Microwave irradiated synthesis of Schiff bases of 4-(arylideneamino)-5-alkyl-2,4- dihydro-1,2,4-triazole-3-thione containing 1,2,4-triazole segment

Microwave irradiated synthesis of Schiff bases of 4-(arylideneamino)-5-alkyl-2,4- dihydro-1,2,4-triazole-3-thione containing 1,2,4-triazole segment

Novel compounds based on the 1,2,4-triazole skeleton were synthesized. A class of 4-amino-5-alkyl-4H-1,2,4-triazole-3- thione created by reaction of thiocarbohydrazide with long-chain aliphatic carboxylic acids, and then the Schiff bases were obtained in the media of heat and microwave waves, in the presence and the absence of a catalyst. Their chemical structures were assayed by elemental analysis, also device spectroscopic methods.

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  • 1. Behalo MS, Gad El-karim IA, Issac YA, Farag MA. Synthesis of novel pyridazine derivatives as potential antimicrobial agents. Journal of Sulfur Chemistry 2014; 35 (3): 661-673. doi: 10.1080/17415993.2014.950661
  • 2. Mishra R, Kumar R, Kumar S, Majeed J, Rashid M et al. Synthesis and in vitro antimicrobial activity of some triazole derivatives. Journal of the Chilean Chemical Society 2010; 55 (3): 359-362. doi: 10.4067/S0717-97072010000300019
  • 3. Karabasanagouda T, Adhikari AV, Shetty NS. Synthesis and antimicrobial activities of some novel 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazoles and 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazines carrying thioalkyl and sulphonyl phenoxy moieties. European Journal of Medicinal Chemistry 2007; 42 (4): 521-529. doi: 10.1016/j.ejmech.2006.10.010
  • 4. Patil BS, Krishnamurthy G, Shashikumar ND, Lokesh MR, Naik HSB. Synthesis and antimicrobial activity of some [1,2,4]-triazole derivatives. Journal of Chemistry 2013; 1-7. doi: 10.1155/2013/462594
  • 5. Li C, Liu JC, Li YR, Gou C, Zhang ML et al. Synthesis and antimicrobial evaluation of 5-aryl-1, 2, 4-triazole-3-thione derivatives containing a rhodanine moiety. Bioorganic & Medicinal Chemistry Letters 2015; 25 (15): 3052-3056. doi: 10.1016/j.bmcl.2015.04.081
  • 6. Popiołek L, Biernasiuk A, Paruch K, Paruch K, Patrejko P, Wujec M. Synthesis and evaluation of antimicrobial properties of new Mannich bases of 4,5-disubstituted-1,2,4-triazole-3-thiones. Phosphorus, Sulfur, and Silicon and the Related Elements 2017; 192 (7): 880–885. doi: 10.1080/10426507.2017.1290629
  • 7. El-Serwy WS, Mohamed NA, Abbas EM, Abdel-Rahman RF. Synthesis and anti-inflammatory properties of novel 1,2,4-triazole derivatives. Research on Chemical Intermediates 2013; 39 (6): 2543–2554. doi: 10.1007/s11164-012-0781-9
  • 8. Hussein MA, Shaker RM, Ameen MA, Mohammad MF. Synthesis, anti-inflammatory, analgesic, and antibacterial activities of some triazole, triazolothiadiazole, and triazolothiadiazine derivatives. Archives of Pharmacal Research 2011; 34 (8): 1239-1250. doi: 10.1007/ s12272-011-0802-z
  • 9. El-Shehry MF, Abu-Hashem AA, El-Telbani EM. Synthesis of 3-((2,4-dichlorophenoxy)methyl)-1,2,4-triazolo (thiadiazoles and thiadiazines) as anti-inflammatory and molluscicidal agents. European Journal of Medicinal Chemistry 2010; 45 (5): 1906–1911. doi: 10.1016/j.ejmech.2010.01.030
  • 10. Romagnoli R, Baraldi PG, Salvador MK, Prencipe F, Bertolasi V et al. Synthesis, antimitotic and antivascular activity of 1-(3′,4′,5′-trimethoxybenzoyl)-3-arylamino-5-amino-1,2,4-triazoles. Journal of Medicinal Chemistry 2014; 57 (15): 6795−6808. doi: 10.1021/jm5008193
  • 11. Husain A, Naseer MA, Sarafroz M. Synthesis and anticonvulsant activity of some novel fused heterocyclic 1,2,4-triazolo-[3,4-b]-1,3,4- thiadiazole derivatives. Acta Poloniae Pharmaceutica2009; 66 (2): 135-140. pmid: 19719046
  • 12. Kamal A, Khan MNA, Reddy KS, Srikanth YVV, Sridhar B. Synthesis, structural characterization and biological evaluation of novel [1,2,4] triazolo[1,5-b][1,2,4]benzothiadiazine-benzothiazole conjugates as potential anticancer agents. Chemical Biology & Drug Design 2008; 71 (1): 78–86. doi: 10.1111/j.1747-0285.2007.00609.x
  • 13. Joshi SD, Vagdevi HM, Vaidya VP, Gadaginamath GS. Synthesis of new 4-pyrrol-1-yl benzoic acid hydrazide analogs and some derived oxadiazole, triazole and pyrrole ring systems: A novel class of potential antibacterial and antitubercular agents. European Journal of Medicinal Chemistry 2008; 43 (9): 1989-1996. doi: 10.1016/j.ejmech.2007.11.016
  • 14. Ghammamy S, Sedaghat S. Synthesis, Characterization, and antitumor activity of azomethine derivative of triazole and its complexes with copper(I) and zinc(II) salts. Russian Journal of General Chemistry 2013; 83 (4): 722–725. doi: 10.1134/S1070363213040191
  • 15. Ibrahim DA. Synthesis and biological evaluation of 3,6-disubstituted [1,2,4]triazolo[3,4-b][1,3,4]thiadiazole derivatives as a novel class of potential anti-tumor agents. European Journal of Medicinal Chemistry 2009; 44 (7): 2776–2781. doi: 10.1016/j.ejmech.2009.01.003
  • 16. Maqsood MR, Hanif M, Rafiq M, Saleem M, Ziba S et al. Some pyridyl- and thiophenyl- substituted 1,2,4-triazolo[3,4-b]1,3,4-thiadiazole derivatives as potent antibacterial. Bulletin of the Korean Chemical Society 2012; 33 (12): 4180-4184. doi: 10.5012/bkcs.2012.33.12.4180
  • 17. Plech T, Wujec M, Kosikowska U, Malm A, Kapron B. Studies on the synthesis and antibacterial activity of 3,6-disubstituted 1,2,4-triazolo[3,4-b]1,3,4-thiadiazoles. European Journal of Medicinal Chemistry 2012; 47: 580-584. doi: 10.1016/j.ejmech.2011.10.055
  • 18. Tee EHL, Karoli T, Ramu S, Huang JX, Butler MS et al. Synthesis of essramycin and comparison of its antibacterial activity. Journal of Natural Products 2010; 73 (11): 1940–1942. doi: 10.1021/np100648q
  • 19. Yang J, Zhao Z, Li H. Synthesis using microwave irradiation, characterisation and antibacterial activity of novel deoxycholic acid-triazole conjugates. Journal of Chemical Research 2012; 36 (7): 383–386. doi: 10.3184/174751912X13364636691591
  • 20. Joshi R, Pandey N, Yadav SK, Tilak R, Mishra H et al. Synthesis, spectroscopic characterization, DFT studies and antifungalactivity of (E)-4-amino-5-[N’-(2-nitro-benzylidene)-hydrazino]-2,4-dihydro-[1,2,4]triazole-3-thione. Journal of Molecular Structure 2018; 1164: 386-403. doi: 10.1016/j.molstruc.2018.03.081
  • 21. Mares D, Romagnoli C, Andreotti E, Manfrini M, Vicentini CB. Synthesis and antifungal action of new tricyclazole analogues. Journal of Agricultural and Food Chemistry 2004; 52 (7): 2003-2009. doi: 10.1021/jf030695y
  • 22. Wang BL, Zhan YZ, Zhang LY, Zhang Y, Zhang X et al. Synthesis and fungicidal activities of novel 1,2,4-triazole thione derivatives containing 1,2,3-triazole and substituted piperazine moieties. Phosphorus, Sulfur, and Silicon and the Related Elements 2015; 191 (1): 1–7. doi: 10.1080/10426507.2015.1085040
  • 23. Xu Q, Sun M, Bai Z, Wang Y, Wu Y et al. Design, synthesis and bioevaluation of antitubulin agents carrying diaryl-5,5-fused-heterocycle scaffold. European Journal of Medicinal Chemistry 2017; 139: 242–249. doi: 10.1016/j.ejmech.2017.05.065
  • 24. Hull JW, Romer DR, Adaway TJ, Podhorez DE. Development of manufacturing processes for a new family of 2,6-dihaloaryl1,2,4-triazole insecticides. Organic Process Research & Development 2009; 13 (6): 1125–1129. doi: 10.1021/op9001577
  • 25. Ma Y, Liu R, Gong X, Li Z, Huang Q et al. Synthesis and herbicidal activity of N,N-Diethyl-3-(arylselenonyl)-1H-1,2,4-triazole-1- carboxamide. Journal of Agricultural and Food Chemistry 2006; 54 (20): 7724-7728. doi: 10.1021/jf0609328
  • 26. Kumar MS, Kumar SLA, Sreekanth A. Anticorrosion potential of 4-Amino-3-methyl-1,2,4-triazole-5-thione derivatives (SAMTT and DBAMTT) on mild steel in hydrochloric acid solution. Industrial & Engineering Chemistry Research 2012; 51 (15): 5408−5418. doi: 10.1021/ie203022g
  • 27. Azizian J, Soozangarzadeh S, Jadidi K. Microwave-induced one-pot systhesis of some new spiro[3H-indol-3,5′(4′H)-[1,2,4]- triazoline]- 2-ones. Synthetic Communications 2001; 31 (7): 1069-1073. doi: 10.1081/SCC-100103539
  • 28. Azizian J, Varasteh-Morady A, Soozangarzadeh S, Asadi A. Synthesis of novel spiro-[3H-indole-3,3′-[1,2,4]triazolidine]-2-ones via azomethine imines. Tetrahedron Letters 2002; 43 (52): 9721-9723. doi: 10.1016/S0040-4039(02)02061-0
  • 29. Azizian J, Madani M, Souzangarzadeh S. One-pot synthesis of novel derivatives of spiro-[6H-indolo [2,1-b]quinazoline-6,3′-[1,2,4] oxadiazoline]. Synthetic Communications 2005; 35 (6): 765. doi: 10.1081/scc-200050932
  • 30. Souzangarzadeh S, Bazian A, Anaraki-Ardakani H. A facile synthesis of novel spiro indoline-based heterocycles through 1,3-dipolar cycloaddition reactions. Journal of Chemical Research 2012; 36 (2): 94-95. doi: 10.3184/174751912X13279492179667
  • 31. Hajiaghababaei L, Sharafi A, Suzangarzadeh S, Faridbod F. Mercury Recognition: A Potentiometric Membrane Sensor based on 4-(Benzylidene amino)-3,4-dihydro-6- methyl-3-thioxo-1,2,4-triazin-5(2H)one. Analytical and Bioanalytical Chemistry 2013; 5 (4): 481- 493.
  • 32. Souzangarzadeh S. 1,3-Dipolar cycloaddition reaction of nitrile oxides to isatin imines. Iranian Journal of Chemistry and Chemical Engineering 2016; 35 (1): 31-35. doi: 10.30492/IJCCE.2016.18804
  • 33. Hajiaghababaei L, Zandinejad S, Berijani S, Suzangarzadeh S. Ultrasound assisted emulsification microextraction for selective determination of trace amount of mercury(II). Indian Journal of Chemistry 2016; 55: 423-428.
  • 34. Sharifi A, Hajiaghababaei L, Suzangarzadeh S, Jalali-Sarvestani MR. Synthesis of 3-((6-methyl-5-oxo-3-thioxo-2,5-dihydro-1,2,4-triazin4(3H)-yl)imino)indolin-2-one as an excellent ionophore to the construction of a potentiometric membrane sensor for rapid determination at zinc. Analytical & Bioanalytical Electrochemistry 2017; 9 (7): 888-9033.
Turkish Journal of Chemistry-Cover
  • ISSN: 1300-0527
  • Yayın Aralığı: 6
  • Yayıncı: TÜBİTAK
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