Copper(I) Iodide Catalyzed Synthesis
of Quinolinones via Cascade Reactions of 2-Halobenzocarbonyls with
2-Arylacetamides

Liangbing Fu; Xiaoli Huang; Deping Wang; Pinghua Zhao; Ke Ding

doi:10.1055/s-0030-1259983

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Synthesis 2011(10): 1547-1554
DOI: 10.1055/s-0030-1259983

PAPER

Copper(I) Iodide Catalyzed Synthesis of Quinolinones via Cascade Reactions of 2-Halobenzocarbonyls with 2-Arylacetamides

Liangbing Fu^a,b,1, Xiaoli Huang^a,b,1, Deping Wang^a,b, Pinghua Zhao^c, Ke Ding*^a
^a Laboratory of Regenerative Biology, Guangzhou Institute of Biomedicine and Health, Chinese Academy of Sciences, No. 190 Kai Yuan Road, Science Park, Guangzhou 510530, P. R. of China
Fax: +86(20)32015299; e-Mail: ding_ke@gibh.ac.cn;
^b Graduate School of Chinese Academy of Sciences, Chinese Academy of Sciences, No. 19 A Yuquan Road, Shijingshan District, Beijing 100049, P. R. of China
^c GAC ChangFeng Motor Co. Ltd, YongZhou Branch, No. 68 Liebao North Road, Lengshuitan, Yongzhou, Hunan 425100, P. R. of China

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Publikationsverlauf

Received 13 February 2011
Publikationsdatum:
01. April 2011 (online)

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Abstract

An efficient copper-catalyzed method for the synthesis of quinolinones, pyridinones, and heteroannulated pyridinones via cascade reactions of substituted 2-iodo-, 2-bromo-, and 2-chlorobenzocarbonyls with 2-arylacetamides is reported. The protocol works well for the reaction of most of the 2-iodo-, 2-bromo- and 2-chlorobenzocarbonyls with 2-arylacetamides.

Key words

copper iodide - diamines - cascade reactions - amidation - quinolinones

Supporting Information

References

2a Chung HS. Woo WS. J. Nat. Prod. 2001, 64: 1579

Suche in Google Scholar
2b Ito C. Itoigawa M. Furukawa A. Hirano T. Murata T. Kaneda N. Hisada Y. Okuda K. Furukawa H. J. Nat. Prod. 2004, 67: 1800

Suche in Google Scholar
2c He J. Lion U. Sattler I. Gollmick FA. Grabley S. Cai J. Meiners M. Schünke H. Schaumann K. Dechert U. Krohn M. J. Nat. Prod. 2005, 68: 1397

Suche in Google Scholar
3a Oshiro Y. Sakurai Y. Sato S. Kurahashi N. Tanaka T. Kikuchi T. Tottori K. Uwahodo Y. Miwa T. Nishi T. J. Med. Chem. 2000, 43: 177

Suche in Google Scholar
3b Xiao Z. Waters NC. Woodard CL. Li Z. Li P.-K. Bioorg. Med. Chem. Lett. 2001, 11: 2875

Suche in Google Scholar
3c Chilin A. Marzano C. Guiotto A. Baccichetti F. Carlassare F. Bordin F. J. Med. Chem. 2002, 45: 1146

Suche in Google Scholar
3d Buchstaller H.-P. Siebert CD. Steinmetz R. Frank I. Berger ML. Gottschlich R. Leibrock J. Krug M. Steinhilber D. Noe CR. J. Med. Chem. 2006, 49: 864

Suche in Google Scholar
3e Freeman GA. Andrews CW. Hopkins AL. Lowell GS. Schaller LT. Cowan JR. Gonzales SS. Koszalka GW. Hazen RJ. Boone LR. Ferris RG. Creech KL. Roberts GB. Short SA. Weaver K. Reynolds DJ. Milton J. Ren J. Stuart DI. Stammers DK. Chan JH. J. Med. Chem. 2004, 47: 5923

Suche in Google Scholar
4a Sliskovic DR. Picard JA. Roark WH. Roth BD. Ferguson E. Krause BR. Newton RS. Sekerke C. Shaw MK. J. Med. Chem. 1991, 34: 367

Suche in Google Scholar
4b Suzuki M. Iwasaki H. Fujikawa Y. Kitahara M. Sakashita M. Sakoda R. Bioorg. Med. Chem. 2001, 9: 2727

Suche in Google Scholar
4c Bach T. Bergmann H. Grosch B. Harms K. J. Am. Chem. Soc. 2002, 124: 7982

Suche in Google Scholar
4d Kumabea R. Nishino H. Tetrahedron Lett. 2004, 45: 703

Suche in Google Scholar
5a Terpko MO. Heck RF. J. Am. Chem. Soc. 1979, 101: 5281

Suche in Google Scholar
5b Jia C.-S. Dong Y.-W. Tu S.-W. Wang G.-W. Tetrahedron 2007, 63: 892

Suche in Google Scholar
5c Tang D.-J. Tang B.-X. Li J.-H. J. Org. Chem. 2009, 74: 6749

Suche in Google Scholar
5d Kadnikov DV. Larock RC. J. Organomet. Chem. 2003, 687: 425

Suche in Google Scholar
5e Kim KH. Lee HS. Kim JN. Tetrahedron Lett. 2009, 50: 1249

Suche in Google Scholar
5f Marcaccini S. Pepino R. Pozo MC. Basurto S. Valverde MG. Torroba T. Tetrahedron Lett. 2004, 45: 3999

Suche in Google Scholar
5g Staskun B. J. Org. Chem. 1964, 29: 1153

Suche in Google Scholar
5h Marull M. Lefebvre O. Schlosser M. Eur. J. Org. Chem. 2004, 54
6a Manley PJ. Bilodeau MT. Org. Lett. 2004, 6: 2433

Suche in Google Scholar
6b Kadnikov DV. Larock RC. J. Org. Chem. 2004, 69: 6772

Suche in Google Scholar
6c Cortese NA. Ziegler CB. Hrnjez BJ. Heck RF. J. Org. Chem. 1978, 43: 2953

Suche in Google Scholar
7a Wang D. Cai Q. Ding K. Adv. Synth. Catal. 2009, 351: 1722

Suche in Google Scholar
7b Cai Q. Wei J. Fu L. Pei D. Ding K. Org. Lett. 2010, 12: 1500

Suche in Google Scholar
7c Chen H. Wang D. Wang X. Huang W. Cai Q. Ding K. Synthesis 2010, 1505
7d Cai Q. Li Z. Wei J. Ha C. Pei D. Ding K. Chem. Commun. 2009, 7581
7e Li Z. Fu L. Wei J. Ha C. Pei D. Cai Q. Ding K. Synthesis 2010, 3289
7f Zhou J. Fu L. Lv M. Liu J. Pei D. Ding K. Synthesis 2008, 3974
8a Wall M. J, Player M. R, Patch R. J, Meegalla S, Liu J, Illig C. R, Cheung W, Chen J, and Asgari D. inventors; PCT Int. Appl. WO 2005009967.
8b Wajon JFM. Arens JF. Recl. Trav. Chim. Pays-Bas 1957, 76: 65

Suche in Google Scholar
8c Blackburn TP. Cox B. Guildford AJ. Le Count DJ. Middlemiss DN. Pearce RJ. Thornber CW. J. Med. Chem. 1987, 30: 2252

Suche in Google Scholar
8d Bergman J. Brynolf A. Vuorinen E. Tetrahedron 1986, 42: 3689

Suche in Google Scholar

1

These two authors contributed equally to this work.