Intramolecular Heterocyclization of Quinolyl-Substituted Carbotiamides Into Functionalized 2,4-Dihydro-3H-1,2,4-triazoles and 1,3,4-Thiadiazoles
- Autores: Aleksanyan I.L.1, Hambardzumyan L.P.1
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Afiliações:
- Yerevan State University
- Edição: Volume 60, Nº 8 (2024)
- Páginas: 39-43
- Seção: Articles
- URL: https://modernonco.orscience.ru/0514-7492/article/view/676683
- DOI: https://doi.org/10.31857/S0514749224080058
- EDN: https://elibrary.ru/RAKBJQ
- ID: 676683
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Resumo
An economical and straightforward approach has been introduced for the transformation of quinolyl-substituted propanoyl-N-phenylhydrazine-1-carbothioamide into quinolone derivatives encompassing 4-phenyl-2,4-dihydro-3H-1,2,4-triazole-3-thiones and 1,3,4-thiadiazoles through a heterocyclization reaction using a water solution of sodium hydroxide and concentric sulfuric acid. This efficient procedure has proven to yield the desired products with high efficiency (85—98%). The protocol offers advantages such as cost-effectiveness, omission of catalyst or column chromatography, mild reaction conditions, elevated yields.
Texto integral

Sobre autores
I. Aleksanyan
Yerevan State University
Autor responsável pela correspondência
Email: ialeksanyan@ysu.am
ORCID ID: 0000-0002-4039-2323
Armênia, Yerevan
L. Hambardzumyan
Yerevan State University
Email: ialeksanyan@ysu.am
ORCID ID: 0000-0003-1210-0052
Armênia, Yerevan
Bibliografia
- Aly A.A., Hassan A.A., Makhlouf M.M., Bräse S. Molecules. 2020, 25, 3036. doi: 10.3390/molecules25133036
- Zhang S.S., Tan Q.W., Guan L.P., Mini Rev Med Chem. 2021, 21, 16, 2261–2275. doi: 10.2174/1389557521666210111145011
- Matada B.S., Pattanashettar R., Yernale N.G., Bioorg Med Chem. 2021, 32, 115973(1–25). doi: 10.1016/j.bmc.2020.115973
- Bin Y., Xiuyan Y. Chem Biol Drug Des. 2022, 100, 6, 763–765. doi: 10.1111/cbdd.14166
- Paranjeet K., Anuradha A.C., Tamanna T., Kumar S.S., Amit M. Chem Biol Drug Des. 2022, 100, 6, 765–785. doi: 10.1111/cbdd.14025
- Khidre R., Salem M.A., Ameen T.A., Abdelgawad A.A.M. Polycycl. Aromatic Compd. 2023, 43, 1, 13–53. doi: 10.1080/10406638.2021.2008457
- Jamshidi H., Naimi-Jamal M.R., Safavi M., Rayat Sanati K., Azerang P., Tahghighi A. Amit. Chem. Biol. Drug Des. 2022, 100, 6, 935–946. doi: 10.1111/cbdd.14031
- Abdi B., Fekadu M., Zeleke D., Eswaramoorthy R., Melaku Y. J. Chem. 2021, 2408006(1–13). doi: 10.1155/2021/2408006
- Gupta S.K., Mishra A. Agents Med. Chem. 2016, 15, 31–43. doi: 10.2174/1871523015666160210124545
- Zajdel P., Marciniec K., Maślankiewicz A., Grychowska K., Satała G., Duszyńska, B., Lenda T., Siwek A., Nowak G., Partyka A., Wróbel D., Jastrzębska-Więsek M., Bojarski A.J., Wesolowska A., Pawłowski M. Eur. J. Med. Chem. 2013, 60, 42–50. doi: 10.1016/j.ejmech.2012.11.042
- Kumar H., Devaraji V., Joshi R., Jadhao M., Ahirkar P., Prasath R., Bhavana P., Ghosh, S.K. RSC Adv. 2015, 5, 65496–65513. doi: 10.1039/C5RA08778C
- Shang, X.F. Morris-Natschke, S.L. Liu, X. Guo, Y.Q. Xu, M. Goto, X.S. Li, J.C.. Yang, G.Z Lee, K.H. Med. Res. Rev. 2018, vol. 38, p. 775–828. doi: 10.1002/med.21466
- Senerovic, L. Opsenica, D. Moric, I. Aleksic, I. Spasić, M. Vasiljevic, B. Adv. Experim. Med. Biol. 2019, vol. 1282, p. 37-69. doi: 10.1007/5584_2019_428
- Shruthi T. G., Eswaran S., Shivarudraiah P., Narayanan S., Subramanian S. Bioorg. Med. Chem. Lett. 2019, 29, 97–102. doi: 10.1016/j.bmcl.2018.11.002
- Kaur T., Bhandari D.D Biointerface Res. Appl. Chem. 2023, 13, 4, 355(1–19). doi: 10.33263/BRIAC134.355
- Kaur R., Kumar K. Eur. J. Med. Chem. 2021, 215, 113220(1–36). doi: 10.1016/j.ejmech.2021.113220
- Bekhit A.A., Nasralla S.N., El-Agroudy E.J., Hamouda N., El-Fattah A.A., Bekhit S.A., Amagase K., Ibrahim T.M. Eur. J Pharm. Sci. 2022, 168, 106080(1–10).
- doi: 10.1016/j.ejps.2021.106080
- Tornheim J.A., Udwadia Z.F., Arora P.R., Gajjar I., Sharma S., Karane M., Sawant N., Kharat N., Blum A.J., Shivakumar S.V.B.Y., Gupte A.N., Gupte N., Mullerpattan J.B., Pinto L.M., Ashavaid T.F., Gupta A., Rodrigues C. Open Forum Infectious Diseases. 2022, 9, 2, ofab615. doi: 10.1093/ofid/ofab615
- Kucharski D.J., Jaszczak M.K., Boratynski P.J. Molecules. 2022, 27, 1003(1–34). doi: 10.3390/molecules27031003
- Zhang J., Lei X., Tang J., Chen J., Zhao Q., Fang W., Zhang Y., Li Y., Zuo Y.J. BionicEng. 2022, 19, 483–496. doi: 10.1007/s42235-021-00144-2
- Morley C., Carvalho de Almeida C., Moloney S., Grimwood K., Infect. Dis. J. 2022, 41, 121–122. doi: 10.1097/INF.0000000000003373
- Coyle M.A., Goss C.S., Manz W.J., Greenshields J.T., Chapman R.F., Stager J.M., Physiol. Rep. 2022, 10, e15149(1–11). doi: 10.14814/phy2.15149
- Kulkarni A.V., Tirumalle S., Premkumar M., Kumar K., Fatima S., Rapole B., Simhadri, V. Gora B.A., Sasikala M., Gujjarlapudi D., Yelamanchili S., Sharma M., Gupta R., Rao P.N., reddy D.N. Am. J. Gastroenterol. 2022, 117, 607–616. doi: 10.14309/ajg.0000000000001611
- Yang H., Park T., Park D., Kang M.G., Toxicol. Vitro. 2022, 82, 05374(1–9). doi: 10.1016/j.tiv.2022.105374
- Voss F.O., van Beurden M.V., Jordanova E.S., Lancet. 2022, 399, 1755–1757. doi: 10.1016/S0140-6736(22)00624-9
- Aleksanyan I.L., Hambardzumyan L.P., Russ J Org Chem. 2017, 53, 226–230. doi: 10.1134/S1070428017020142
- Aleksanyan I.L., Hambardzumyan L.P., Russ J Org Chem. 2018, 54, 1402–1405. doi: 10.1134/S1070428018090221
- Aleksanyan I.L., Hambardzumyan L.P., Russ J Org Chem. 2019, 55, 262–265. doi: 10.1134/S1070428019020209
- Batista F.V., Pinto D.C.G.A., Silva, A.M.S. ACS Sustainable Chem. Eng. 2016, 4, 8, 4064–4078. doi: 10.1021/acssuschemeng.6b01010
- Patel A., Patel S., Mehta M., Patel Y., Patel R., Shah D., Patel D., Shah U., Patel M., Patel S., Solanki N., Bambharoliya T., Patel S., Nagani A., Patel H., Vaghasiya J., Shah H., Prajapati B., Rathod M., Bhimani B., Patel R., Bhavsar V., Rakholiya B., Patel M., Patel P. Green chemistry letters and reviews. 2022, 15, 2, 337–372. doi: 10.1080/17518253.2022.2064194
- Nainwal L.M., Tasneem S., Akhtar W., Verma G., Khan M.F., Parvez S., Shaquiquzzaman M., Akhter M., Alam M.M. EUR. J. Med. Chem. 2019, 164, 121–170. doi: 10.1016/j.ejmech.2018.11.026
- Tanaka K., Toda F., Chemical Review. 2000, 100, 1025–1074. doi: 10.1021/cr940089p
- Shaikh I.R. Journal of Catalysts. 2014. 402860(1–35). doi: 10.1155/2014/402860
- Clark J. H., Nat. Chem. 2009, 1, 1, 12–13. doi: 10.1038/nchem.146
- Song J., Han B., Natl. sci. Rev. 2015, 2, 3, 255–256. doi: 10.1093/nsr/nwu076
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