Regioselective Palladium(0)-Catalyzed Cross-Coupling Reactions of 5,7-Dichloro-1,6-naphthyridine

Iftikhar Ali; Zahid Hassan; Martin Hein; Abiodun Falodun; Tamás Patonay; Alexander Villinger; Peter Langer

doi:10.1055/s-0032-1316540

Synthesis, Inhaltsverzeichnis

Synthesis 2012; 44(14): 2255-2263
DOI: 10.1055/s-0032-1316540

paper

Regioselective Palladium(0)-Catalyzed Cross-Coupling Reactions of 5,7-Dichloro-1,6-naphthyridine

Iftikhar Ali

^aInstitut für Chemie, Universität Rostock, Albert Einstein Str. 3a, 18059 Rostock, Germany

,

Zahid Hassan

^aInstitut für Chemie, Universität Rostock, Albert Einstein Str. 3a, 18059 Rostock, Germany

,

Martin Hein

^aInstitut für Chemie, Universität Rostock, Albert Einstein Str. 3a, 18059 Rostock, Germany

,

Abiodun Falodun

^aInstitut für Chemie, Universität Rostock, Albert Einstein Str. 3a, 18059 Rostock, Germany

^bDepartment of Pharmaceutical Chemistry, Faculty of Pharmacy, University of Benin, Benin City 30001, Nigeria

,

Tamás Patonay

^cDepartment of Organic Chemistry, University of Debrecen, Egyetem tér 1, 4032 Debrecen, Hungary

,

Alexander Villinger

^aInstitut für Chemie, Universität Rostock, Albert Einstein Str. 3a, 18059 Rostock, Germany

,

Peter Langer*

^aInstitut für Chemie, Universität Rostock, Albert Einstein Str. 3a, 18059 Rostock, Germany

^dLeibniz-Institut für Katalyse an der Universität Rostock e.V., Albert Einstein Str. 29a, 18059 Rostock, Germany

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Abstract

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Abstract

A variety of mono- and diarylated naphthyridine derivatives were prepared by site-selective Suzuki–Miyaura cross-coupling reactions of 5,7-dichloro-1,6-naphthyridine. The first attack occurs at position 5.

Key Words

catalysis - palladium - Suzuki reaction - naphthyridine - regioselectivity

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Referenzen

Refreences

1a Li JJ, Gribble GW. Palladium in Heterocyclic Chemistry . Pergamon Press; Oxford: 2000
1b Kalinin VN. Synthesis 1992; 413

2 Nicolaou KC, Bulger PG, Sarlah D. Angew. Chem. Int. Ed. 2005; 44: 4442
3 Schröter S, Stock C, Bach T. Tetrahedron 2005; 61: 2245

4a Chow WK, So CM, Lau CP, Kwong FY. J. Org. Chem. 2010; 75: 5109 ; and references therein
4b Wolfe JP, Singer RA, Yang BH, Buchwald SL. J. Am. Chem. Soc. 1999; 121: 9550
4c Miyaura N, Yanagi T, Suzuki A. Synth. Commun. 1981; 11: 513
4d Yang HQ, Li G, Ma ZC, Chao JB, Guo ZQ. J. Catal. 2010; 276: 123
4e Lee DH, Jin MJ. Org. Lett. 2011; 13: 252 ; and references therein
4f Hassan J, Sveignon M, Gozzi C, Shultz E, Lemaire M. Chem. Rev. 2002; 102: 1359
4g Anctil EJ. G, Snieckus V. J. Organomet. Chem. 2002; 653: 150
4h Stanforth SF. Tetrahedron 1998; 54: 263

5a The Naphthyridines . In The Chemistry of Heterocyclic Compounds . Vol. 63. Brown DJ. John Wiley & Sons; Hoboken: 2007
5b Moss GP. Pure Appl. Chem. 1998; 70: 143
5c Allen CF. H. Chem. Rev. 1950; 47: 275
5d Litvinov VP. Adv. Heterocycl. Chem 2006; 91: 189
5e Litvinov VP, Roman SV, Dyachenko VD. Russ. Chem. Rev. 2000; 69: 201

6a Abdelrazek FM, Kassab NA. L, Metwally NH, Sobhy NA. Eur. J. Chem. 2010; 1: 368 ; and references cited therein
6b Han ZG, Zhang G, Jiang B, Ma N, Shi F, Tu SJ. J. Comb. Chem. 2009; 11: 809 ; and references therein
6c Han ZG, Miao CB, Shi F, Ma N, Zhang G, Tu SJ. J. Comb. Chem. 2010; 12: 16 ; and references therein

7 Nishigaki S, Mizushima N, Yoneda F. J. Med. Chem. 1971; 14: 638
8 Tomita K, Tsuzuki Y, Shibamori KI, Tashima M, Kajikawa F, Sato Y, Kashimoto S, Chiba K, Hino K. J. Med. Chem. 2002; 45: 5564
9 Barreiro EJ, Camara CA, Verli H, Brazil-Más L, Castro NG, Cintra WM, Aracava Y, Rodrigues CR, Fraga CA. M. J. Med. Chem. 2003; 46: 1144

10a Marco JL, de los Rios C, Carreiras MC, Banos JE, Badia A, Vivas NM. Bioorg. Med. Chem. 2001; 9: 727
10b Marco JL, de los Rios C, Garcia AG, Villarroya M, Carreiras MC, Martins C, Eleuterio A, Morreale A, Orozco M, Luque FJ. Bioorg. Med. Chem. 2004; 12: 2199

11 Leonard JT, Gangadhar R, Gnanasam SK, Ramachandran S, Saravanan M, Sridhar SK. Biol. Pharm. Bull. 2002; 25: 798
12 Meredith EL, Ardayfio O, Beattie K, Dobler MR, Enyedy I, Gaul C, Hosagrahara V, Jewell C, Koch K, Lee W, Lehmann H, McKinsey TA, Miranda K, Pagratis N, Pancost M, Patnaik A, Phan D, Plato C, Qian M, Rajaraman V, Rao C, Rozhitskaya O, Ruppen T, Shi J, Siska SJ, Springer C, Eis MV, Vega RB, Matt AV, Yang L, Yoon T, Zhang JH, Zhu N, Monovich LG. J. Med. Chem. 2010; 53: 5400
13 de los Rios C, Egea J, Contelles JM, Leon R, Samadi A, Iriepa I, Moraleda I, Galvez E, Garcia AG, Lopez MG, Villarroya M, Romero A. J. Med. Chem. 2010; 53: 5129
14 Blum CA, Caldwell T, Zheng X, Bakthavatchalam R, Capitosti S, Brielmann H, Lombaert SD, Kershaw MT, Matson D, Krause JE, Cortright D, Crandall M, Martin WJ, Murphy BA, Boyce S, Jones AB, Mason G, Rycroft W, Perrett H, Conley R, Davies NB, Chenard BL, Hodgetts KJ. J. Med. Chem. 2010; 53: 3330
15 Hinschberger A, Butt S, Lelong VR, Boulouard M, Dumuis A, Dauphin F, Bureau R, Pfeiffer B, Renard P, Rault S. J. Med. Chem. 2003; 46: 138
16 Zhuang L, Wai JS, Embrey MW, Fisher TE, Egbertson MS, Payne LS, Guare JP. Jr, Vacca JP, Hazuda DJ, Felock PJ, Wolfe AL, Stillmock KA, Witmer MV, Moyer G, Schleif WA, Gabryelski LJ, Leonard YM, Lynch JJ. Jr, Michelson SR, Young SD. J. Med. Chem. 2003; 46: 453
17 Chan L, Jin H, Stefanac T, Lavallée JF, Falardeau G, Wang W, Bedard J, May S, Yuen L. J. Med. Chem. 1999; 42: 3023
18 Thompson AM, Connolly CJ. C, Hamby JM, Boushelle S, Hartl BG, Amar AM, Kraker AJ, Driscoll DL, Steinkampf RW, Patmore SJ, Vincent PW, Roberts BJ, Elliott WL, Klohs W, Leopold WR, Showalter HD. H, Denny WA. J. Med. Chem. 2000; 43: 4200 ; and references therein
19 CCDC-873323 and 873324 contain all crystallographic details of this publication and are available free of charge at www.ccdc.cam.ac.uk/conts/retrieving.html or can be ordered from the following address: Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB21EZ, UK; Fax: +44(1223)336033; or e-mail: deposit@ccdc.cam.ac.uk
20 Handy ST, Zhang Y. Chem. Commun. 2006; 299

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