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Research Articles

Computational and experimental analysis of catalyst-free and expeditious synthesis of Benzo[4,5]imidazo[2,1-b]thiazole derivatives

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Pages 1-11 | Received 07 Jun 2023, Accepted 27 Sep 2023, Published online: 06 Oct 2023

References

  • (a) Xie L-Y, Qu J, Peng S, et al. Selectfluor-mediated regioselective nucleophilic functionalization of N-heterocycles under metal- and base-free conditions. Green Chem. 2018;20:760–764. (b) Guo XX, Gu DW, Wu ZX, et al. Copper-catalyzed C–H functionalization reactions: efficient synthesis of heterocycles. Chem Rev. 2015;115:1622–1651; (c) Kerru N, Gummidi L, Maddila S, et al. A review on recent advances in nitrogen-containing molecules and their biological applications. Molecules. 2020;25:1909.
  • (a) Romagnoli R, Baraldi PG, Prencipe F, et al. Design, synthesis and antiproliferative activity of novel heterobivalent hybrids based on imidazo[2,1-b][1,3,4]thiadiazole and imidazo[2,1-b][1,3]thiazole scaffolds. Eur J Med Chem. 2015;101:205–217. (b) Ali AR, El-Bendary ER, Ghaly MA, et al. Synthesis, in vitro anticancer evaluation and in silico studies of novel imidazo[2,1-b]thiazole derivatives bearing pyrazole moieties. Eur J Med Chem. 2014;75:492–500; (c) Shareef Mohd A, Khan I, Babu BN, et al. A comprehensive review on the therapeutic versatility of imidazo [2,1-b]thiazoles. Curr Med Chem. 2020;27:6864–6887; (d) Kishore KG, Islas-Jácome A, Rentería-Gómez A, et al. Synthesis of unsymmetrical bis-heterocycles containing the imidazo[2,1-b]thiazole framework and their benzo[d]fused analogues by an acid-free Groebke–Blackburn–Bienaymé reaction. Tetrahedron Lett. 2016;57:3556–3560.
  • Mavrova AT, Anichina KK, Vuchev DI, et al. Synthesis, structure and antihelmintic activity of some novel derivatives of thiazolo[3,2-a]benzimidazole-3(2H)-one. J Univ Chem Tech Metall. 2003;38:251–256.
  • Bakbardina OV, Nurmagambetova RT, Gazalieva MA, et al. Synthesis and fungicidal activity of pseudo-thiohydantoins, their 5-arylidene derivatives, and 5-arylidene-3-β-aminothiazolid-2,4-one hydrochlorides. Pharm Chem J. 2006;40:537–539. doi:10.1007/s11094-006-0187-3
  • Mavrova AT, Yancheva D, Anastassova N, et al. Synthesis, electronic properties, antioxidant and antibacterial activity of some new benzimidazoles. Bioorg Med Chem. 2015;23:6317–6326. doi:10.1016/j.bmc.2015.08.029
  • Chaturvedi RN, Pendem K, Patel VP, et al. Design, synthesis, molecular docking, and in vitro antidiabetic activity of novel PPARγ agonist. Monatsh Chem. 2018;149:2069–2084. doi:10.1007/s00706-018-2207-x
  • Whittaker M, Davidson AH, Spavold ZM, et al. Preparation of γ-butyrolactol ethers as platelet activating factor antagonists. PCT Int. Appl. WO 9,117,157, 1991. Chem Abstr. 1992;117:26321q.
  • Ao E, Tanaka H, Nakao T, et al. Nicotinamide derivatives. Jpn. Kokai Tokkyo Koho JP 0,377,881, 1991. Chem Abstr. 1991;115:255995p.
  • Darwish SA, El-Kerdawy Mohamed M, Elsheakh AR, et al. New tilomisole-based benzimidazothiazole derivatives as anti-inflammatory agents: synthesis, in vivo, in vitro evaluation, and in silico studies. Bioorg Chem. 2022;120:105644. doi:10.1016/j.bioorg.2022.105644
  • Dijoseph JF, Palumbo GJ, Crossley R, et al. Gastric antisecretory activity of an acid stable H+/K+ ATPase inhibitor, WY-26,769. Drug Dev Res. 1991;23:57–64. doi:10.1002/ddr.430230106
  • Kohara A, Toya T, Tamura S, et al. Radioligand binding properties and pharmacological characterization of 6-amino-N-cyclohexyl-N,3-dimethylthiazolo[3,2-a]benzimidazole-2-carboxamide (YM-298198), a high-affinity, selective, and noncompetitive antagonist of metabotropic glutamate receptor type 1. J Pharm Exp Ther. 2005;315:163–169. doi:10.1124/jpet.105.087171
  • Wang J, Zhang W, Zhao Z, et al. Construction of benzo[d]imidazo[2,1-b]thiazole derivatives via a simple multi-component domino cyclization. Res Chem Intermed. 2018;44:613–628. doi:10.1007/s11164-017-3123-0
  • (a) Shen G, Yang B, Huang X, et al. Copper- and palladium-catalyzed cross-coupling reactions for the synthesis of N-fused benzo[4,5]imidazo[2,1-b]thiazole derivatives via substituted trans-1,2-diiodoalkenes, 1H-benzo[d]imidazole-2-thiols, and halobenzenes. J Org Chem. 2017;82:3798–3805. (b) Xu H, Zhang Y, Huang J, et al. Copper-catalyzed synthesis of N-fused heterocycles through regioselective 1,2-aminothiolation of 1,1-Dibromoalkenes. Org Lett. 2010;12:3704–37007.
  • (a) Kuang J, Xia Y, Yang A, et al. Copper-catalyzed aminothiolation of terminal alkynes with tunable regioselectivity. Chem Commun. 2019;55:1813–1816. (b) Xiao D, Han L, Sun Q, et al. Copper-mediated synthesis of N-fused heterocycles via Csp–S coupling reaction and 5-endo-dig cyclization sequence. RSC Adv. 2012;2:5054–5057.
  • Jana S, Chakraborty A, Shirinian VZ, et al. Synthesis of benzo[4,5]imidazo[2,1-b]thiazole by copper(II)-catalyzed thioamination of nitroalkene with 1H-Benzo[d]imidazole-2-thiol. Adv Synth Catal. 2018;360:2402–2408. doi:10.1002/adsc.201800393
  • Mavrova AT, Anichina KK, Vuchev DI, et al. Synthesis and antitrichinellosis activity of some 2-substituted-[1,3]thiazolo[3,2-a]benzimidazol-3(2H)-ones. Bioorg Med Chem. 2005;13:5550–5559. doi:10.1016/j.bmc.2005.06.046
  • Ochiai M, Tada N, et al. Domino Michael addition-carbene rearrangement-cyclization reaction of 1-alkynyl(aryl)-λ3-bromanes with 2-mercapto-1,3-benzazoles. Chem Commun. 2005;40:5083–5085. doi:10.1039/b509269h
  • Ambethkar S, Vellimalai M, Padmini V, et al. Iodine-mediated C–N and C–S bond formation: regioselective synthesis of benzo[4,5]imidazo[2,1-b]thiazoles. New J Chem. 2017;41:75–80. doi:10.1039/C6NJ02102F
  • Neochoritis CG, Zarganes-Tzitzikas T, Stephanidou-Stephanatou J, et al. Dimethyl acetylenedicarboxylate: a versatile tool in organic synthesis. Synthesis (Mass). 2014;46:537–585. doi:10.1055/s-0033-1340615
  • Wade JJ, et al. Reaction of 2H-benzimidazole-2-thione with dimethyl acetylenedicarboxylate. J Org Chem. 1979;44:1816–1819. doi:10.1021/jo01325a014
  • (a) Dandia A, Singh R, Joshi J, et al. 2,2,2-Trifluoroethanol as green solvent in organic synthesis: a review. Mini Rev Org Chem. 2014;11:462–476. (b) Alinezhad H, Tajbakhsh M, Zare M, et al. Catalyst-free one-pot synthesis of 1,4,5-trisubstituted pyrazoles in 2,2,2-trifluoroethanol. J Fluor Chem. 2011;132;995–1000; (c) Liu J, Wang L, Wang X, et al. Fluorinated alcohol-mediated [4 + 3] cycloaddition reaction of indolyl alcohols with cyclopentadiene. Org Biomol Chem. 2016;14:11510–11517.
  • (a) Singh R, Singh A, Bhardwaj D, et al. Selective and solvent-free synthesis of isoxazole-containing spiro-thiazolidinones using TiO2-SO3H as solid catalyst. ChemistrySelect. 2019;4:9600–9607; (b) Singh R, Saini MR, Bhardwaj D, Singh A, et al. An expedient synthesis of new imino-thiazolidinone grafted dispiro-pyrrolidine-oxindole/indeno hybrids via a multicomponent [3+2] cycloaddition reaction in a deep eutectic solvent. New J Chem. 2020;44:7923–7931; (c) Bhardwaj D, Singh R, et al. A strategic approach for synthesis of benzimidazo[2,1-b]thiazolidinone appended dispirooxindole hybrids via [3 + 2] cycloaddition using fluoro-ethanol as solvent. Tetrahedron Lett. 2021;85:153491.
  • Kumavat PP, Jangale AD, Patil DR, et al. Green synthesis of symmetrical N, N′-disubstituted thiourea derivatives in water using solar energy. Environ Chem Lett. 2013;11:177–182. doi:10.1007/s10311-012-0394-y
  • Ponra S, Majumdar KC, et al. Brønsted acid-promoted synthesis of common heterocycles and related bio-active and functional molecules. RSC Adv. 2016;6:37784–37922. doi:10.1039/C5RA27069C
  • Sharma S, Mohammad I. The computational study, thermodynamic parameters, and partial inhibition of spermatogenesis exhibited by toxicophores scaffolds of an organic–inorganic hybrid complex of tributyltin (IV). Appl Organomet Chem. 2022;36:e6776. doi:10.1002/aoc.6776
  • Verma D, Sharma S, Vashishtha M, et al. Evaluation of optimized molecular structure-antimicrobial and antioxidant efficacy relationship of schiff bases. Environ Sci Poll Res. 2023;30:20874–20886.
  • Sharma S, Kumar R, Kumar P, et al. New insights into the predicament of DFT assisted optimized energy, stability and distortions of optimized topologies of some novel complexes of Zirconium (IV) and enhancement of antimicrobial potential. Appl Organomet Chem. 2019;33:e5080. doi:10.1002/aoc.5080
  • Rathore A, Sharma S, Sharma A, et al. Evaluation of structure-reactivity correlation of efficient corrosion inhibitor ionic liquids for mild steel in acidic medium. J Dispersion Sci Technol 2023;44(4).
  • Fisicaro E, Compari C, Braibanti A, et al. Hydrophobic hydration processes: intensity entropy and null thermal free energy and density entropy and motive free energy. ACS Omega. 2019;4:19526–19547. doi:10.1021/acsomega.9b01440

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