Synthesis of Symmetrical and Unsymmetrical N-Aryl-Substituted Cyclic Ureas through Copper(I) Iodide Catalyzed Goldberg-Buchwald-Nandakumar C-N Coupling Reactions

Chung-Chieh Lee; Po-Shih Wang; M. Balaji Viswanath; Man-kit Leung

doi:10.1055/s-2008-1042946

PAPER

Synthesis of Symmetrical and Unsymmetrical N-Aryl-Substituted Cyclic Ureas through Copper(I) Iodide Catalyzed Goldberg-Buchwald-Nandakumar C-N Coupling Reactions

Chung-Chieh Lee^a, Po-Shih Wang^a, M. Balaji Viswanath^a, Man-kit Leung*^a,b
^a Department of Chemistry, National Taiwan University, 1 Roosevelt Road, Section 4, Taipei, Taiwan 106
^b Institute of Polymer Science and Engineering, National Taiwan University, 1 Roosevelt Road, Section 4, Taipei, Taiwan 106
Fax: +886(2)33636359; e-Mail: mkleung@ntu.edu.tw;

Abstract

Alle Artikel dieser Rubrik

Abstract

The catalytic conditions of copper(I) iodide/potassium carbonate/trans-N,N′-dimethylcyclohexane-1,2-diamine, either in toluene at reflux temperature, or by heating neat at 150 °C effectively promoted the C-N coupling of aryl bromides with cyclic ureas. By employing a protection-deprotection strategy, unsymmetrical diaryl-substituted cyclic ureas could also be synthesized.

Key words

arylation - copper - cross-coupling - homogeneous catalysis - heterocycles

Volltext

Referenzen

References

1a Guichou J.-F. Viaud J. Mettling C. Subra G. Lin Y.-L. Chavanieu A. J. Med. Chem. 2006, 49: 900

1b Muccioli GG. Wouters J. Charlier C. Scriba GKE. Pizza T. Di Pace P. De Martino P. Poppitz W. Poupaert JH. Lambert DM. J. Med. Chem. 2006, 49: 872

1c Du X. Hansell E. Engel JC. Caffrey CR. Cohen FE. Mckerrow JH. Chem. Biol. 2000, 7: 733

2a Garozzo D. Gattuso G. Notti A. Pappalardo A. Pappalardo S. Parisi MF. Perez M. Pisagatti I. Angew. Chem. Int. Ed. 2005, 44: 4892

2b Xu S. Podoprygorina G. Böhmer V. Ding Z. Rooney P. Rangan C. Mittler S. Org. Biomol. Chem. 2007, 5: 558

2c Rudzevich Y. Rudzevich V. Schollmeyer D. Thondorf I. Böhmer V. Org. Biomol. Chem. 2006, 4: 3938

3a Wu Y. Peng X. Fan J. Gao S. Tian M. Zhao J. Sun S. J. Org. Chem. 2007, 72: 62

3b Kim Y.-J. Kwak H. Lee SJ. Lee JS. Kwon HJ. Nam SH. Lee K. Kim C. Tetrahedron 2006, 62: 9635

3c Brooks SJ. Gale PA. Light ME. Chem. Commun. 2006, 4344

For reviews:

4a Denisko OV. In Comprehensive Organic Functional Group Transformations II Vol. 6: Katritzky AR. Taylor RJK. Elsevier; Amsterdam: 2005. p.453

4b Vishnyakova TP. Golubeva IA. Glebova EV. Russ. Chem. Rev. (Engl. Transl.) 1985, 54: 249

5a Barnes DM. Haight AR. Hameury T. McLaughlin MA. Mei J. Tedrow JS. Dalla Riva Toma J. Tetrahedron 2006, 62: 11311

5b Hwang SH. Morisseau C. Do Z. Hammock BD. Bioorg. Med. Chem. Lett. 2006, 16: 5773

5c Anderson MO. Yu H. Penaranda C. Maddux BA. Goldfine ID. Youngren JF. Guy RK. J. Comb. Chem. 2006, 8: 784

6a Barnes MJ. Conroy R. Miller DJ. Mills JS. Montana JG. Pooni PK. Showell GA. Walsh LM. Warneck JBH. Bioorg. Med. Chem. Lett. 2007, 17: 354

6b Lu W.-B. Zhou X.-H. Ren J.-G. Inorg. Chem. Commun. 2005, 8: 789

6c Kassack MU. Braun K. Ganso M. Ullmann H. Nickel P. Böing B. Müller G. Lambrecht G. Eur. J. Med. Chem. 2004, 39: 345

7a Orito K. Miyazawa M. Nakamura T. Horibata A. Ushito H. Nagasaki H. Yuguchi M. Yamashita S. Yamazaki T. Tokuda M. J. Org. Chem. 2006, 71: 5951

7b Shi F. Zhang Q. Gu Y. Deng Y. Adv. Synth. Catal. 2005, 347: 225

7c Gabriele B. Salerno G. Mancuso R. Costa M. J. Org. Chem. 2004, 69: 4741

7d Hiwatari K. Kayaki Y. Okita K. Ukai T. Shimizu I. Yamamoto A. Bull. Chem. Soc. Jpn. 2004, 77: 2237

For reviews:

8a Jiang L. Buchwald SL. In Metal-Catalyzed Cross-Coupling Reactions Vol. 2: de Meijere A. Diederich F. Wiley-VCH; Weinheim: 2004. p.699

8b Hartwig JF. In Handbook of Organopalladium Chemistry for Organic Synthesis Vol. 1: Negishi E. Wiley-Interscience; New York: 2002. p.1051

8c Hartwig JF. Angew. Chem. Int. Ed. 1998, 37: 2046

8d Wolfe JP. Wagaw S. Marcoux J.-F. Buchwald SL. Acc. Chem. Res. 1998, 31: 805

For recent examples see:

8e Morris DJ. Docherty G. Woodward G. Wills M. Tetrahedron Lett. 2007, 48: 949

8f Willis MC. Brace GN. Findlay TJK. Holmes IP. Adv. Synth. Catal. 2006, 348: 851

8g Klingensmith LM. Strieter ER. Barder TE. Buchwald SL. Organometallics 2006, 25: 82

8h Abbiati G. Beccalli EM. Broggini G. Paladino G. Rossi E. Synthesis 2005, 2881

8i Yin J. Buchwald SL. J. Am. Chem. Soc. 2002, 124: 6043

8j Rivas FM. Giessert AJ. Diver ST. J. Org. Chem. 2002, 67: 1708

9a Sergeev AG. Artamkina GA. Beletskaya IP. Tetrahedron Lett. 2003, 44: 4719

9b Artamkina GA. Sergeev AG. Beletskaya IP. Tetrahedron Lett. 2001, 42: 4381

9c Sergeev AG. Artamkina GA. Beletskaya IP. Russ. J. Org. Chem. 2003, 39: 1741

9d Artamkina GA. Sergeev AG. Beletskaya IP. Russ. J. Org. Chem. 2002, 38: 538

9e Lee S.-g. Zhang YJ. Song CE. Lee JK. Choi JH. Angew. Chem. Int. Ed. 2002, 41: 847

9f Glettner B. Hein S. Reddy A. Baumeister U. Tschierske C. Chem. Commun. 2007, 2596

10 Abad A. Agulló C. Cuñat AC. Vilanova C. Synthesis 2005, 915

11 Ferraccioli R. Carenzi D. Synthesis 2003, 1383

12 Klapars A. Huang X. Buchwald SL. J. Am. Chem. Soc. 2002, 124: 7421

13a Goldberg I. Ber. Dtsch. Chem. Ges. 1906, 39: 1691

13b Freeman HS. Bulter JR. Freedman LD. J. Org. Chem. 1978, 43: 4975

13c Renger B. Synthesis 1985, 856

13d Carrasco R. Pellón RF. Elguero J. Goya P. Páez JA. Synth. Commun. 1989, 19: 2077

13e Ito A. Saito T. Tanaka K. Yamabe T. Tetrahedron Lett. 1995, 36: 8809

13f Lange JHM. Hofmeyer LJF. Hout FAS. Osnabrug SJM. Verveer PC. Kruse CG. Feenstra RW. Tetrahedron Lett. 2002, 43: 1101

For reviews:

14a Lindley J. Tetrahedron 1984, 40: 1433

14b Ley SV. Thomas AW. Angew. Chem. Int. Ed. 2003, 42: 5400

14c Beletskaya IP. Cheprakov AV. Coord. Chem. Rev. 2004, 248: 2337

14d Kunz K. Scholz U. Ganzer D. Synlett 2003, 2428

15 Klapars A. Antilla JC. Huang X. Buchwald SL. J. Am. Chem. Soc. 2001, 123: 7727

16 Strieter ER. Blackmond DG. Buchwald SL. J. Am. Chem. Soc. 2005, 127: 4120

For recent advanced modifications:

17a Lv X. Bao W. J. Org. Chem. 2007, 72: 3863

17b Chen Y.-J. Chen H.-H. Org. Lett. 2006, 8: 5609

17c Guo X. Rao H. Fu H. Jiang Y. Zhao Y. Adv. Synth. Catal. 2006, 348: 2197

17d Chandrasekhar S. Sultana SS. Yaragorla SR. Reddy NR. Synthesis 2006, 839

17e Moriwaki K. Satoh K. Takada M. Ishino Y. Ohno T. Tetrahedron Lett. 2005, 46: 7559

17f Deng W. Wang Y.-F. Zou Y. Liu L. Guo Q.-X. Tetrahedron Lett. 2004, 45: 2311

Examples of synthetic applications, see:

17g Klapars A. Parris S. Anderson KW. Buchwald SL. J. Am. Chem. Soc. 2004, 126: 3529

17h Cuny G. Bois-Choussy M. Zhu J. J. Am. Chem. Soc. 2004, 126: 14475

17i Barros OSdR. Nogueira CW. Stangherlin EC. Menezes PH. Zeni G. J. Org. Chem. 2006, 71: 1552

17j Wang S. Sun J. Yu G. Hu X. Liu JO. Hu Y. Org. Biomol. Chem. 2004, 2: 1573

17k Zou B. Yuan Q. Ma D. Org. Lett. 2007, 9: 4291

18a Buchwald SL, Klapars A, Antilla JC, Job GE, Wolter M, Kwong FY, Nordmann G, and Hennessy EJ. inventors; WO 02,085,838.

18b Nandakumar MV. Tetrahedron Lett. 2004, 45: 1989

18c Hafner T. Kunz D. Synthesis 2007, 1403

19a Leung Mk. Lai J.-L. Lau J.-H. Yu H.-h. Hsiao H.-J. J. Org. Chem. 1996, 61: 4175

19b Liao C.-F. Lai JL. Chen J.-A. Chen H.-T. Cheng H.-L. Her G .-R. Su JK. Wang Y. Lee GH. Leung M.-k. Wang C.-C. J. Org. Chem. 2001, 66: 2566

19c Chen J.-A. Lai J.-L. Lee GH. Wang Y. Su JK. Yeh H.-C. Lin W.-Y. Leung M.-k. Org. Lett. 2001, 3: 3999

19d Chien C.-H. Leung M.-k. Su J.-K. Li G.-H. Liu Y.-H. Wang Y. J. Org. Chem. 2004, 69: 1866

19e Wang P.-S. Liang C.-K. Leung Mk. Tetrahedron 2005, 61: 2931

20

While DMF is a teratogen, dioxane is a carcinogen suspect agent.

21 Gulbins E. Hamann K. Chem. Ber. 1966, 99: 62

22 Rowbottom MW. Vickers TD. Tamiya J. Zhang M. Dyck B. Grey J. Schwarz D. Heise CE. Hedrick M. Wen J. Tang H. Wang H. Fisher A. Aparicio A. Saunders J. Goodfellow VS. Bioorg. Med. Chem. Lett. 2007, 17: 2171

23 Kuenzel HE. Bentz F. Wolf GD. Blankenstein G. Nischk G. Makromol. Chem. 1970, 138: 223

24 McKay AF. Tarlton EJ. J. Am. Chem. Soc. 1952, 74: 2978

25 Bates HA. Condulis N. Stein NL. J. Org. Chem. 1986, 51: 2228

26 Meth-Cohn O. Yan Z. J. Chem. Soc., Perkin Trans. 1 1998, 423

27 Antilla JC. Klapars A. Buchwald SL. J. Am. Chem. Soc. 2002, 124: 11684