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Letters in Organic Chemistry

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ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

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Research Article

Design and Synthesis of Novel Heterocycles Utilizing 4,6-Dimethyl-1- ((4-methylthiazol-2-yl)amino)-2-oxo-1,2-dihydropyridine-3-carbonitrile

Author(s): Rita M. Borik*

Volume 21, Issue 11, 2024

Published on: 28 March, 2024

Page: [973 - 982] Pages: 10

DOI: 10.2174/0115701786292887240321082939

Price: $65

Abstract

Novel hydrazones 4, 5, and oxime 6 were produced from the reaction of ketone 3 with hydrazine, phenylhydrazine, and hydroxylamine HCl, respectively. One pot multicomponent reaction of chalcones 7a-c, 3-(1H-indol-3-yl)-3-oxopropanenitrile 8, and ammonium acetate in MeOH at reflux temperature gave 2-(1H-indol-3-yl)-nicotinonitrile derivatives 10-12. Additionally, a one-pot reaction of chalcone 7a, malononitrile or ethyl cyanoacetate, and ammonium acetate in AcOH at reflux temperature afforded 6-aminopyridine derivatives 13 and 14, respectively.

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[1]
Alizadeh, S.R.; Ebrahimzadeh, M.A. Mini Rev. Med. Chem., 2021, 21(17), 2584-2611.
[http://dx.doi.org/10.2174/18755607MTEzvNjcu0] [PMID: 33573543]
[2]
Attaby, F.A.; Eldin, S.M.; Razik, M.A. Phosphorus Sulfur Silicon Relat. Elem., 1995, 106(1-4), 21-28.
[http://dx.doi.org/10.1080/10426509508027885]
[3]
Khidre, R.E.; Abdel-Wahab, B.F. Curr. Org. Chem., 2013, 17, 430-445.
[http://dx.doi.org/10.2174/1385272811317040009]
[4]
Balasubramanian, M.; Keay, J.G. Comprehensive Heterocyclic Chemistry; 2nd ed; Katritzky, A.R.; Rees, C.W.; Scriven, E.F.V., Eds.; Pergamon: Oxford, 1996, Vol. 5, p. 245.
[5]
Altaf, A.A.; Shahzad, A.; Gul, Z.; Rasool, N.; Badshah, A.; Lal, B.; Khan, E.J. Drug Design. Med. Chem., 2015, 1, 1-11.
[http://dx.doi.org/10.11648/j.jddmc.20150101.11]
[6]
De, S.; Kumar, SK A.; Shah, S.K.; Kazi, S.; Sarkar, N.; Banerjee, S.; Dey, S. RSC Advances, 2022, 12(24), 15385-15406.
[http://dx.doi.org/10.1039/D2RA01571D] [PMID: 35693235]
[7]
Hamada, Y. In: Pyridine; BoD- Books on Demand, IntechOpen: London, 2018, pp. 9-26.
[http://dx.doi.org/10.5772/intechopen.74719]
[8]
Sahu, R.; Mishra, R.; Kumar, R.; Majee, C. Indian J. Pharm. Sci., 2021, 83, 162-185.
[9]
Dai, H.; Huang, M.; Qian, J.; Liu, J.; Meng, C.; Li, Y.; Ming, G.; Zhang, T.; Wang, S.; Shi, Y.; Yao, Y.; Ge, S.; Zhang, Y.; Ling, Y. Eur. J. Med. Chem., 2019, 166, 470-479.
[http://dx.doi.org/10.1016/j.ejmech.2019.01.070] [PMID: 30739827]
[10]
Mohamed, E.A.; Ismail, N.S.M.; Hagras, M.; Refaat, H.; Future, J. Pharma. Sci., 2021, 7(1), 24.
[http://dx.doi.org/10.1186/s43094-020-00165-4]
[11]
Aliabadi, A.; Motieiyan, E.; Hosseinabadi, F.; Ghadermazi, M.; Abdolmaleki, S. J. Mol. Struct., 2021, 1226, 129405.
[http://dx.doi.org/10.1016/j.molstruc.2020.129405]
[12]
Chen, Y.J.; Huang, S.M.; Tai, M.C.; Chen, J.T.; Lee, A.R.; Huang, R.Y.; Liang, C.M. Pharmacol. Rep., 2020, 72(1), 115-125.
[http://dx.doi.org/10.1007/s43440-019-00026-9] [PMID: 32016832]
[13]
Ali, E.M.H.; Abdel-Maksoud, M.S.; Hassan, R.M.; Mersal, K.I.; Ammar, U.M.; Se-In, C.; He-Soo, H.; Kim, H.K.; Lee, A.; Lee, K.T.; Oh, C.H. Bioorg. Med. Chem., 2021, 31, 115969.
[http://dx.doi.org/10.1016/j.bmc.2020.115969] [PMID: 33422910]
[14]
Bass, A.; Abdelhafez, E.; El-Zoghbi, M.; Mohamed, M.; Badr, M.; Abuo-Rahma, G.E.D.J. advan. Biom. Pharma. Sci., 2021, 4(2), 81-86.
[http://dx.doi.org/10.21608/jabps.2020.52641.1113]
[15]
Hammoudi, N.E.H.; Benguerba, Y.; Attoui, A.; Hognon, C.; Lemaoui, T.; Sobhi, W.; Benaicha, M.; Badawi, M.; Monari, A. J. Biomol. Struct. Dyn., 2022, 40(2), 886-902.
[http://dx.doi.org/10.1080/07391102.2020.1819878] [PMID: 32948119]
[16]
Sugiyama, S.; Akiyama, T.; Taoda, Y.; Iwaki, T.; Matsuoka, E.; Akihisa, E.; Seki, T.; Yoshinaga, T.; Kawasuji, T. Bioorg. Med. Chem. Lett., 2021, 33, 127742.
[http://dx.doi.org/10.1016/j.bmcl.2020.127742] [PMID: 33316407]
[17]
Fraser, H.L.; Floyd, M.B.; Sosa, A.C.B. In: Progress in Heterocyclic Chemistry; Gribble, G.W.; Joule, J.A., Eds.; Elsevier, 2005, Vol. 17, pp. 261-303.
[18]
Song, P.; Hu, L.; Yu, T.; Jiao, J.; He, Y.; Xu, L.; Li, P. ACS Catal., 2021, 11(12), 7339-7349.
[http://dx.doi.org/10.1021/acscatal.1c01671]
[19]
da S Souza L.G.; Almeida, M.C.S.; Lemos, T.L.G.; Ribeiro, P.R.V.; de Brito, E.S.; Silva, V.L.M.; Silva, A.M.S.; Braz-Filho, R.; Costa, J.G.M.; Rodrigues, F.F.G.; Barreto, F.S.; de Moraes, M.O. Bioorg. Med. Chem. Lett., 2016, 26(2), 435-439.
[http://dx.doi.org/10.1016/j.bmcl.2015.11.095] [PMID: 26684850]
[20]
Akki, M.; Reddy, D.S.; Katagi, K.S.; Kumar, A.; Devarajegowda, H.C.; Kumari, M. ChemistrySelect, 2022, 7, e202203260.
[http://dx.doi.org/10.1002/slct.202203260]
[21]
Patel, A.K.; Jadeja, R.N.; Roy, H.; Patel, R.N.; Patel, S.K.; Butcher, R.J.; Cortijo, M.; Herrero, S. Polyhedron, 2020, 186, 114624.
[http://dx.doi.org/10.1016/j.poly.2020.114624]
[22]
Peng, Z.; Wang, G.; Zeng, Q.H.; Li, Y.; Wu, Y.; Liu, H.; Wang, J.J.; Zhao, Y. Food Chem., 2021, 341(Pt 2), 128265.
[http://dx.doi.org/10.1016/j.foodchem.2020.128265] [PMID: 33031957]
[23]
Elmansy, M.F.; Borik, R.M.; Khidre, R.E. Curr. Org. Chem., 2023, 27(5), 444-459.
[http://dx.doi.org/10.2174/1385272827666230512114730]
[24]
Hussein, M.A.; Borik, R.M. Curr. Pharm. Biotechnol., 2022, 23(9), 1179-1203.
[http://dx.doi.org/10.2174/1389201022666210601170650] [PMID: 34077343]
[25]
Borik, R.M.; Hussein, M.A. Asian J. Chem., 2021, 33(2), 423-438.
[http://dx.doi.org/10.14233/ajchem.2021.23036]
[26]
Borik, R.M. Curr. Org. Chem., 2023, 27(22), 1960-1977.
[http://dx.doi.org/10.2174/0113852728278212231215045922]
[27]
Khidre, R.E.; Radini, I.A.M. Sci. Rep., 2021, 11(1), 7846.
[http://dx.doi.org/10.1038/s41598-021-86424-7] [PMID: 33846389]

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