Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2018; 50(02): 361-370
DOI: 10.1055/s-0036-1588585
DOI: 10.1055/s-0036-1588585
paper
Copper-Catalyzed Simultaneous Activation of C–H and N–H Bonds: Three-Component One-Pot Cascade Synthesis of Multisubstituted Imidazoles
Further Information
Publication History
Received: 11 September 2017
Accepted after revision: 12 September 2017
Publication Date:
10 October 2017 (online)
§ Authors contributed equally to this work.
Abstract
A copper-catalyzed expedient, practical, and straightforward approach for the one-pot three-component modular synthesis of multisubstituted imidazoles has been described by using arylacetic acids, N-arylbenzamidines, and nitroalkanes. The reaction involves simultaneous activation of C–H and N–H bonds of arylacetic acids and N-arylbenzamidines, respectively. The use of inexpensive copper sulfate as a catalyst, readily available starting materials, and Celite-free workup makes this protocol economically viable. Multisubstituted imidazoles were obtained in moderate to good yields with significant functional group tolerance and high regioselectivity.
Key words
arylacetic acid - N-arylbenzamidine - C–H bond activation - N–H bond activation - CuSO4 - imidazoleSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1588585.
- Supporting Information
-
References
- 1a Tietze LF. Brasche G. Gericke K. Domino Reactions in Organic Synthesis. Wiley-VCH; Weinheim: 2006
- 1b Zhu JP. Bienaym H. Multicomponent Reactions . Wiley-VCH; Weinheim: 2005
- 1c Tietze LF. Chem. Rev. 1996; 96: 115
- 1d Nicolaou KC. Montagnon T. Snyder SA. Chem. Commun. 2003; 551
- 1e Padwa A. Bur SK. Tetrahedron 2007; 63: 5341
- 1f Shindoh N. Takemoto Y. Takasu K. Chem. Eur. J. 2009; 15: 12168
- 2a Tietze LF. Brasche G. Gericke K. Domino Reactions in Organic Synthesis . Wiley-VCH; Weinheim: 2014
- 2b Pellissier H. Chem. Rev. 2013; 113: 442
- 2c Tietze LF. Kinzel T. Brazel CC. Acc. Chem. Res. 2009; 42: 367
- 2d Tietze LF. Rackelmann N. Pure Appl. Chem. 2004; 76: 1967
- 3a Jin Z. Nat. Prod. Rep. 2009; 26: 382
- 3b Forte B. Malgesini B. Piutti C. Quartieri F. Scolaro A. Papeo G. Mar. Drugs 2009; 7: 705
- 3c Midoux P. Pichon C. Yaouanc J.-J. Jaffrès P.-A. Br. J. Pharmacol. 2009; 157: 166
- 3d Xiong F. Chen X.-X. Chen F.-E. Tetrahedron: Asymmetry 2010; 21: 665
- 4a Lee JC. Laydon JT. McDonnell PC. Gallagher TF. Kumar S. Green D. McNulty D. Blumenthal MJ. Heys JR. Landvatter SW. Strickler JE. McLaughlin MM. Siemens IR. Fisher SM. Livi GP. White JR. Adams JL. Young PR. Nature (London) 1994; 372: 739
- 4b de Laszlo SE. Hacker C. Li B. Kim D. MacCoss M. Mantlo N. Pivnichny JV. Colwell L. Koch GE. Cascieri MA. Hagmann WK. Bioorg. Med. Chem. Lett. 1999; 9: 641
- 4c Antolini M. Bozzoli A. Ghiron C. Kennedy G. Rossi T. Ursini A. Bioorg. Med. Chem. Lett. 1999; 9: 1023
- 4d Wang L. Woods KW. Li Q. Barr KJ. McCroskey RW. Hannick SM. Gherke L. Credo RB. Hui Y.-H. Marsh K. Warner R. Lee JY. Zielinski-Mozng N. Frost D. Rosenberg SH. Sham HL. J. Med. Chem. 2002; 45: 1697
- 4e Dietrich J. Gokhale V. Wang X. Hurley LH. Flynn GA. Bioorg. Med. Chem. 2010; 18: 292
- 4f Cho HJ. Gee HY. Baek K.-H. Ko S.-K. Park J.-M. Lee H. Kim N.-D. Lee MG. Shin I. J. Am. Chem. Soc. 2011; 133: 20267
- 5a Bonezzi K. Taraboletti G. Borsotti P. Bellina F. Rossi R. Giavazzi R. J. Med. Chem. 2009; 52: 7906
- 5b Sadek B. Pharma Chem. 2011; 3: 410
- 5c Jin CH. Krishnaiah M. Sreenu D. Subrahmanyam VB. Rao KS. Lee HJ. Park SJ. Park HJ. Lee K. Sheen YY. Kim DK. J. Med. Chem. 2014; 57: 4213
- 5d Zhang L. Peng X.-M. Damu GL. V. Geng R.-X. Zhou C.-H. Med. Res. Rev. 2014; 34: 340
- 6a Wolff DJ. Datto GA. Samatovicz RA. J. Biol. Chem. 1993; 268: 9430
- 6b Sennequier N. Wolan D. Stuehr DJ. J. Biol. Chem. 1999; 274: 930
- 6c Koga H. Nanjoh Y. Makimura K. Tsuboi R. Med. Mycol. 2009; 47: 640
- 6d Röhrig UF. Majjigapu SR. Chambon M. Bron S. Pilotte L. Colau D. Van den Eynde BJ. Turcatti G. Vogel P. Zoete V. Michielin O. Eur. J. Med. Chem. 2014; 84: 284
- 7a Fukui M. Inaba M. Tsukagoshi S. Sakural Y. Cancer Res. 1982; 42: 1098
- 7b Atwell GJ. Fan J.-Y. Tan K. Denny WA. J. Med. Chem. 1998; 41: 4744
- 7c Al-Raqa SY. ElSharief AM. S. Khalil SM. E. Al-Amri AM. Heteroat. Chem. 2006; 17: 634
- 8a Vijesh AM. Isloor AM. Telkar S. Peethambar SK. Rai S. Isloor N. Eur. J. Med. Chem. 2011; 46: 3531
- 8b Choi JY. Plummer MS. Starr J. Desbonnet CR. Soutter H. Chang J. Miller JR. Dillman K. Miller AA. Roush WR. J. Med. Chem. 2012; 55: 852
- 8c Yurttaş L. Duran M. Demirayak Ş. Gençer HK. Tunalı Y. Bioorg. Med. Chem. Lett. 2013; 23: 6764
- 9 Vlahakis JZ. Lazar C. Crandall IE. Szarek WA. Bioorg. Med. Chem. 2010; 18: 6184
- 10a Adams JL. Boehm JC. Gallagher TF. Kassis S. Webb EF. Hall R. Sorenson M. Garigipati R. Griswold DE. Lee JC. Bioorg. Med. Chem. Lett. 2001; 11: 2867
- 10b Husain A. Drabu S. Kumar N. Alam MM. Bawa S. J. Pharm. BioAllied Sci. 2013; 5: 154
- 11a Maeda Y. Nishimura T. Uemura S. Bull. Chem. Soc. Jpn. 2003; 76: 2399
- 11b Asensio JA. Gómez-Romero P. Fuel Cells 2005; 5: 336
- 11c Singh N. Jang DO. Org. Lett. 2007; 9: 1991
- 11d Nagarajan N. Velmurugan G. Prakash A. Shakti N. Katiyar M. Venuvanalingam P. Renganathan R. Chem. Asian J. 2014; 9: 294
- 11e Kwon JE. Park S. Park SY. J. Am. Chem. Soc. 2013; 135: 11239
- 11f Yuan Y. Chen J.-X. Lu F. Tong Q.-X. Yang Q.-D. Mo H.-W. Ng T.-W. Wong F.-L. Guo Z.-Q. Ye J. Chen Z. Zhang X.-H. Lee C.-S. Chem. Mater. 2013; 25: 4957
- 11g Jeżewski A. Hammann T. Cywiński PJ. Gryko DT. J. Phys. Chem. B 2015; 119: 2507
- 12a Mowry DT. Chem. Rev. 1948; 42: 189
- 12b Ellis GP. Romney-Alexander TM. Chem. Rev. 1987; 87: 779
- 12c Bacon RG. R. Hill HA. O. J. Chem. Soc. 1964; 1097
- 12d Sandmeyer T. Ber. Dtsch. Chem. Ges. 1884; 17: 2650
- 12e Koelsch CF. Whitney AG. J. Org. Chem. 1941; 6: 795
- 13a Mori K. Yamaguchi K. Mizugaki T. Ebitani K. Kaneda K. Chem. Commun. 2001; 461
- 13b Yamaguchi K. Mizuno N. Angew. Chem. Int. Ed. 2003; 42: 1480
- 13c Kotani M. Koike T. Yamaguchi K. Mizuno N. Green Chem. 2006; 8: 735
- 13d Li F. Chen J. Zhang Q. Wang Y. Green Chem. 2008; 10: 553
- 13e Zhang Y. Xu K. Chen X. Hu T. Yu Y. Zhang J. Huang J. Catal. Commun. 2010; 11: 951
- 14a Capdevielle P. Lavigne A. Sparfel D. Baranne-Lafont J. Nguyen KC. Maumy M. Tetrahedron Lett. 1990; 31: 3305
- 14b Tang R. Diamond SE. Neary N. Mares F. J. Chem. Soc., Chem. Commun. 1978; 562
- 14c Porta F. Crotti C. Cennini S. J. Mol. Catal. 1989; 50: 333
- 14d Bailey AJ. James BR. Chem. Commun. 1996; 2343
- 15 Kison C. Opatz T. Chem. Eur. J. 2009; 15: 843
- 16 Hu B. Wang Z. Ai N. Zheng J. Liu X.-H. Shan S. Wang Z. Org. Lett. 2011; 13: 6362
- 17a Tang D. Wu P. Liu X. Chen Y.-X. Guo S.-B. Chen W.-L. Li J.-G. Chen B.-H. J. Org. Chem. 2013; 78: 2746
- 17b Liu X. Wang D. Chen B. Tetrahedron 2013; 69: 9417
- 17c Mitra S. Bagdi AK. Majee A. Hajra A. Tetrahedron Lett. 2013; 54: 4982
- 17d Kumar T. Verma D. Menna-Barreto RF. S. Valença WO. da Silva Júnior EN. Namboothiri IN. N. Org. Biomol. Chem. 2015; 13: 1996
- 18a Nie Y.-B. Wang L. Ding M.-W. J. Org. Chem. 2012; 77: 696
- 18b Jiang Z. Lu P. Wang Y. Org. Lett. 2012; 14: 6266
- 18c Liu X. Wang D. Chen Y. Tang D. Chen B. Adv. Synth. Catal. 2013; 355: 2798
- 18d Chen C.-Y. Hu W.-P. Yan P.-C. Senadi GC. Wang J.-J. Org. Lett. 2013; 15: 6116
- 18e Pusch S. Opatz T. Org. Lett. 2014; 16: 5430
- 18f Aly S. Romashko M. Arndtsen BA. J. Org. Chem. 2015; 80: 2709
- 19 Tlahuext-Aca A. Hernández-Fajardo O. Arévalo A. García JJ. Dalton Trans. 2014; 43: 15997
- 20 Cardoso AL. Lemos A. Pinho e Melo TM. V. D. Eur. J. Org. Chem. 2014; 5159
- 21 Chen H. Chiba S. Org. Biomol. Chem. 2014; 12: 42
- 22 Adib M. Ansari S. Feizi S. Damavandi JA. Mirzaei P. Synlett 2009; 3263
- 23 Auricchio S. Truscello AM. Lauria M. Meille SV. Tetrahedron 2012; 68: 7441
- 24 Qu J. Wu P. Tang D. Meng X. Chen Y. Guo S. Chen B. New J. Chem. 2015; 39: 4235
- 25 Hota PK. Vijaykumar G. Pariyar A. Sau SC. Sen TK. Mandal SK. Adv. Synth. Catal. 2015; 357: 3162
- 26 Li J. Neuville L. Org. Lett. 2013; 15: 1752
- 27 Sharma AK. Mazumdar SN. Mahajan MP. J. Chem. Soc., Perkin Trans. 1 1997; 3065
- 28a Zhou X. Ma H. Shi C. Zhang Y. Liu X. Huang G. Eur. J. Org. Chem. 2017; 237
- 28b Zhu Y. Li C. Zhang J. She M. Sun W. Wan K. Wang Y. Yin B. Liu P. Li J. Org. Lett. 2015; 17: 3872
- 29a Kalmode HP. Vadagaonkar KS. Murugan K. Chaskar AC. New J. Chem. 2015; 39: 4631
- 29b Kalmode HP. Vadagaonkar KS. Murugan K. Prakash S. Chaskar AC. RSC Adv. 2015; 5: 35166
- 29c Vadagaonkar KS. Kalmode HP. Prakash S. Chaskar AC. New J. Chem. 2015; 39: 3639
- 29d Vadagaonkar KS. Kalmode HP. Murugan K. Chaskar AC. RSC Adv. 2015; 5: 5580
- 29e Vadagaonkar KS. Murugan K. Chaskar AC. Bhate PM. RSC Adv. 2014; 4: 34056
- 30 Chen X. Chen T. Ji F. Zhou Y. Yin S.-F. Catal. Sci. Technol. 2015; 5: 2197
- 31 Yang D. Yan K. Wei W. Tian L. Shuai Y. Li R. You J. Wang H. Asian J. Org. Chem. 2014; 3: 969
- 32 Gandeepan P. Rajamalli P. Cheng C.-H. Asian J. Org. Chem. 2014; 3: 303
- 33 Mahmudov KT. Kopylovich MN. Haukka M. Mahmudova GS. Esmaeila EF. Chyragov FM. Pombeiro AJ. L. J. Mol. Struct. 2013; 1048: 108
- 34 Jalal S. Sarkar S. Bera K. Maiti S. Jana U. Eur. J. Org. Chem. 2013; 4823
- 35 Maiti S. Biswas S. Jana U. J. Org. Chem. 2010; 75: 1674
- 36 Cooper FC. Partridge MW. Org. Synth. 1956; 36: 64
- 37 Tang D. Guo X. Wang Y. Wang J. Li J. Huang Q. Chen B. Tetrahedron Lett. 2015; 56: 5982
- 38 Gopi E. Kumar T. Menna-Barreto RF. S. Valença WO. da Silva Júnior EN. Namboothiri IN. N. Org. Biomol. Chem. 2015; 13: 9862
- 39 Zuliani V. Cocconcelli G. Fantini M. Ghiron C. Rivara M. J. Org. Chem. 2007; 72: 4551