamoto R.Ando H.Isobe K.Hosoi S.Tsuda Y. Chem. Pharm. Bull. 1992, 40: 3145 - 17
Ogawa M.Koyanagi J.Sakuma K.Tanaka A.Yamamoto K. J. Heterocycl. Chem. 1999, 36: 819 - 18
Butin AV.Tsiunchik FA.Kostyukova ON.Trushkov IV. Khim. Geterotsikl. Soedin. 2010, 1900 - 19
Butin AV.Smirnov SK.Stroganova TA.Bender W.Krapivin GD. Tetrahedron 2007, 63: 474 - 20
Fitzpatrick JE.Milner DJ.White P. Synth. Commun. 1982, 12: 489 - 21
Butin AV.Smirnov SK.Tsiunchik FA.Uchuskin MG.Trushkov IV. Synthesis 2008, 2943 -
23a
Doi S.Shirai N.Sato Y. J. Chem. Soc., Perkin Trans. 1 1997, 2217 -
23b
Ishikawa T.Shimooka K.Narioka T.Noguchi S.Saito T.Ishikawa A.Yamazaki E.Harayama T.Seki H.Yamaguchi K. J. Org. Chem. 2000, 65: 9143 -
24a
Abaev VT.Gutnov AV.Butin AV.Zavodnik VE. Tetrahedron 2000, 56: 8933 -
24b
Hashmi ASK.Frost TM.Bats JW. J. Am. Chem. Soc. 2000, 122: 11553 -
24c
Yamamura K.Kawabata S.Kimura T.Eda K.Hashimoto M. J. Org. Chem. 2005, 70: 8902 -
24d
Tokumaru K.Arai S.Nishida A. Org. Lett. 2006, 8: 27 -
24e
Ueda I.Nishiura M.Takahashi T.Eda K.Hashimoto M.Yamamura K. Tetrahedron Lett. 2006, 47: 8535 -
24f
Abaev VT.Tsiunchik FA.Gutnov AV.Butin AV. J. Heterocycl. Chem. 2008, 45: 475 -
24g
Butin AV.Tsiunchik FA.Abaev VT.Zavodnik VE. Synlett 2008, 1145 -
24h
Chen Y.Lu Y.Li G.Liu Y. Org. Lett. 2009, 11: 3838 -
24i
Butin AV.Uchuskin MG.Pilipenko AS.Tsiunchik FA.Cheshkov DA.Trushkov IV. Eur. J. Org. Chem. 2010, 920 -
24j
El Kaïm L.Grimaud L.Wagschal S. Chem. Commun. 2011, 47: 1887 -
25a
Butin AV.Smirnov SK.Stroganova TA. J. Heterocycl. Chem. 2006, 43: 623 -
25b
Abaev VT.Dmitriev AS.Gutnov AV.Podelyakin SA.Butin AV. J. Heterocycl. Chem. 2006, 43: 1195 -
25c
Dmitriev AS.Abaev VT.Bender W.Butin AV. Tetrahedron 2007, 63: 9437 -
25d
Butin AV.Abaev VT.Mel’chin VV.Dmitriev AS.Pilipenko AS.Shashkov AS. Synthesis 2008, 1798 - 26 For a review dealing with methods
for the synthesis of quinolines, see:
Kouznetsov VV.Mendez LYV.Comez CMM. Curr. Org. Chem. 2005, 9: 141 - 27
Butin AV.Kostyukova ON.Tsiunchik FA.Uchuskin MG.Serdyuk OV.Trushkov IV. J. Heterocycl. Chem. 2011, 48: 684
References
CCDC 820334 (for 3a) contains the supplementary crystallographic data for this paper. Copies of the data can be obtained, free of charge, on application to the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK [Fax: +44(1223)336033; e-mail: deposit@ccdc.cam.ac.uk] or via www.ccdc.cam.ac.uk/data_request/cif.