Synthesis, Inhaltsverzeichnis Synthesis 2015; 47(20): 3139-3146DOI: 10.1055/s-0034-1381010 paper © Georg Thieme Verlag Stuttgart · New YorkPalladium-Catalyzed Synthesis of 1H-Pyrazolo[4,3-c]quinolines and 4-Anilinoquinoline-3-carbonitriles from 4-Chloroquinoline-3-carbaldehydes Chao Wang Department of Chemistry, Fudan University, 200433 Shanghai, P. R. of China eMail: qrwang@fudan.edu.cn , Caifei Tang Department of Chemistry, Fudan University, 200433 Shanghai, P. R. of China eMail: qrwang@fudan.edu.cn , Zhiming Li Department of Chemistry, Fudan University, 200433 Shanghai, P. R. of China eMail: qrwang@fudan.edu.cn , Quanrui Wang* Department of Chemistry, Fudan University, 200433 Shanghai, P. R. of China eMail: qrwang@fudan.edu.cn› InstitutsangabenArtikel empfehlen Abstract Artikel einzeln kaufen Alle Artikel dieser Rubrik Abstract Novel 1H-pyrazolo[4,3-c]quinolines and 4-anilinoquinoline-3-carbonitriles were prepared from readily accessible 4-chloroquinoline-3-carbaldehyde hydrazones by palladium-catalyzed intramolecular C–N bond formation and concurrent hydrazine N–N bond fission. These two classes of functionalized quinolines were chromatographically separable, and both are of biological interest. The ratio of the two products was found to be temperature-dependent; by changing the reaction temperature, either the pyrazoloquinoline or the anilinoquinolinecarbonitrile can become the dominant product. Key words Key wordshydrazones - palladium - cross-coupling - fused-ring systems - nitriles - pyrazoloquinolines Volltext Referenzen References and Notes 1a Savini L, Chiasserini L, Pellerano C, Biggio G, Maciocco E, Serra V, Cinone N, Carrieri A, Altomare C, Carotti A. Bioorg. Med. Chem. 2001; 9: 431 1b Carotti A, Altomare C, Savini L, Chiasserini L, Pellerano C, Mascia MP, Maciocco E, Busonero F, Mameli M, Biggio G, Sanna E. Bioorg. Med. Chem. 2003; 11: 5259 2 Skotnicki J, Gilman CS, Steinbaugh AB, Musser HJ. US 4748246, 1988 ; Chem. Abstr. 1988, 109, 110425 3 Baruah B, Dasu K, Vaitilingam B, Vanguri A, Casturi SR, Yeleswarapu KR. Bioorg. Med. Chem. Lett. 2004; 14: 445 4 Crespo IM, Gràcia J, Puig C, Vega A, Bou J, Beleta J, Doménech T, Ryder H, Segarra V, Palacios JM. Bioorg. Med. Chem. Lett. 2000; 10: 2661 5 Wentland MP. US 5334595, 1994 ; Chem. Abstr. 1994, 121, 230766. 6 Suzuki F, Nakasato Y, Ohmori K, Tamura T, Hosoe H, Kubo K, Yoshitake I. EP 0476544, 1992 ; Chem. Abstr. 1992, 116, 255609. 7 Kasiotis KM, Fokialakis N, Haroutounian SA. Synthesis 2006; 1791 8 Gaurav A, Gautam V, Singh R. Mini-Rev. Med. Chem. 2010; 10: 1194 9 Cin GT, Demirel S, Cakici A. J. Organomet. Chem. 2011; 696: 613 10 For a review on recent developments in the chemistry of pyrazolo[4,3-c]quinolines, see: Mekheimer RA, Ahmed EA, Sadek KU. Tetrahedron 2012; 68: 1637 11a Maluleka MM, Mphahlele MJ. Tetrahedron 2013; 69: 699 11b Ashok K, Stidevi G, Devi YU, Heckendron R, Winkler T. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1993; 32: 786 12 Wissner A, Overbeek E, Reich MF, Floyd MB, Johnson BD, Mamuya N, Rosfjord EC, Discafani C, Davis R, Shi X, Rabindran SK, Gruber BC, Ye F, Hallett WA, Nilakantan R, Shen R, Wang Y.-F, Greenberger LM, Tsou H.-R. J. Med. Chem. 2003; 46: 49 13a Cortes JE, Kantarjian HM, Brümmendorf TH, Kim DW, Turkina AG, Shen ZX, Pasquini R, Khoury HJ, Arkin S, Volkert A, Besson N, Abbas R, Wang J, Leip E, Gambacorti-Passerini C. Blood 2013; 118: 4567 ; Erratum: Blood 2013, 122, 2524 13b Cortes JE, Kim DW, Kantarjian HM, Brümmendorf TH, Dyagil I, Griskevicus L, Malhotra H, Powell C, Gogat K, Countouriotis AM, Gambacorti-Passerini C. J. Clin. Oncol. 2012; 30: 3486 14 Zhang S, Zhu L, Liu W, Zhang L, Rao Z, Wen J, Gong P. Zhongguo Yaowu Huaxue Zazhi 2010; 20: 269 ; Chem. Abstr. 2010, 154, 409800 15a Li C, Li Z, Wang Q. Synlett 2010; 2179 15b Tang C, Li Z, Wang Q. Beilstein J. Org. Chem. 2013; 9: 2629 15c Tang C, Wang C, Li Z, Wang Q. Synthesis 2014; 46: 2734 16 Marson CM. Tetrahedron 1992; 48: 3659 17a Meth-Cohn O. Heterocycles 1993; 35: 539 ; and references cited therein 17b Amaresh RR, Perumal PT. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1997; 36: 541 17c Seixas RS. G. R, Silva AM. S, Alkorta I, Elguero J. Monatsh. Chem. 2011; 142: 731 17d Seixas RS. G. R, Silva AM. S, Cavaleiro JA. S. Synlett 2010; 2257 17e Abdel-Wahab BF, Khidre RE, Farahat AA, El-Ahl A.-AS. ARKIVOC 2012; (i): 211 18 Gaywood AP, McNab H. Org. Biomol. Chem. 2010; 8: 5166 19 Paul S, Gupta M, Gupta R, Loupy A. Tetrahedron Lett. 2001; 42: 3827 20 Mali JR, Pratap UR, Jawale DV, Mane RA. Tetrahedron Lett. 2010; 51: 3980 21 For use in the synthesis of indol-3-yl benzonaphthyridines by copper(II) triflate catalyzed heteroannulation, see: Prakash KS, Nagarajan R. Tetrahedron Lett. 2013; 54: 3635 22 Harikrishna B, Soumya B, Sanjay B. Org. Lett. 2012; 14: 6330 23 For a micro-review, see: Kienle M, Dubbaka SR, Brade K, Knochel P. Eur. J. Org. Chem. 2007; 4166 24a Muci AR, Buchwald SL. Top. Curr. Chem. 2002; 219: 131 24b Jiang L, Buchwald SL In Metal-Catalyzed Cross-Coupling Reactions . 2nd ed., Vol. 1; de Meijere A, Diederich F. Wiley-VCH; Weinheim: 2004: 699 25a Driver MS, Hartwig JF. J. Am. Chem. Soc. 1996; 118: 7217 25b Marcoux J.-F, Wagaw S, Buchwald SL. J. Org. Chem. 1997; 62: 1568 For palladium-catalyzed coupling of aldehyde-derived hydrazones, see: 26a Thiel OR, Achmatowicz MM, Reichelt A, Larsen RD. Angew. Chem. Int. Ed. 2010; 49: 8395 ; Angew. Chem. 2010, 122, 8573 26b Shen Q, Shekhar S, Stambuli JP, Hartwig JF. Angew. Chem. Int. Ed. 2005; 44: 1371 ; Angew. Chem. 2005, 117, 1395 26c Shirbin SJ, Boughton BA, Zammit SC, Zanatta SD, Marcuccio SM, Hutton CA, Williams SJ. Tetrahedron Lett. 2010; 51: 2971 27 Kokel B, Menichi G, Hubert-Habart MA. Synthesis 1985; 201 28a Młlochowski J, Kloc K, Kubicz E. J. Prakt. Chem. 1994; 336: 467 28b Kamal A, Arifuddin M, Rao NV. Synth. Commun. 1998; 28: 4507 29 Crystallographic data for compounds 4a and 5a have been deposited with the accession numbers CCDC 1036104 and 1036103, respectively, and can be obtained free of charge from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; Fax: +44(1223)336033; E-mail: deposit@ccdc.cam.ac.uk; Web site: www.ccdc.cam.ac.uk/conts/retrieving.html. Zusatzmaterial Zusatzmaterial Supporting Information
