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Synthesis and Characterization of Thiazole Compounds in the Presence of Various Reagents, Catalysts and Solvents

Year 2022, Volume: 26 Issue: 4, 757 - 767, 31.08.2022
https://doi.org/10.16984/saufenbilder.950016

Abstract

The reaction medium plays a key role in organic synthesis and pharmaceutical research. There are many opinions on choosing the best condition, including cost and environmental implications, but the main requirement is that they have the necessary interaction with solvents to cause dissolution, precipitation, stabilization, or instability. For this purpose, in this article synthesis of the thiazole ring was made under various reaction conditions. So new compounds 2-(isoquinolin-5-ylimino)-3-phenylthiazolidin-4-one (1), (4-amino-3-phenylthiazol-2(3H)-ylidene) isoquinolin-5-amine (2), (4-amino-3-phenylthiazol-2(3H)-ylidene) isoquinolin-5-amine (3) were synthesized from the reaction between thiourea derivative and monochloroacetic acid, diethyloxalate and chloro acetonitrile. For this synthesizes were created in various reaction conditions, using different bases (sodium acetate/sodyum etoksit/ triethylamine or pyridine) and solvents (1,4-dioxane, toluene, acetic acid, ethanol, tetrahydrofuran, dimethyl formamide). At the end of these reactions, the best efficiency was obtained with the one-pot reaction using THF/DMF, Et3N. The structures of all novel compounds reported herein were established using FT-IR, 1H NMR, and 13C NMR spectra as well as elemental analysis technique.

Supporting Institution

Çanakkale Onsekiz Mart Üniversitesi

Project Number

FHD-2020-3440

Thanks

The author would like to thank the Çanakkale Onsekiz Mart University Scientific Research Projects Commission (BAP) for contributing to the financial portion of the project.

References

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  • [20] S. D’Alessandro, D. Scaccabarozzi, L. Signorini, F. Perego, D. P. Ilboudo, P., Ferrante, S. Delbue, “The use of antimalarial drugs against viral infection,” Microorganisms, vol. 8, no. 1, pp. 85, 2020.
  • [21] H. N. Karade, B. N. Acharya, M. Sathe, M. P. Kaushik, “Design, synthesis, and antimalarial evaluation of thiazole-derived amino acids,” Medicinal Chemistry Research, vol. 17, no. 1, pp. 19–29, 2008.
  • [22] P. Ghosh, M. J. Deka, A. K. Saikia, “Lewis acid mediated intramolecular C–O bond formation of alkanol-epoxide leading to substituted morpholine and 1, 4-oxazepane derivatives: total synthesis of (±) –viloxazinec,” Tetrahedron, vol. 72, no. 5, pp. 690-698, 2016.
  • [23] R. M. Abdel-Rahman “Role of uncondensed 1,2,4-triazine compounds and related heterobicyclic systems as therapeutic agents: a review,” Pharmazie, vol. 56, no. 1, pp. 18-22, 2001.
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  • [26] N. Berber, M. Arslan, F. Vural, A. Ergun, N. Gençer, O. Arslan, “Synthesis of new series of thiazol‐(2(3H)‐ylideneamino) benzene- sulfonamide derivatives as carbonic anhydrase inhibitors,” Journal of Biochemical and Molecular Toxicology, vol. 34, no. 12, pp. e22596, 2020.
  • [27] N. Berber, M. Arslan, Ç. Bilen, Z. Sackes, N. Gencer, O. Arslan, “Synthesis and evaluation of new phthalazine substituted β-lactam derivatives as carbonic anhydrase inhibitors,” Russian Journal of Bioorganic Chemistry, vol. 41, no. 4 pp. 414-20, 2015.
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  • [30] H. Saad “The synthesis of some new sulfur-bearing various heterocyclic systems derived from asymmetrical n,n′-disubstituted thiourea derivatives,” Phosphorus, Sulfur, and Silicon, vol. 181, no. 7, pp. 1557-1567, 2006.
  • [31] H. A. Abdel-Azız, H. S. El-Zahabi, K. M. Dawood, “Microwave-assisted synthesis and in-vitro anti-tumor activity of 1,3,4-triaryl-5-N-arylpyrazole carboxamides,” European Journal of Medicinal Chemistry, vol. 45, no. 6, pp. 2427-2432, 2010.
  • [32] H. M. Abumelha “Synthesis and antioxidant assay of new nicotinonitrile analogues clubbed thiazole, pyrazole and/or pyridine ring systems,” Journal of Heterocyclic Chemistry, vol. 57, no. 3, pp. 1011-1022, 2020.
  • [33] Y. Feng, X. Ding, T. Chen, L. Chen, F. Liu, X. Jia, X. Luo, X. Shen, K. Chen, H. Jiang, H. Wang, H. Liu, D. Liu, “Design, synthesis, and interaction study of quinazoline-2 (1 H)-thione derivatives as novel potential Bcl-xL inhibitors,” Journal of Medicinal Chemistry, vol. 53, no. 9, pp. 3465-3479, 2010.
  • [34] H. A. Morsy, A. H. Moustafa “A facile approach for synthesis of thiazines-, thiazoles-and triazoles-annulated 6-styryl-2-thiouracil derivative,” Journal of the Iranian Chemical Society, vol. 17, no. 1, pp. 119-125, 2020.
  • [35] M. Sathishkumar, S. Nagarajan, P. Shanmugavelan, M. Dinesh, A. Ponnuswamy, “A facile, rapid, one-pot regio/stereoselective synthesis of 2-iminothiazolidin-4-ones under solvent/ scavenger-free conditions,” Beilstein Journal of Organic Chemistry, vol. 9, no. 1, pp. 689-697, 2013.
  • [36] A. R. Sayed, S. M. Gomha, E. A. Taher, Z. A. Muhammad, H. R. El-Seedi, H. M. Gaber, M. M. Ahmed, “One-pot synthesis of novel thiazoles as potential anti-cancer agents,” Drug Design, Development and Therapy, vol. 14, no. 2020, pp. 1363, 2020.
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Year 2022, Volume: 26 Issue: 4, 757 - 767, 31.08.2022
https://doi.org/10.16984/saufenbilder.950016

Abstract

Project Number

FHD-2020-3440

References

  • [1] T. Akiyama, J. Iwai, “Scandium trifluoro- methanesulfonate-catalyzed chemoselective allylation reactions of carbonyl compounds with tetraallylgermane in aqueous media,” Tetrahedron, vol. 55, no. 24, pp. 7499-7508, 1999.
  • [2] M. S. Saini, A. Kumar, J. Dwivedi, R. Singh, “A review: biological significances of heterocyclic compounds,” International Journal of Pharma Sciences and Research, vol. 4, no. 3, pp. 66-77, 2013.
  • [3] Y. Cheng, Z. T. Huang, M. X. Wang, “Heterocyclic enamines: The versatile intermediates in the synthesis of heterocyclic compounds and natural products,” Current Organic Chemistry, vol. 8, no. 4, pp. 325-51, 2004.
  • [4] N. Kaur “Review on the synthesis of six-membered N, N-heterocycles by microwave irradiation,” Synthetic Communications, vol. 45, no. 10, pp. 1145-82, 2015.
  • [5] N. Kaur “Photochemical reactions: synthesis of six-membered N-heterocycles,” Current Organic Synthesis, vol. 14, no. 7, pp. 972-98, 2017.
  • [6] M. Haji “Multicomponent reactions: A simple and efficient route to heterocyclic phosphonates,” Beilstein Journal of Organic Chemistry, vol. 12, no. 1, pp. 1269-1301, 2016.
  • [7] S. Sarkar, A. A. Siddiqui, S. J. Saha, De. Rudranil, S. Mazumder, C. Banerjee, M. S. Iqbal, S. Nag, S. Adhikari, U. Bandyopadhyay, “Antimalarial Activity of small-molecule benzothiazole hydrazones,” Antimicrob Agents Chemother, vol. 60, no. 7, pp. 4217-28, 2016.
  • [8] G. Negri, C. Kascheres, A. J. Kascheres, “Recent development in preparation reactivity and biological activity of enamino ketones and enamino thiones and their utilization to prepare heterocyclic compounds,” Journal of Heterocyclic Chemistry, vol. 41, no. 4, pp. 461-491, 2004.
  • [9] A. Hazra, S. Mondala, A. Maitya, S. Naskara, P. Sahaa, R. Pairaa, K. B. Sahua, P. Pairaa, S. Ghoshb, C. Sinhab, A. Samanta, S. Banerjeea, N. B. Mondal, “Amberlite–IRA-402 (OH) ion exchange resin mediated synthesis of indolizines, pyrrolo [1, 2-a] quinolines and isoquinolines: Antibacterial and antifungal evaluation of the products,” European Journal of Medicinal Chemistry, vol. 46, no. 6, pp. 2132-40, 2011.
  • [10] S. Saeed, N. Rashid, P. G. Jones, M. Ali, R. Hussain, “Synthesis, characterization and biological evaluation of some thiourea derivatives bearing benzothiazole moiety as potential antimicrobial and anticancer agents,” European Journal of Medicinal Chemistry, vol. 45, no. 4, pp. 1323-31, 2010.
  • [11] P. Zajdel, A. Partyka, K. Marciniec, A. J. Bojarski, M. Pawlowski, A. Wesolowska, “Quinoline-and isoquinoline-sulfonamide analogs of aripiprazole: novel antipsychotic agents?,” Future Medicinal Chemistry, vol. 6, no. 1, pp. 57-75, 2014.
  • [12] D. C. Liu, H. J. Zhang, C. M. Jin, Z. S. Quan, “Synthesis and biological evaluation of novel benzothiazole derivatives as potential anticonvulsant agents,” Molecules, vol. 21, no. 3, pp. 164, 2016.
  • [13] E. G. Paronikyan, A. S. Noravyan, S. F. Akopyan, I. A. Dzhagatspanyan, I. M. Nazaryan, R. G. Paronikyan, “Synthesis and anticonvulsant activity of pyrano [4′, 3′: 4, 5] pyrido [2, 3-b] thieno [3, 2-d] pyrimidine derivatives and pyrimido [5′, 4′: 2, 3]-thieno [2,3-c] isoquinoline derivatives,” Pharmaceutical Chemistry Journal, vol. 41, no. 9, pp. 466-9, 2007.
  • [14] S. Shafia, M. Mahboob, A. Naveen, M. Chaitanya, M. G. Vanajad, A. M. Kalled, R. Pallud, M.S.Alama, “Synthesis of novel 2-mercapto benzothiazole and 1,2,3-triazole based bis-heterocycles: their anti-inflammatory and anti-nociceptive activities,” European Journal of Medicinal Chemistry, vol. 49, no. 2012, pp. 324-33, 2012.
  • [15] V. S. Patilac, K. P. Nandreb, S. Ghoshd, V. J., Rao, B. A. Chopadede, B. Sridharf, S. V. Bhosaleg, S. V. Bhosaleab, “Synthesis, crystal structure and antidiabetic activity of substituted (E)-3-(Benzo[d]thiazol-2-ylamino)phenylprop-2-en-1-one,” European Journal of Medicinal Chemistry, vol. 59, no. 2013, pp. 304-9. 2013.
  • [16] E. Pitta, A. Geronikaki, S. Surmava, P. Eleftheriou, V. P. Mehta, E. V. Van der Eycken, “Synthesis and HIV-1 RT inhibitory action of novel (4/6-substituted benzo[d]thiazol-2-yl) thiazolidin-4-ones Divergence from the non-competitive inhibition mechanism,” Journal of Enzyme Inhibition and Medicinal Chemistry, vol. 28, no. 1, pp. 113-22, 2013.
  • [17] W. Krzysztof, R. Guryn, O. P. Zuiderveld, H. Timmerman, “Non-imidazole histamine H3 ligands, Part 2: new 2-substituted benzothiazoles as histamine H3 antagonists,” Archiv der Pharmazie, vol. 332, no. 11, pp. 389-98, 1999.
  • [18] K. J. Wilson, C. R. Illig, N. Subasinghe, J. B. Hoffman, M. J. Rudolph, R. Soll, C. J. Molloy, R. Bone, D. Green, T. Randall, M. Zhang, F. A. Lewandowski, Z. Zhou, C. Sharp, D. Maguire, B. Grasberger, R. L. DesJarlais, J. Spurlino, “Synthesis of thiophene-2-carboxamidines containing 2-aminothiazoles and their biological evaluation as urokinase inhibitors,” Bioorganic and Medicinal Chemistry Letters, vol. 11, no. 7, pp. 915-18, 2001.
  • [19] N. El-Ket, E. Kendjo, M. Thellier, L. Assoumou, V. Potard, A. Taieb, I. Tantaoui, E. Caumes, R. Piarroux, C. Roussel, P. Buffet, D. Costagliola, S. Jauréguiberry, “Propensity score analysis of artesunate versus quinine for severe imported Plasmodium falciparum malaria in France,” Clinical Infectious Diseases, vol. 70, no. 2, pp. 280-87, 2020.
  • [20] S. D’Alessandro, D. Scaccabarozzi, L. Signorini, F. Perego, D. P. Ilboudo, P., Ferrante, S. Delbue, “The use of antimalarial drugs against viral infection,” Microorganisms, vol. 8, no. 1, pp. 85, 2020.
  • [21] H. N. Karade, B. N. Acharya, M. Sathe, M. P. Kaushik, “Design, synthesis, and antimalarial evaluation of thiazole-derived amino acids,” Medicinal Chemistry Research, vol. 17, no. 1, pp. 19–29, 2008.
  • [22] P. Ghosh, M. J. Deka, A. K. Saikia, “Lewis acid mediated intramolecular C–O bond formation of alkanol-epoxide leading to substituted morpholine and 1, 4-oxazepane derivatives: total synthesis of (±) –viloxazinec,” Tetrahedron, vol. 72, no. 5, pp. 690-698, 2016.
  • [23] R. M. Abdel-Rahman “Role of uncondensed 1,2,4-triazine compounds and related heterobicyclic systems as therapeutic agents: a review,” Pharmazie, vol. 56, no. 1, pp. 18-22, 2001.
  • [24] A. R. Surray “4-Thiazolidones.IV. The preparation of some 3-alkylaminoalkyl-2-aryl derivatives,” Journal of the American Chemical Society, vol. 71, no. 10, pp. 3354–56, 1949.
  • [25] N. G. Voznesenskaia, O. I. Shmatova, M. M. Ilyin, M. M. Ilyin Jr, V. G. Nenajdenko, “Enantioselective synthesis of thiazole‐derived α‐perfluoroalkylated 5–7‐membered amines,” European Journal of Organic Chemistry, vol. 2019, no. 9, pp. 1893-903, 2019.
  • [26] N. Berber, M. Arslan, F. Vural, A. Ergun, N. Gençer, O. Arslan, “Synthesis of new series of thiazol‐(2(3H)‐ylideneamino) benzene- sulfonamide derivatives as carbonic anhydrase inhibitors,” Journal of Biochemical and Molecular Toxicology, vol. 34, no. 12, pp. e22596, 2020.
  • [27] N. Berber, M. Arslan, Ç. Bilen, Z. Sackes, N. Gencer, O. Arslan, “Synthesis and evaluation of new phthalazine substituted β-lactam derivatives as carbonic anhydrase inhibitors,” Russian Journal of Bioorganic Chemistry, vol. 41, no. 4 pp. 414-20, 2015.
  • [28] N. Berber “Synthesis of certain new morpholine derivatives bearing a thiazole moiety,” Sakarya University Journal of Science and Technology, vol. 23, no. 4, pp. 554-58, 2019.
  • [29] S. Kılıcaslan, M. Arslan, Z. Ruya, Ç. Bilen, A. Ergün, N. Gençer, O. Arslan, “Synthesis and evaluation of sulfonamide-bearing thiazole as carbonic anhydrase isoforms hCA I and hCA II,” Journal of Enzyme Inhibition and Medicinal Chemistry, vol. 31, no. 6, pp. 1300-1305, 2016.
  • [30] H. Saad “The synthesis of some new sulfur-bearing various heterocyclic systems derived from asymmetrical n,n′-disubstituted thiourea derivatives,” Phosphorus, Sulfur, and Silicon, vol. 181, no. 7, pp. 1557-1567, 2006.
  • [31] H. A. Abdel-Azız, H. S. El-Zahabi, K. M. Dawood, “Microwave-assisted synthesis and in-vitro anti-tumor activity of 1,3,4-triaryl-5-N-arylpyrazole carboxamides,” European Journal of Medicinal Chemistry, vol. 45, no. 6, pp. 2427-2432, 2010.
  • [32] H. M. Abumelha “Synthesis and antioxidant assay of new nicotinonitrile analogues clubbed thiazole, pyrazole and/or pyridine ring systems,” Journal of Heterocyclic Chemistry, vol. 57, no. 3, pp. 1011-1022, 2020.
  • [33] Y. Feng, X. Ding, T. Chen, L. Chen, F. Liu, X. Jia, X. Luo, X. Shen, K. Chen, H. Jiang, H. Wang, H. Liu, D. Liu, “Design, synthesis, and interaction study of quinazoline-2 (1 H)-thione derivatives as novel potential Bcl-xL inhibitors,” Journal of Medicinal Chemistry, vol. 53, no. 9, pp. 3465-3479, 2010.
  • [34] H. A. Morsy, A. H. Moustafa “A facile approach for synthesis of thiazines-, thiazoles-and triazoles-annulated 6-styryl-2-thiouracil derivative,” Journal of the Iranian Chemical Society, vol. 17, no. 1, pp. 119-125, 2020.
  • [35] M. Sathishkumar, S. Nagarajan, P. Shanmugavelan, M. Dinesh, A. Ponnuswamy, “A facile, rapid, one-pot regio/stereoselective synthesis of 2-iminothiazolidin-4-ones under solvent/ scavenger-free conditions,” Beilstein Journal of Organic Chemistry, vol. 9, no. 1, pp. 689-697, 2013.
  • [36] A. R. Sayed, S. M. Gomha, E. A. Taher, Z. A. Muhammad, H. R. El-Seedi, H. M. Gaber, M. M. Ahmed, “One-pot synthesis of novel thiazoles as potential anti-cancer agents,” Drug Design, Development and Therapy, vol. 14, no. 2020, pp. 1363, 2020.
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There are 43 citations in total.

Details

Primary Language English
Subjects Chemical Engineering
Journal Section Research Articles
Authors

Nurcan Berber 0000-0002-1595-585X

Project Number FHD-2020-3440
Publication Date August 31, 2022
Submission Date June 11, 2021
Acceptance Date June 15, 2022
Published in Issue Year 2022 Volume: 26 Issue: 4

Cite

APA Berber, N. (2022). Synthesis and Characterization of Thiazole Compounds in the Presence of Various Reagents, Catalysts and Solvents. Sakarya University Journal of Science, 26(4), 757-767. https://doi.org/10.16984/saufenbilder.950016
AMA Berber N. Synthesis and Characterization of Thiazole Compounds in the Presence of Various Reagents, Catalysts and Solvents. SAUJS. August 2022;26(4):757-767. doi:10.16984/saufenbilder.950016
Chicago Berber, Nurcan. “Synthesis and Characterization of Thiazole Compounds in the Presence of Various Reagents, Catalysts and Solvents”. Sakarya University Journal of Science 26, no. 4 (August 2022): 757-67. https://doi.org/10.16984/saufenbilder.950016.
EndNote Berber N (August 1, 2022) Synthesis and Characterization of Thiazole Compounds in the Presence of Various Reagents, Catalysts and Solvents. Sakarya University Journal of Science 26 4 757–767.
IEEE N. Berber, “Synthesis and Characterization of Thiazole Compounds in the Presence of Various Reagents, Catalysts and Solvents”, SAUJS, vol. 26, no. 4, pp. 757–767, 2022, doi: 10.16984/saufenbilder.950016.
ISNAD Berber, Nurcan. “Synthesis and Characterization of Thiazole Compounds in the Presence of Various Reagents, Catalysts and Solvents”. Sakarya University Journal of Science 26/4 (August 2022), 757-767. https://doi.org/10.16984/saufenbilder.950016.
JAMA Berber N. Synthesis and Characterization of Thiazole Compounds in the Presence of Various Reagents, Catalysts and Solvents. SAUJS. 2022;26:757–767.
MLA Berber, Nurcan. “Synthesis and Characterization of Thiazole Compounds in the Presence of Various Reagents, Catalysts and Solvents”. Sakarya University Journal of Science, vol. 26, no. 4, 2022, pp. 757-6, doi:10.16984/saufenbilder.950016.
Vancouver Berber N. Synthesis and Characterization of Thiazole Compounds in the Presence of Various Reagents, Catalysts and Solvents. SAUJS. 2022;26(4):757-6.

Sakarya University Journal of Science (SAUJS)