CC BY 4.0 · SynOpen 2023; 07(03): 414-421
DOI: 10.1055/a-2149-4113
paper

Pyrrolidinium Acetate (PyrrIL) as a Green and Recyclable Catalyst: Synthesis of 2-Phenyl Benzimidazoles and 2-Phenyl Benzothiazoles under Solvent-Free Conditions at Room Temperature

Ramesh Katla
a   Foreign Visiting Professor, Organic Chemistry Laboratory-IV, School of Chemistry and Food, Federal University of Rio Grande-FURG, Rio Grande, RS-Brazil, Brazil
b   Research Scientist, Department of Hematology/Oncology, University of Virginia, Charlottesville, VA, USA
,
Rakhi Katla
c   Organic Catalysis and Biocatalysis Laboratory - LACOB, Federal University of Grande Dourados-UFGD, Dourados/MS, Brazil
› Institutsangaben
R.K. thanks the ‘CNPq-TWAS fellow’, R.K. (Foreign Visiting Professor-Edital N.03/2020 PROPESP/FURG) thanks to the Pró-Reitoria de Pesquisa e Pós-Graduação, Universidade Federal do Rio Grande (PROPESP-FURG),, Rio Grande-RS for visiting professorship.


Abstract

Benzimidazoles and benzothiazoles are a class of pharmacologically potential compounds, which exhibited antimicrobial, anticancer, and anti-inflammatory activities. These can be obtained by simple condensation of o-phenylenediamine or o-aminothiophenol with aromatic aldehydes. The synthetic protocol can be accomplished/improved by varying reaction parameters such as temperature, solvents, and catalysts. To develop such condensation reactions in a sustainable way, nontoxic solvents and eco- friendly catalysts are presently used. In this study, we proposed a novel and interesting strategy for obtaining diversely substituted 2-phenyl benzimidazole and 2-phenyl benzothiazole derivatives via a one-pot protocol, employing pyrrolidinium ionic liquid as a green and environmentally benign catalyst under solvent-free conditions at room temperature in an open atmosphere. The resulting products were obtained in good to excellent yields within a short reaction time (3–20 min). A plausible mechanism was also discussed.

Supporting Information



Publikationsverlauf

Eingereicht: 23. Juni 2023

Angenommen nach Revision: 04. August 2023

Accepted Manuscript online:
07. August 2023

Artikel online veröffentlicht:
08. September 2023

© 2023. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by/4.0/)

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  • References and Notes

  • 1 Keskin S, Kayrak-Talay D, Akman U, Hortaçsu O. J. Supercrit. Fluids 2007; 43: 150
  • 2 Sobrinho RC. M. A, Oliveira PM, D’Oca CR. M, Russowsky D, D’Oca MG. M. RSC Adv. 2017; 7: 3214
  • 3 Forbes DC, Law AM, Morrison DW. Tetrahedron Lett. 2006; 47: 1699
  • 4 Khan FA, Dash J, Satapathy R, Upadhyay SK. Tetrahedron Lett. 2004; 45: 3055
  • 5 Morrison DW, Forbes DC, Davis JH. Jr. Tetrahedron Lett. 2001; 42: 6053
  • 6 Anouti M, Caillon-Caravanier M, Dridi Y, Galiano H, Lemordant D. J. Phys. Chem. B 2008; 112: 13335
  • 7 Wilkes JS. Green Chem. 2002; 4: 73
  • 8 Welton T. Chem. Rev. 1999; 99: 2071
  • 9 Dupont J, de Souza RF, Suarez PA. Chem. Rev. 2002; 102: 3667
  • 10 Earle MJ, Seddon KR. Pure Appl. Chem. 2000; 72: 1391
  • 11 Majumdar S, Chakraborty A, Bhattacharjee S, Debnath S, Maiti DK. Tetrahedron Lett. 2016; 57. 4595
  • 12 Wan JJ, Gan SF, Wu JM, Pan Y. Green Chem. 2009; 11: 1633
  • 13 Lyu L, Cai L, Wang Y, Huang J, Zeng X, Liu P. RSC Adv. 2017; 78: 49374
  • 14 Katla R, Katla R, Domingues NL. C. ChemistrySelect 2022; 7: e202200582
  • 15 Katla R, Chowrasia R, Manjari PS, Domingues NL. C. RSC Adv. 2015; 5: 41716
  • 16 Gunawardana GP, Koehn FE, Lee AY, Clardy J, He HY, Faulkner DJ. J. Org. Chem. 1992; 57: 1523
  • 17 Carroll AR, Scheuer PJ. J. Org. Chem. 1990; 55: 4426
  • 18 Si W, Zhang T, Li Y, She D, Pan W, Gao Z, Ning J, Mei X. J. Pest. Sci. 2017; 14: 40
  • 19 Rajasekhar S, Maiti B, Balamurali MM, Balamurali K, Shikha A. Curr. Org. Chem. 2019; 16: 1078
  • 20 Chugunova E, Boga C, Sazykin I, Cino S, Micheletti G, Mazzanti A, Sazykina M, Burilov A, Khmelevtsova L, Kostina N. Eur. J. Med. Chem. 2015; 93: 349
  • 21 Kashyap SJ, Garg VK, Sharma PK, Kumar N, Dudhe R, Gupta JK. Med. Chem. Res. 2012; 21: 2123
  • 22 Haroun M, Tratrat C, Kositsi K, Tsolaki E, Petrou A, Aldhubiab B, Attimarad M, Harsha S, Geronikaki A, Venugopala KN, Elsewedy HS, Sokovic M, Glamoclija J, Ciric A. Curr. Top. Med. Chem. 2018; 18: 75
  • 23 Racané L, Zlatar I, Perin N, Cindric M, Radovanovic V, Banjanac M, Shanmugam S, Stojkovic MR, Brajsa K, Hranjec M. Molecules 2021; 26: 4935
  • 24 Elgawish MS, Nafie MS, Yassen AS. A, Yamada K, Ghareb N. New J. Chem. 2022; 46: 4239
  • 25 Irfan A, Batool F, Naqvi SA. Z, Islam A, Osman SM, Nocentini A, Alissa SA, Supuran CT. J. Enzyme Inhib. Med. Chem. 2020; 35: 265
  • 26 Porcari AR, Devivar RV, Kucera LS, Drach JC, Townsend LB. J. Med. Chem. 1998; 41: 1252
  • 27 Stefańska JZ, Gralewska R, Starościak BJ, Kazimierczuk Z. Pharmazie 1999; 54: 879
  • 28 Migawa MT, Girardet J.-L, Walker JA, Koszalka GW, Chamberlain SD, Drach JC, Townsend LB. J. Med. Chem. 1998; 41: 1242
  • 29 Mori A, Sekiguchi A, Masui K, Shimada T, Horie M, Osakada K, Kawamoto M, Ikeda T. J. Am. Chem. Soc. 2003; 125: 1700
  • 30 Mylari BL, Larson ER, Beyer TA, Zembrowski WJ, Aldinger CE, Dee MF, Siegel TW, Singleton DH. J. Med. Chem. 1991; 34: 108
  • 31 Aiello S, Wells G, Stone EL, Kadri H, Bazzi R, Bell DR, Stevens MF. G, Matthews CS, Bradshaw TD, Westwell AD. J. Med. Chem. 2008; 51: 5135
  • 32 Geng J, Li M, Wu L, Ren J, Qu X. J. Med. Chem. 2012; 55: 9146
  • 33 Singh N, Jang DO. Org. Lett. 2007; 9: 1991
  • 34 Chen TR. J. Mol. Struct. 2005; 737: 35
  • 35 Yang D, Fokas D, Li J, Yu L, Baldino CM. A. Synthesis 2005; 47
  • 36 Niknam K, Fatehi-Raviz A. J. Iran. Chem. Soc. 2007; 4: 438
  • 37 Su Y.-S, Sun C.-M. Synlett 2005; 1243
  • 38 Olguin LF, Jiménez-Estrada M, Barzana E, Navarro-Ocaña A. Synlett 2005; 340
  • 39 Heravi MM, Tajbakhsh M, Ahmadi AN, Mohajerani B. Monatsh. Chem. 2006; 137: 175
  • 40 Hein D, Alheim RJ, Leavitt J. J. Am. Chem. Soc. 1957; 79: 427
  • 41 Sharghi H, Asemani O, Khalifeh R. Synth. Commun. 2008; 38: 1128
  • 42 Itoh T, Nagata K, Ishikawa H, Ohsawa A. Heterocycles 2004; 63: 2769
  • 43 Rudrawar S, Kondaskar A, Chakraborti AK. Synthesis 2005; 2521
  • 44 Ramesh K, Murthy SN, Nageswar YV. D. Tetrahedron Lett. 2011; 52: 2362
  • 45 Ramesh K, Murthy SN, Karnakar K, Nageswar YV. D. Tetrahedron Lett. 2011; 52: 3937
  • 46 Ramesh K, Murthy SN, Karnakar K, Nageswar YV. D. Tetrahedron Lett. 2011; 52: 4734
  • 47 Ramesh K, Murthy SN, Karnakar K, Nageswar YV. D, Vijayalakhshmi K, Prabhavathi Devi BL. A, Prasad RB. N. Tetrahedron Lett. 2012; 53: 1126
  • 48 Ramesh K, Madhav B, Murthy SN, Nageswar YV. D. Synth. Commun. 2012; 42: 258
  • 49 Ramesh K, Murthy SN, Nageswar YV. D. Synth. Commun. 2012; 42: 2471
  • 50 Katla R, Katla R, Goulart TB, Rosa DS, Rosa GR. Synlett 2022; 33: 1637
  • 51 Katla R, Chowrasia R, Manjari PS, Silva CD. G, Santos BF, Domingues NL. C. New J. Chem. 2016; 40: 9471
  • 52 Katla R, Katla R, Silva CD. G, Santos BF, Branquinho TA, Ferro CT. B, Domingues NL. C. ChemistrySelect 2019; 4: 13304
  • 53 Katla R, Chowrasia R, Silva CD. G, de Oliveira AR, Santos BF, Domingues NL. C. Synthesis 2017; 49: 5143
  • 54 Katla R, Katla R. New J. Chem. 2022; 46: 13918
  • 55 Katla R, Katla R, Domingues NL. C. Synthesis 2022; 54: 4608
  • 56 Katla R, Katla R, Oreste EQ, Kessler F. Synthesis 2023; 55: 799
  • 57 Shaterian HR, Mohammadnia M. J. Mol. Liq. 2013; 177: 162
  • 58 Anastas P, Eghbali N. Chem. Soc. Rev. 2010; 39: 301
  • 59 Danten Y, Cabaço MI, Coutinho JA. P, Pinaud N, Besnard M. J. Phys. Chem. B 2016; 120: 5243
  • 60 Shaterian HR, Aghakhanizadeh M. Chin. J. Catal. 2013; 34: 1690
  • 61 Singh SK, Savoy AW. J. Mol. Liq. 2020; 297: 112038
  • 62 Bardajee GR, Mohammadi M, Yari H, Ghaedi A. Chin. Chem. Lett. 2016; 27: 265
  • 63 Riadi Y, Mamouni R, Azzalou R, Haddad ME, Routier S, Guillaumet G, Lazar S. Tetrahedron Lett. 2011; 52: 3492
  • 64 Padalkar VS, Gupta VD, Phatangare KR, Patil VS, Umape N, Sekar PG. Green Chem. Lett. Rev. 2012; 5: 139
  • 65 Teimouri A, Chermahini AN, Salavati H, Ghorbanian L. J. Mol. Catal. A: Chem. 2013; 373: 38
  • 66 Inamdar SM, More VK, Mandal SK. Tetrahedron Lett. 2013; 54: 579
  • 67 Shelkar R, Sarode S, Nagarkar J. Tetrahedron Lett. 2013; 54: 6986
  • 68 Chen GF, Jia HM, Zhang LY, Chen B.-H, Li JT. Ultrason. Sonochem. 2013; 20: 627