Copper-Catalyzed Synthesis of N-Heterocyclic Compounds

Abstract

The synthesis of N-heterocyclic compounds is an important direction because of their diverse biological functions. Recently, there has been remarkable progress in copper-catalyzed cross couplings with inexpensive, readily available, insensitive-to-air and low-toxicity copper catalysts. This review summarizes recent advances in the copper-catalyzed synthesis of N-heterocyclic compounds.

1 Introduction and Background

2 Synthesis of Five-Membered Heterocycles with One Nitrogen Atom

2.1 Pyrrolidine and Pyrrole Derivatives

2.2 Indole Derivatives

2.3 Indolone and Isoindolone Derivatives

2.4 Oxazole, Isoxazole, Benzoxazole and Benzothiazole Derivatives

3 Synthesis of Five-Membered Heterocycles with Two Nitrogen Atoms

3.1 Imidazole Derivatives

3.2 Benzimidazole Derivatives

3.3 Benzimidazolone Derivatives

4 Synthesis of N-Sulfonyltriazoles

5 Synthesis of Six-Membered Heterocycles with One Nitrogen Atom

5.1 Piperidine and Pyridine Derivatives

5.2 Quinoline and Quinolinone Derivatives

5.3 Isoquinoline Derivatives

6 Synthesis of Six-Membered Heterocycles with Two Nitrogen Atoms

6.1 Quinazoline Derivatives

6.2 Quinazolinone Derivatives

7 Synthesis of N-Fused Heterocycles

8 Summary

Key words

copper catalysis - N-heterocyclic compound - five-membered heterocycle - six-membered heterocycle - N-fused heterocycle

• References

• 1 DeSimone RW, Currie KS, Mitchell SA, Darrow JW, Pippin DA. Comb. Chem. High Throughput Screening 2004; 7: 473
• 2 Leeson PD, Springthorpe B. Nat. Rev. Drug Discovery 2007; 6: 881

For recent reviews on copper-catalyzed cross couplings, see:
• 3a Ley SV, Thomas AW. Angew. Chem. Int. Ed. 2003; 42: 5400
• 3b Kunz K, Scholz U, Ganzer D. Synlett 2003; 2428
• 3c Beletskaya IP, Cheprakov AV. Coord. Chem. Rev. 2004; 248: 2337
• 3d Ma D, Cai Q. Acc. Chem. Res. 2008; 41: 1450
• 3e Evano G, Blanchard N, Toumi M. Chem. Rev. 2008; 108: 3054
• 3f Monnier F, Taillefer M. Angew. Chem. Int. Ed. 2009; 48: 6954
• 3g Rao H, Fu H. Synlett 2011; 745 ; and references cited therein

For selected papers, see:
• 4a Klapars A, Antilla JC, Huang X, Buchwald SL. J. Am. Chem. Soc. 2001; 123: 7727
• 4b Klapars A, Huang XH, Buchwald SL. J. Am. Chem. Soc. 2002; 124: 7421
• 4c Antilla JC, Klapars A, Buchwald SL. J. Am. Chem. Soc. 2002; 124: 11684
• 4d Okano K, Tokuyama H, Fukuyama T. Org. Lett. 2003; 5: 4987
• 4e Gujadhur RK, Bates CG, Venkataraman D. Org. Lett. 2001; 3: 4315
• 4f Gajare AS, Toyota K, Yoshifuji M, Yoshifuji F. Chem. Commun. 2004; 1994
• 4g Ma D, Zhang Y, Yao J, Wu S, Tao F. J. Am. Chem. Soc. 1998; 120: 12459
• 4h Ma D, Cai Q, Zhang H. Org. Lett. 2003; 5: 2453
• 4i Zhu L, Cheng L, Zhang Y, Xie R, You J. J. Org. Chem. 2007; 72: 2737
• 4j Rao H, Jin Y, Fu H, Jiang Y, Zhao Y. Chem.–Eur. J. 2006; 12: 3636
• 5 Hall JA. Bioorg. Med. Chem. Lett. 2007; 17: 1200
• 6a Bellina F, Rossi R. Tetrahedron 2006; 62: 7213
• 6b Butler MS. J. Nat. Prod. 2004; 67: 2141
• 6c Higgins S. Chem. Soc. Rev. 1997; 26: 247
• 7a Dalko PI, Moisan L. Angew. Chem. Int. Ed. 2004; 43: 5138
• 7b Asymmetric Organocatalysis. Berkessel A, Gröber H. Wiley-VCH; Weinheim: 2005
• 8 Lehn JM. Supramolecular Chemistry: Concepts and Perspectives. VCH; Weinheim: 1995
• 9 Han J, Xu B, Hammond GB. J. Am. Chem. Soc. 2010; 132: 916
• 10 Garner P, Hu J, Parker CG, Youngs WJ, Medvetz D. Tetrahedron Lett. 2007; 48: 3867
• 11 Galliford CV, Martenson JS, Stern C, Scheidt KA. Chem. Commun. 2007; 631
• 12 Kuchibe K, Hatemata R, Akiyama T. Tetrahedron 2006; 62: 11304
• 13 Larionov O, de Meijere A. Angew. Chem. Int. Ed. 2005; 44: 5664
• 14 Kamijo S, Kanazawa C, Yamamoto Y. J. Am. Chem. Soc. 2005; 127: 9260
• 15 Brichacek M, Villalobos MN, Plichta A, Njardarson JT. Org. Lett. 2011; 13: 1110
• 16 Martin R, Larsen CH, Cuenca A, Buchwald SL. Org. Lett. 2007; 9: 3379
• 17 Yuan X, Xu X, Zhou X, Yuan J, Mai L, Li Y. J. Org. Chem. 2007; 72: 1510
• 18 Lourdusamy E, Yao L, Park CM. Angew. Chem. Int. Ed. 2010; 49: 7963
• 19 Hong D, Zhu Y, Li Y, Lin X, Lu P, Wang Y. Org. Lett. 2011; 13: 4668
• 20 Yan R, Luo J, Wang C, Ma C, Huang G, Liang Y. J. Org. Chem. 2010; 75: 5395
• 21 Toh K, Wang Y, Ng E, Chiba S. J. Am. Chem. Soc. 2011; 133: 13942
• 22 Gul W, Hamann MT. Life Sci. 2005; 78: 442
• 23 Smart BP, Oslund RC, Walsh LA, Gelb MH. J. Med. Chem. 2006; 49: 2858 ; and references cited therein
• 24 Dandia A, Singh R, Khaturia S, Merienne C, Morgant G, Loupy A. Bioorg. Med. Chem. 2006; 14: 2409 ; and references cited therein
• 25a Mezlova M, Aaron JJ, Svoboda J, Adenier A, Maurel F, Chane-Ching K. J. Electroanal. Chem. 2005; 581: 93
• 25b Janicki SZ, Schuster GB. J. Am. Chem. Soc. 1995; 117: 8524
• 26 Clark GS. Perfum. Flavor. 1995; 20: 21
• 27a Patil S, Buolamwini JK. Curr. Org. Synth. 2006; 3: 477
• 27b Humphrey GR, Kuethe JT. Chem. Rev. 2006; 106: 2875
• 28 Melkonyan F, Topolyan A, Yurovskaya M, Karchava A. Eur. J. Org. Chem. 2008; 5952
• 29 Hodgkinson RC, Schulzb J, Willis MC. Org. Biomol. Chem. 2009; 7: 432
• 30 Wang Z, Yang F, Lv X, Bao W. J. Org. Chem. 2011; 76: 967
• 31 Tanimori S, Ura H, Kirihata M. Eur. J. Org. Chem. 2007; 3977
• 32 Cai Q, Li Z, Wei J, Ha C, Pei D, Ding K. Chem. Commun. 2009; 7581
• 33 Ackermann L, Barfuber S, Potukuchi HK. Adv. Synth. Catal. 2009; 351: 1064
• 34 Hiroya K, Itoh S, Sakamoto T. J. Org. Chem. 2004; 69: 1126
• 35 Chen Z, Zheng D, Wu J. Org. Lett. 2011; 13: 848
• 36 Ohta Y, Chiba H, Oishi S, Fujii N, Ohno H. J. Org. Chem. 2009; 74: 7052
• 37 Chernyak D, Chernyak N, Gevorgyan V. Adv. Synth. Catal. 2010; 352: 961
• 38 Tobisu M, Fujihara H, Kou K, Chatani N. J. Org. Chem. 2010; 75: 4841
• 39 Bernini R, Fabrizi G, Sferrazza A, Cacchi S. Angew. Chem. Int. Ed. 2009; 48: 8078
• 40 Botero CidH. M, Trankle C, Baumann K, Pick R, Mies-Klomfass E, Kostenis E, Mohr K, Holzgrabe U. J. Med. Chem. 2000; 43: 2155
• 41 Parkes KE. B, Ermert P, Fassler J, Ives J, Martin JA, Merrett JH, Obrecht D, Williams G, Klumpp K. J. Med. Chem. 2003; 46: 1153
• 42 Couty S, Meyer C, Cossy J. Tetrahedron Lett. 2006; 47: 767
• 43 Itoh J, Han SB, Krische MJ. Angew. Chem. Int. Ed. 2009; 48: 6313
• 44 Lu B, Ma D. Org. Lett. 2006; 8: 6115
• 45 Yoo EJ, Chang S. Org. Lett. 2008; 10: 1163
• 46 Tang B, Song R, Wu C, Liu Y, Zhou M, Wei W, Deng G, Yin D, Li J. J. Am. Chem. Soc. 2010; 132: 8900
• 47 Klein JE. M. N, Perry A, Pugh DS, Taylor RJ. K. Org. Lett. 2010; 12: 3446
• 48 Li L, Wang M, Zhang X, Jiang Y, Ma D. Org. Lett. 2009; 11: 1309
• 49 Collini MD, Miller CP, Dinh T, Henderson RA, Keith JC. Jr, Harris HA. J. Med. Chem. 2004; 47: 5021
• 50 Sun L.-Q, Chen J, Takaki K, Johnson G, Iben L, Mahle CD, Ryan E, Xu C. Bioorg. Med. Chem. Lett. 2004; 14: 1197
• 51 Yoshida S, Shiokawa S, Kawano K, Ito T, Murakami H, Suzuki H, Sato Y. J. Med. Chem. 2005; 48: 7075
• 52 Tanaka K, Kumagai T, Aoki H, Deguchi M, Iwata S. J. Org. Chem. 2001; 66: 7328
• 53 Wu C, Tsay P, Cheng H, Bai S. J. Appl. Phys. 2004; 95: 417
• 54 Zhang L, Fan J, Vu K, Hong K, Le Brazidec J.-Y, Shi J, Biamonte M, Busch DJ, Lough RE, Grecko R, Ran Y, Sensintaffar JL, Kamal A, Lundgren K, Burrows FJ, Mansfield R, Timony GA, Ulm EH, Kasibhatla SR, Boehm MF. J. Med. Chem. 2006; 40: 5352
• 55 Dumas J, Brittelli D, Chen J, Dixon B, Hatoum-Mokdad H, Konig G, Sibley R, Witowsky J, Wong S. Bioorg. Med. Chem. Lett. 1999; 9: 2531
• 56 Cicchi S, Cordero FM, Giomi D. Prog. Heterocycl. Chem. 2003; 15: 261
• 57 Cano I, Alvarez E, Nicasio MC, Perez PJ. J. Am. Chem. Soc. 2011; 133: 191
• 58 Hansen T, Wu P, Fokin V. J. Org. Chem. 2005; 70: 7761
• 59 Evindar G, Batey RA. J. Org. Chem. 2006; 71: 1802
• 60 Barbero N, Carril M, Sanmartin R, Dominguez E. Tetrahedron 2007; 63: 10425
• 61 Saha P, Ramana T, Purkait N, Ali MA, Paul R, Punniyamurthy T. J. Org. Chem. 2009; 74: 8719
• 62 Xu D, Xu X, Liu Z, Sun L, You Q. Synlett 2009; 1172
• 63 Altenhoff G, Glorius F. Adv. Synth. Catal. 2004; 346: 1661
• 64 Murru S, Ghosh H, Sahoo SK, Patel BK. Org. Lett. 2009; 11: 4254
• 65 Pi S, Zhang X, Tang R, Li J. Synlett 2009; 3032
• 66 Shen G, Bao W. Adv. Synth. Catal. 2010; 352: 981
• 67 Wang F, Cai S, Liao Q, Xi C. J. Org. Chem. 2011; 76: 3174
• 68 Ueda S, Nagasawa H. Angew. Chem. Int. Ed. 2008; 47: 6411
• 69 Ueda S, Nagasawa H. J. Org. Chem. 2009; 74: 4272
• 70 Guru MM, Ali MA, Punniyamurthy T. Org. Lett. 2011; 13: 1194
• 71 Britton R, Roberge M, Berisch H, Andersen RJ. Tetrahedron Lett. 2001; 42: 2953
• 72 Ciminiello P, Aversano CD, Fattorusso E, Magno S. J. Org. Chem. 2001; 1: 55
• 73 Ishida K, Nakagawa H, Murakami M. J. Nat. Prod. 2000; 63: 1315
• 74 Kanazawa C, Kamijo S, Ymamoto Y. J. Am. Chem. Soc. 2006; 128: 10662
• 75 Bonin MA, Giguere D, Roy R. Tetrahedron 2007; 63: 4912
• 76 Battershill AJ, Scott LJ. Drugs 2006; 66: 51
• 77 Hirashima S, Suzuki T, Ishida T, Noji S, Yata S, Ando I, Komatsu M, Ikeda S, Hashimoto H. J. Med. Chem. 2006; 49: 4721
• 78 Hauel NH, Nar H, Priepke H, Ries U, Stassen J, Wienen W. J. Med. Chem. 2002; 45: 1757
• 79 Nakano H, Inoue T, Kawasaki N, Miyataka H, Matsumoto H, Taguchi T, Inagaki N, Nagai H, Satoh T. Bioorg. Med. Chem. 2000; 8: 373
• 80 Murru S, Patel BK, Le Bras J, Muzart J. J. Org. Chem. 2009; 74: 2217
• 81 Hirano K, Biju AT, Glorius F. J. Org. Chem. 2009; 74: 9570
• 82 Lv X, Bao W. J. Org. Chem. 2009; 74: 5618
• 83 Lygin AV, de Meijere A. Eur. J. Org. Chem. 2009; 5138
• 84 Zhu J, Xie H, Chen Z, Li S, Wu Y. Chem. Commun. 2009; 2338
• 85 Yang D, Fu H, Hu L, Jiang Y, Zhao Y. J. Org. Chem. 2008; 73: 7841
• 86 Zou B, Yuan Q, Ma D. Angew. Chem. Int. Ed. 2007; 46: 2598
• 87 Diao X, Wang Y, Jiang Y, Ma D. J. Org. Chem. 2009; 74: 7974
• 88 Zheng N, Buchwald SL. Org. Lett. 2007; 9: 4749
• 89 Brasche G, Buchwald SL. Angew. Chem. Int. Ed. 2008; 47: 1932
• 90 Deng X, McAllister H, Mani NS. J. Org. Chem. 2009; 74: 5742
• 91 Barreca ML, Rao A, De Luca L, Iraci N, Monforte A.-M, Maga G, De Clercq E, Pannecouque C, Balzarini J, Chimirri A. Bioorg. Med. Chem. Lett. 2007; 17: 1956
• 92 Calderone V, Coi A, Fiamingo FL, Giorgi I, Leonardo M, Livi O, Martelli A, Martinotti E. Eur. J. Med. Chem. 2006; 41: 1421
• 93 Terefenko EA, Kern J, Fensome A, Wrobel J, Zhu Y, Cohen J, Winneker R, Zhang Z, Zhang P. Bioorg. Med. Chem. Lett. 2005; 15: 3600
• 94 Barbero N, Carril M, SanMartin RDominguez E. Tetrahedron 2008; 64: 7283
• 95 Li Z, Sun H, Jiang H, Liu H. Org. Lett. 2008; 10: 3263
• 96 Zou B, Yuan Q, Ma D. Org. Lett. 2007; 9: 4291
• 97 Zhao B, Du H, Shi Y. J. Org. Chem. 2009; 74: 8392
• 98 Butler RN. Comprehensive Heterocyclic Chemistry. Vol. 4. Katritzky AR, Rees CW, Scriven EF. V. Pergamon Press; Oxford: 1996
• 99 Huisgen R. 1,3-Dipolar Cycloaddition Chemistry. Padwa A. Wiley; New York: 1984
• 100 Kolb HC, Finn MG, Sharpless KB. Angew. Chem. Int. Ed. 2001; 40: 2004
• 101a Moses JE, Moorhouse AD. Chem. Soc. Rev. 2007; 36: 1249
• 101b Ganesh V, Sudhir VS, Kundu T, Chandrasekaran S. Chem.–Asian J. 2011; 6: 2670
• 101c Agalave SG, Maujan SR, Pore VS. Chem.–Asian J. 2011; 6: 2696
• 101d Hein JE, Fokin VV. Chem. Soc. Rev. 2010; 39: 1302
• 102 Yoo EJ, Ahlquist M, Kim SH, Bae I, Fokin VV, Sharpless KB, Chang S. Angew. Chem. Int. Ed. 2007; 46: 1730
• 103 Wang F, Fu H, Jiang Y, Zhao Y. Adv. Synth. Catal. 2008; 350: 1830
• 104 Raushel J, Fokin VV. Org. Lett. 2010; 12: 4952
• 105 Wang K, Bi X, Xing S, Liao P, Fang Z, Meng X, Zhang Q, Liu Q, Ji Y. Green Chem. 2011; 13: 562
• 106 Esquivias J, Alonoso I, Arrayás RG, Carretero JC. Synthesis 2009; 113
• 107 Ren Z, Zhang Z, Yang B, Wang Y, Guan Z. Org. Lett. 2011; 13: 5394
• 108 Nakamura I, Zhang D, Terada M. J. Am. Chem. Soc. 2010; 132: 7884
• 109a Fournet A, Mahieux R, Fakhfakh MA, Franck X, Hocquemiller R, Figadere B. Bioorg. Med. Chem. Lett. 2003; 13: 891
• 109b Zwaagstra ME, Timmerman H, van de Stolpe AC, deKanter FJ. J, Tamura M, Wada Y, Zhang M.-Q. J. Med. Chem. 1998; 41: 1428
• 110 Hadjeri M, Peiller E.-L, Beney C, Deka N, Lawson MA, Dumontet C, Boumendjel A. J. Med. Chem. 2004; 47: 4964
• 111 Llinas-Brunet M, Bailey MD, Ghiro E, Gorys V, Halmos T, Poirier M, Rancourt J, Goudreau N. J. Med. Chem. 2004; 47: 6584
• 112 Huang L, Hsieh M, Teng C, Lee K, Kuo S. Bioorg. Med. Chem. 1998; 6: 1657
• 113 Rao WD, Kothandaraman P, Koh CB, Chana PW. H. Adv. Synth. Catal. 2010; 352: 2521
• 114 Patil NT, Raut VS. J. Org. Chem. 2010; 75: 6961
• 115 Li S, Yuan Y, Zhu J, Xie H, Chen Z, Wu Y. Adv. Synth. Catal. 2010; 352: 1582
• 116 Zhang L, Ang GY, Chiba S. Org. Lett. 2010; 12: 3682
• 117 Jones CP, Anderson KW, Buchwald SL. J. Org. Chem. 2007; 72: 7968
• 118a Bisagni E, Jin L, Leclercq G. Bioorg. Med. Chem. 2000; 8: 2629
• 118b Morrel A, Antony S, Kohlhagen G, Pommier Y, Cushman M. J. Med. Chem. 2006; 49: 7740
• 118c Bentley KW. Nat. Prod. Rep. 2005; 22: 249
• 119 Wang B, Lu B, Jiang YW, Zhang YH, Ma D. Org. Lett. 2008; 10: 2761
• 120 Yu X, Ding Q, Chen Z, Wu J. Tetrahedron Lett. 2009; 50: 4279
• 121 Ohta Y, Oishi S, Fujii N, Ohno H. Chem. Commun. 2008; 835
• 122 Ma Z, Hano Y, Nomura T, Chen Y. Heterocycles 1997; 46: 541
• 123 Wattanapiromsakul C, Forster PI, Waterman PG. Phytochemistry 2003; 64: 609
• 124 Witt A Bergman Curr. Org. Chem. 2003; 7: 659 ; and references cited therein
• 125 Mhaske SB, Argade NP. Tetrahedron 2006; 62: 9787 ; and references cited therein
• 126a Huang C, Fu Y, Fu H, Jiang Y, Zhao Y. Chem. Commun. 2008; 6333
• 126b Huang X, Yang H, Fu H, Qiao R, Zhao Y. Synthesis 2009; 2679
• 127 Yang X, Liu H, Fu H, Qiao R, Jiang Y, Zhao Y. Synlett 2010; 101
• 128 Truong VL, Morrow M. Tetrahedron Lett. 2010; 51: 758
• 129 Ohta Y, Tokimizu Y, Oishi S, Fujii N, Ohno H. Org. Lett. 2010; 12: 3963
• 130 Wang C, Li S, Liu H, Jiang Y, Fu H. J. Org. Chem. 2010; 75: 7936
• 131 Zhang J, Yu C, Wang S, Wan C, Wang Z. Chem. Commun. 2010; 46: 5244
• 132 Liu X, Fu H, Jiang Y, Zhao Y. Angew. Chem. Int. Ed. 2009; 48: 348
• 133 Cai Q, Li Z, Wei J, Fu L, Pei D, Ding K. Org. Lett. 2010; 12: 1500
• 134 Xu H, Zhang Y, Huang J, Chen W. Org. Lett. 2010; 12: 3704
• 135 Yadav JS, Subbareddy BV, Rao YG, Srinivas M, Narsaiah AV. Tetrahedron Lett. 2007; 48: 7717
• 136 Barluenga J, Lonzi G, Riesgo L, Lopez LA, Tomas M. J. Am. Chem. Soc. 2010; 132: 13200
• 137 Ouyang H, Tang R, Zhong P, Zhang X, Li J. J. Org. Chem. 2011; 76: 223
• 138 Kel’in AV, Sromek AW, Gevorgyan V. J. Am. Chem. Soc. 2001; 123: 2074
• 139 Yan B, Zhou Y, Zhang H, Chen J, Liu Y. J. Org. Chem. 2007; 72: 7783
• 140 Ohta Y, Kubota Y, Watabe T, Chiba H, Oishi S, Fujii N, Ohno H. J. Org. Chem. 2009; 74: 6299
• 141 Lu J, Gong X, Yang H, Fu H. Chem. Commun. 2010; 46: 4172
• 142 Lu J, Fu H. J. Org. Chem. 2011; 76: 4600
• 143 Liu T, Wang R, Yang H, Fu H. Chem.–Eur. J. 2011; 17: 6765