Regioselective Synthesis of 2,4- and 2,5-Disubstituted 1,3-Thiazoles from 2-Oxo-2-(amino)ethanedithioates via Base-Catalyzed Cyclization

Abstract

Facile and efficient methods are reported for the synthesis of 2,4- and 2,5-disubstituted-1,3-thiazoles by the cyclization of 2-oxo-2-(amino)ethanedithioates with TosMIC and α-haloketones in high yields. Key structures were confirmed based on X-ray crystallographic studies. In addition, investigation of ground state geometry, electronic and molecular structural properties, FMOs, global reactivity descriptors, MEP and NCI analyses were predicted to access the information related to the stability, reactivity, and strength of the interactions present in the molecules by quantum chemical calculations. Further, the potency of derivatives was tested against the SARS-Cov2 receptor (PDB ID: 7mc6) via molecular docking approach with binding scores of –6.0 to –8.4 kcal/mol.

Key words

thiazole - TosMIC - α-haloketones - X-ray crystallographic studies - DFT Studies - molecular docking

Publication History

Received: 05 September 2023

Accepted after revision: 14 November 2023

Accepted Manuscript online:
14 November 2023

Article published online:
18 December 2023

• References

• 1 Maganti LH. B, Ramesh D, Vijayakumar BG, Khan MI. K, Dhayalan A, Kamalraja J, Kannan T. RSC Adv. 2022; 12: 8771
• 2 Borcea AM, Ionuț I, Crișan O, Oniga O. Molecules 2021; 26: 624
• 3 Petrou A, Fesatidou M, Geronikaki A. Molecules 2021; 26: 3166
• 4 Mishra R, Sharma PK, Verma PK, Tomer I, Mathur G, Dhakad PK. J. Heterocycl. Chem. 2017; 54: 2103
• 5 Hupfer ML, Kaufmann M, Roussille L, Preiß J, Weiß D, Hinrichs K, Deckert V, Dietzek B, Beckert R, Presselt M. Langmuir 2019; 35: 2561
• 6 Radhakrishnan R, Sreejalekshmi KG. J. Org. Chem. 2018; 83: 3453
• 7 Seed AJ, Sampson P. Liq. Cryst. 2017; 44: 1894
• 8 Arshadi S, Vessally E, Edjlali L, Hosseinzadeh-Khanmiri R, Ghorbani-Kalhor E. Beilstein J. Org. Chem. 2017; 13: 625
• 9 Sasmal PK, Chandrasekhar A, Sridhar S, Iqbal J. Tetrahedron 2008; 64: 11074
• 10 Ansari MA, Yadav D, Singh MS. J. Org. Chem. 2020; 85: 8320
• 11 Liu XW, Shi JL, Yan JX, Wei JB, Peng K, Dai L, Li CG, Wang BQ, Shi ZJ. Org. Lett. 2013; 15: 5774
• 12 Liu D, Ding Q, Fu Y, Song Z, Peng Y. Org. Lett. 2019; 21: 2523
• 13 Miura T, Funakoshi Y, Fujimoto Y, Nakahashi J, Murakami M. Org. Lett. 2015; 17: 2454
• 14 Wu Y.-J. Prog. Heterocycl. Chem. 2021; 33: 277
• 15 Tani S, Uehara TN, Yamaguchi J, Itami K. Chem. Sci. 2014; 5: 123
• 16 Hantzsch A, Weber JH. Ber. Dtsch. Chem. Ges. 1887; 20: 3118
• 17 Sheldrake PW, Matteucci M, McDonald E. Synlett 2006; 460
• 18 Tang X, Yang J, Zhu Z, Zheng M, Wu W, Jiang H. J. Org. Chem. 2016; 81: 11461
• 19 Castagnolo D, Pagano M, Bernardini M, Botta M. Synlett 2009; 2093
• 20 Sanz-Cervera JF, Blasco R, Piera J, Cynamon M, Ibanez I, Murguia M, Fustero S. J. Org. Chem. 2009; 74: 8988
• 21 Ishiwata Y, Togo H. Synlett 2008; 2637
• 22 Meng X.-Y, Zhang H.-X, Mezei M, Cui M. Curr. Comput. Aided Drug Des. 2011; 7: 146
• 23 Ravi Singh K, Lohith TN, Ananth Nag T, Sridhar MA, Sadashiva MP. Mol. Cryst. Liq. Cryst. 2023; 763: 54
• 24 van Mourik T, Bühl M, Gaigeot M.-P. Philos. Trans. Ser. A, Math. Phys. Eng. Sci. 2014; 372: 20120488
• 25 Ravi Singh K, Santhosh C, Swaroop TR, Sadashiva MP. Org. Biomol. Chem. 2022; 20: 5771
• 26 Kiran KR, Swaroop TR, Rajeev N, Anil SM, Rangappa KS, Sadashiva MP. Synthesis 2020; 52: 1444
• 27 Rajeev N, Swaroop TR, Anil SM, Bommegowda YK, Rangappa KS, Sadashiva MP. Synlett 2017; 28: 2281
• 28 Lingaraju GS, Swaroop TR, Vinayaka AC, Sharath Kumar KS, Sadashiva MP, Rangappa KS. Synthesis 2012; 44: 1373
• 29 Tumakuru Nagarajappa L, Ravi Singh K, Kabuyaya Isamura B, Vinay Kumar KS, Mandayam Anandalwar S, Sadashiva MP. J. Biomol. Struct. Dyn. 2023; 41: 11122
• 30 Vinay Kumar KS, Lingaraju GS, Bommegowda YK, Vinayaka AC, Bhat P, Pradeepa Kumara CS, Rangappa KS, Gowda DC, Sadashiva MP. RSC Adv. 2015; 5: 90408
• 31 Santhosh C, Singh KR, Sheela K, Swaroop TR, Sadashiva MP. J. Org. Chem. 2023; 88: 11486
• 32 Preetham R, Vijaya Kumar MS, Swaroop TR, Divyashree S, Kiran KR, Sreenivasa MY, Sadashiva MP, Rangappa KS. ChemistrySelect 2022; 7: e202203079
• 33 Chaitra K, Ravi Singh K, Raghu MS, Sadashiva MP, Prashanth KN. Chem. Data Collect. 2022; 41: 100928
• 34 Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Petersson GA, Nakatsuji H, Li X, Caricato M, Marenich A, Bloino J, Janesko BG, Gomperts R, Mennucci B, Hratchian HP, Ortiz JV, Izmaylov AF, Sonnenberg JL, Williams-Young D, Ding F, Lipparini F, Egidi F, Goings J, Peng B, Petrone A, Henderson T, Ranasinghe D, Zakrzewski VG, Gao J, Rega N, Zheng G, Liang W, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Throssell K, Montgomery JA. Jr, Peralta JE, Ogliaro F, Bearpark M, Heyd JJ, Brothers E, Kudin KN, Staroverov VN, Keith T, Kobayashi R, Normand J, Raghavachari K, Rendell A, Burant JC, Iyengar SS, Tomasi J, Cossi M, Millam JM, Klene M, Adamo C, Cammi R, Ochterski JW, Martin RL, Morokuma K, Farkas O, Foresman JB, Fox DJ. Gaussian 09, Revision D.01 . Gaussian Inc; Wallingford CT: 2016
• 35 Hanwell MD, Curtis DE, Lonie DC, Vandermeerschd T, Zurek E, Hutchison GR. J. Cheminform 2012; 4: 17
• 36 Manjunatha B, Bodke Y, Jain S, Lohith TN. J. Mol. Struct. 2021; 1244: 130933
• 37 Lohith TN, Shamanth S, Sridhar MA, Mantelingu K, Lokanath NK. J. Mol. Struct. 2022; 1252: 132203
• 38 Lu T, Chen F. J. Comput. Chem. 2012; 33: 580
• 39 Humphrey W, Dalke A, Schulten K. J. Mol. Graph. 1996; 14: 27
• 40 CCDC 2213027 (3a) and 2224453 (5a) contain 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/structures