DABCO-Promoted [3+2] Annulation for Efficient Synthesis of 1,2,5-Triaryl-1H-imidazoles from Substituted β-Nitrostyrenes and N-Arylbenzimidamides

Abstract

An efficient approach to the synthesis of 1,2,5-trisubstituted imidazole derivatives was investigated via a DABCO-promoted formal [3+2]-annulation reaction of substituted N-arylbenzimidamides and substituted β-nitrostyrenes. The annulation reaction is implemented easily to afford the corresponding products in moderate to good yields with excellent regioselectivity.

Key words

1,2,5-trisubstituted imidazoles - [3+2] annulation - cyclo­addition - N-arylbenzimidamides - β-nitrostyrenes

Publication History

Received: 28 April 2021

Accepted after revision: 22 June 2021

Accepted Manuscript online:
22 June 2021

Article published online:
05 August 2021

• References

• 1a Mohanty I, Moore SG, Yi D, Biggs JS, Gaul DA, Garg N, Agarwal V. ACS Chem. Biol. 2020; 15: 2185
• 1b Miguel-Gordo M, Gegunde S, Jennings LK, Genta-Jouve G, Calabro K, Alfonso A, Botana LM, Thomas OP. J. Nat. Prod. 2020; 83: 2299
• 1c Khushi S, Nahar L, Salim AA, Capon RJ. Aust. J. Chem. 2020; 73: 338
• 1d Ul Karim MR, Harunari E, Oku N, Akasaka K, Igarashi Y. J. Nat. Prod. 2020; 83: 1295
• 1e Roue M, Domart-Coulon I, Ereskovsky A, Djediat C, Perez T, Bourguet-Kondracki ML. J. Nat. Prod. 2010; 73: 1277
• 1f Singha Roy M, Meng X, Koda K, Rasapalli S, Gout D, Lovely CJ. Tetrahedron Lett. 2019; 60: 979
• 1g An B, Yin F, de Voogd NJ, Chen X, Cheng W, Lin W. Chem. Biodiversity 2018; 15: e1700481
• 2a Floresta G, Amata E, Gentile D, Romeo G, Marrazzo A, Pittala V, Salerno L, Rescifina A. Mar. Drugs 2019; 17: 113
• 2b Kwapong AA, Stapleton P, Gibbons S. Tetrahedron Lett. 2018; 59: 1952
• 2c Rodrigues de Carvalho L, Vieira de Brito T, Simião da C Júnior J, Dias Júnior GJ, de Aguiar Magalhãres D, Guimarães Sousa S, Oliveira Silva R, Pereira da Silva FR, Pereira Vasconcelos DF, Costa Véras LM, de Sousa de Almeida Leite JR, Santos Martins D, da Silva Martins C, Soares de Oliveira J, dos Reis Barbosa AL. Biomed. Pharmacother. 2018; 102: 278
• 2d Nicolau LA. D, Carvalho NS, Pacífico DM, Lucetti LT, Aragão KS, Véras LM. C, Souza MH. L. P, Leite JR. S. A, Medeiros JV. R. Biomed. Pharmacother. 2017; 87: 188
• 2e Juchum M, Günther M, Doering E, Sievers-Engler A, Lämmerhofer M, Laufer SA. J. Med. Chem. 2017; 60: 4636
• 2f Wiglenda T, Gust R. J. Med. Chem. 2007; 50: 1475
• 2g Xiao M, Ahn S, Wang J, Chen J, Miller DD, Dalton JT, Li W. J. Med. Chem. 2013; 56: 3318
• 2h Breslin HJ, Miskowski TA, Rafferty BM, Coutinho SV, Palmer JM, Wallace NH, Schneider CR, Kimball ES, Zhang S.-P, Li J, Colburn RW, Stone DJ, Martinez RP, He W. J. Med. Chem. 2004; 47: 5009
• 3a Wen SQ, Jeyakkumar P, Avula SR, Zhang L, Zhou CH. Bioorg. Med. Chem. Lett. 2016; 26: 2768
• 3b Ammar YA, El-Sharief MA, Ghorab MM, Mohamed YA, Ragab A, Abbas SY. Curr. Org. Synth. 2016; 13: 466
• 4a Liu H.-B, Lauro G, O’Connor RD, Lohith K, Kelly M, Colin P, Bifulco G, Bewley CA. J. Nat. Prod. 2017; 80: 2556
• 4b Rocha JA, Andrade IM, Veras LM. C, Quelemes PV, Lima DF, Soares MJ. S, Pinto PL. S, Mayo SJ, Ivanova G, Rangel M. Phytother. Res. 2017; 31: 624
• 5a Negi A, Murphy PV. Eur. J. Med. Chem. 2021; 210: 113038
• 5b Gu W, Miao T.-T, Hua D.-W, Jin X.-Y, Tao X.-B, Huang C.-B, Wang S.-F. Bioorg. Med. Chem. Lett. 2017; 27: 1296
• 5c Subramanian S, Yang H.-S, Manickam M, Yun J, Jung S.-H. Bull. Korean Chem. Soc. 2016; 37: 632
• 5d Yong J, Lu C, Wu X. Lett. Org. Chem. 2016; 13: 283
• 6 Bendjeddou LZ, Loaec N, Villiers B, Prina E, Spath GF, Galons H, Meijer L, Oumata N. Eur. J. Med. Chem. 2017; 125: 696
• 7 Hanumantha Rao B, Subramanyeswara Rao IV, Ravi Kanth V, Prasada Rao KV. V, Balamurali Krishna K, Syama Sundar B. Sci. Pharm. 2015; 83: 465
• 8 Osei E, Kwain S, Mawuli GT, Anang AK, Owusu KB.-A, Camas M, Camas AS, Ohashi M, Alexandru-Crivac C.-N, Deng H. Mar. Drugs 2019; 17: 9
• 9a Ghorbani-Vaghei R, Izadkhah V, Mahmoodi J, Karamian R, Ahmadi Khoei M. Monatsh. Chem. 2018; 149: 1447
• 9b Naik N, Kumar HV, Rangaswamy J, Harini ST, Umeshkumar TC. J. Appl. Pharm. Sci. 2012; 2: 67
• 10 Huang L, Huang H, Xie Y, He K, Deng J. CN112047887A, 2020
• 11 Li J, Zheng X, Bai X, Wang F, Xia X, Chen Q, Li Q, Jia X, Chen J, Wang M. CN112441981A, 2021
• 12a Liu W, Zhang H, Zhang W, Wang M, Li J, Zhang Y, Li H. J. Mater. Sci. 2020; 55: 15275
• 12b Hariharan A, Srinivasan K, Murthy C, Alagar M. Ind. Eng. Chem. Res. 2017; 56: 9347
• 12c Chiang TH, Lin Y.-C, Chen Y.-F, Chen E.-Y. J. Appl. Polym. Sci. 2016; 133: 43587
• 12d Huang JJ, Hung YH, Ting PL, Tsai YN, Gao HJ, Chiu TL, Lee JH, Chen CL, Chou PT, Leung MK. Org. Lett. 2016; 18: 672
• 12e Nagarajan N, Velmurugan G, Prakash A, Shakti N, Katiyar M, Venuvanalingam P, Renganathan R. Chem. Asian J. 2014; 9: 294
• 12f 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
• 13a Zhang X, Gao L, Niu L, Bi X. New J. Chem. 2021; 45: 5195
• 13b Kartsova L, Moskvichev D, Bessonova E, Peshkova M. Chromatographia 2020; 83: 1001
• 13c Cheng Y, Yu S, Xue F. ACS Omega 2020; 5: 8962
• 13d Wang X, Li G, Row KH. J. Sep. Sci. 2017; 40: 3301
• 13e Shaterian HR, Ranjbar M. J. Mol. Liq. 2011; 160: 40
• 13f Dupont J, de Souza RF, Suarez PA. Z. Chem. Rev. 2002; 102: 3667
• 14a Arivunithi VM, Park H.-Y, Reddy SS, Do Y, Park H, Shin E.-S, Noh Y.-Y, Song M, Jin S.-H. Macromol. Res. 2021; 29: 149
• 14b Liu J, Han H, Luo H. CN112251773A, 2021
• 14c Pekdemir F, Orman EB, Selcuki NA, Ozkaya AR, Salih B, Sengul A. J. Photochem. Photobiol., A 2019; 379: 54
• 15a Alic B, Tavcar G. J. Fluorine Chem. 2016; 192: 141
• 15b Hindi KM, Panzner MJ, Tessier CA, Cannon CL, Youngs WJ. Chem. Rev. 2009; 109: 3859
• 15c Hahn FE, Jahnke MC. Angew. Chem. Int. Ed. 2008; 47: 3122
• 15d Hojabri L, Hartikka A, Moghaddam FM, Arvidsson PI. Adv. Synth. Catal. 2007; 349: 740
• 16a Ghorbani-Choghamarani A, Hajjami M, Gholamian F, Azadi G. Russ. J. Org. Chem. 2015; 51: 352
• 16b Karimi-Jaberi Z, Barekat M. Chin. Chem. Lett. 2010; 21: 1183
• 16c Lee S.-H, Yoshida K, Matsushita H, Clapham B, Koch G, Zimmermann J, Janda KD. J. Org. Chem. 2004; 69: 8829
• 17a Liu X, Wang D, Chen Y, Tang D, Chen B. Adv. Synth. Catal. 2013; 355: 2798
• 17b Tang D, Wu P, Liu X, Chen YX, Guo SB, Chen WL, Li JG, Chen BH. J. Org. Chem. 2013; 78: 2746
• 17c Liu X, Wang D, Chen B. Tetrahedron 2013; 69: 9417
• 17d Qu J, Wu P, Tang D, Meng X, Chen Y, Guo S, Chen B. New J. Chem. 2015; 39: 4235
• 17e Adib M, Ansari S, Feizi S, Damavandi J, Mirzaei P. Synlett 2009; 3263
• 17f Hong L, Shao Y, Zhang L, Zhou X. Chem. Eur. J. 2014; 20: 8551
• 17g Cao J, Zhou X, Ma H, Shi C, Huang G. RSC Adv. 2016; 6: 57232
• 17h Li Y, Fu Y, Ren C, Tang D, Wu P, Meng X, Chen B. Org. Chem. Front. 2015; 2: 1632
• 17i Li J, Neuville L. Org. Lett. 2013; 15: 1752
• 18a Guo X, Shao J, Liu H, Chen B, Chen W, Yu Y. RSC Adv. 2015; 5: 51559
• 18b Chen CY, Hu WP, Yan PC, Senadi GC, Wang JJ. Org. Lett. 2013; 15: 6116
• 18c Xu X, Li Y. Res. Chem. Intermed. 2015; 41: 4169
• 18d El Abed D, Adiche C, Hamadouche M. Heterocycles 2016; 92: 1614
• 19a Zhou X, Jiang Z, Xue L, Lu P, Wang Y. Eur. J. Org. Chem. 2015; 5789
• 19b Zhang J, Gao Q, Wu X, Geng X, Wu YD, Wu A. Org. Lett. 2016; 18: 1686
• 19c Sezen B, Sames D. J. Am. Chem. Soc. 2003; 125: 10580
• 19d Katritzky AR, Zhu L, Lang H, Denisko O, Wang Z. Tetrahedron 1995; 51: 13271
• 20a Pivsa-Art S, Satoh T, Kawamura Y, Miura M, Nomura M. Bull. Chem. Soc. Jpn. 1998; 71: 467
• 20b Miura M, Nomura M. Top. Curr. Chem. 2002; 219: 211
• 20c Mori A, Sekiguchi A, Masui K, Shimada T, Horie M, Osakada K, Kawamoto M, Ikeda T. J. Am. Chem. Soc. 2003; 125: 1700
• 20d Li J, Neuville L. Org. Lett. 2013; 15: 6124
• 20e Li J, Benard S, Neuville L, Zhu J. Org. Lett. 2012; 14: 5980
• 20f Navratil R, Tarabek J, Linhart I, Martinu T. Org. Lett. 2016; 18: 3734
• 21a Bellina F, Cauteruccio S, Mannina L, Rossi R, Viel S. Eur. J. Org. Chem. 2006; 693
• 21b Lessi M, Panzetta G, Marianetti G, Bellina F. Synthesis 2017; 49: 4676
• 22a Silva AD. O, McQuade J, Szostak M. Adv. Synth. Catal. 2019; 361: 3050
• 22b Hu F, Szostak M. Adv. Synth. Catal. 2015; 357: 2583
• 22c Zhao X, Guo L, Yang C, Xia W. Synthesis 2021; 53: 1341
• 22d Zhang X.-Z, Qiu Z.-W, Wen G.-H, Ma A.-J, Bao P.-J, Du J.-Y, Xu X.-T, Feng N, Li B.-Q. Synthesis 2020; 52: 3640
• 22e Li J, Xiao J.-A, Zhao S.-J, Xiang H.-Y, Yang H. Synthesis 2017; 49: 4292
• 22f Zheng W, Li Y, Zhang J, Du S, Miao Z. Synthesis 2017; 49: 3676
• 22g Auricchio S, Truscello AM, Lauria M, Meille SV. Tetrahedron 2012; 68: 7441
• 23 Zibinsky M, Fokin VV. Angew. Chem. Int. Ed. 2013; 52: 1507
• 24 Wang J, Zhang F.-D, Tang D, Wu P, Zhang X.-G, Chen B.-H. RSC Adv. 2017; 7: 24594
• 25a Li M, Wang T, Wang C. ChemistrySelect 2020; 5: 3600
• 25b Dai C, Xie Z, Qing X, Luo N, Wang C. Mol. Diversity 2020; 24: 191
• 25c Sun J, Jiang W, Yan C.-G. Org. Chem. Front. 2019; 6: 1428
• 25d Cai Q, Li D.-K, Zhou R.-R, Shu W.-M, Wu Y.-D, Wu A.-X. Org. Lett. 2016; 18: 1342
• 25e Song W, Lu W, Wang J, Lu P, Wang Y. J. Org. Chem. 2010; 75: 3481
• 25f Moreira NM, Martelli LS. R, de Julio KI. R, Zukerman-Schpector J, Opatz T, Corrêa AG. Eur. J. Org. Chem. 2020; 4563
• 26a Dai C, Xie Z, Li M, Wang C. Asian J. Org. Chem. 2020; 9: 61
• 26b Liu H, Zhou Z, Sun Q, Li Y, Li Y, Liu J, Yan P, Wang D, Wang C. ACS Comb. Sci. 2012; 14: 366
• 26c Zhou Z, Liu H, Sun Q, Li Y, Yang J, Liu J, Yan P, Wang C. Synlett 2012; 23: 2255
• 26d Li Y, Xue Z, Ye W, Liu J, Yao J, Wang C. ACS Comb. Sci. 2014; 16: 113
• 26e Zhang J, Yao J, Liu J, Xue S, Li Y, Wang C. RSC Adv. 2015; 5: 48580
• 26f Ye W, Li Y, Zhou L, Liu J, Wang C. Green Chem. 2015; 17: 188
• 26g Xue S, Yao J, Liu J, Wang L, Liu X, Wang C. RSC Adv. 2016; 6: 1700
• 26h Qing X, Wang T, Zhang F, Wang C. RSC Adv. 2016; 6: 95957
• 26i Xue S, Li Y, Wang L, Liu J, Qing X, Wang C. Synlett 2016; 27: 1083
• 26j Wang T, Qing X, Dai C, Su Z, Wang C. Org. Biomol. Chem. 2018; 16: 2456
• 27 Luo N, Wang S, Zhang Y, Xin J, Wang C. J. Org. Chem. 2020; 85: 14219
• 28 CCDC 2079819 (3v) contains the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/getstructures.