Amaç: Bu çalışmanın amacı, Milestone Flexi Wave mikrodalga sentez sistemi ile 3-(alkiltiyo)-5-(tiyofen-2-ilmetil)-1,2,4-triazol-4-aminlerin sentezlenmesi ve sentezlenen bileşiklerin yapısının onaylanmasıdır. Gereç ve Yöntem: İlk bileşikler 3-(tiyofen-2-ilmetil)-4H-1,2,4-triazol-5-tiyoller (1-5) Zaporizhzhya State Medical Üniversite Toksikolojik ve İnorganik Kimya Anabilim Dalı'nda sentezlendi (Ukrayna). 3-(alkiltiyo)-5-(tiyofen-2-ilmetil)-1,2,4-triazol-4-aminlerin sentezlenmesi için Milestone Flexi Wave mikrodalga sentez sistemi kullanıldı. Sentezlenen
bileşiklerin element analizi evrensel analiz Elementar Vario L küpü (CHNS)
tarafından yapıldı. 1H spektrumları (400 MHz ve 100 MHz'de), DMSO-d6'da
bir Varian MR-400 spektrometresi üzerinde kaydedildi ve ADVASP ™ Analyzer
programı ile analiz edildi. Reaksiyonlar ve elde edilen bileşikler, bir 5977B
kütle spektrometre detektörü ile Agilent 7890B gaz kromatografısinde kontrol edildi.Sonuç
ve Tartışma:
Reaksiyon, 5-(tiyofen-2-ilmetil)-4H-1,2,4-triazol-3-tiyollere katalitik
miktarda HCI ilave edilerek alkollü bir ortamda gerçekleştirildi. Alkol olarak
metil ve i-propil alkoller kullanıldı. Karışım, 45 dakika boyunca 150°C
sıcaklıkta, 14.4 bar basınçta, ΔMW = 200 W sıcaklıkta ısıtıldı.
Çözücü olarak asetik asit
kullanıldı. (4a-b, 6a-j) için önerilen yapı, 1H
NMR sinyalleri ile doğrulandı. Temel
kimyasal yapılarını doğrulamak için sentezlenen bileşikler üzerinde element
analizi (CHNS) yapıldı ve hesaplanan yüzdelerle kabul edilebilir bir uyum
sağladığını gösterdi.
Objectives: The purpose of this work is to synthesize N-R-3-(alkylthio)-5-(thiophen-2-ylmethyl)-1,2,4-triazol-4-amines
by the Milestone Flexi Wave microwave synthesis system and to prove structure
synthesized compounds.Materials and Methods: The initial compounds 4-R1-3-(thiophen-2-ylmethyl)-4H-1,2,4-triazole-5-thioles
(1-5) were synthesized at the Department of Toxicological and Inorganic
Chemistry of the Zaporizhzhya State Medical University (Ukraine ). Milestone Flexi Wave microwave synthesis system was
used to synthesize
N-R-3-(alkylthio)-5-(thiophen-2-ylmethyl)-1,2,4-triazol-4-amines. The
elemental analysis of synthesized compounds was established by the universal
analyzer Elementar Vario L cube (CHNS). The 1H spectra (at 400 MHz and 100 MHz)
were recorded in DMSO-d6 on a Varian MR-400 spectrometer and analysed with
ADVASP™ Analyzer program. The completeness of the reactions and the
individuality of the resulting compounds were controlled by the gas
chromatograph Agilent 7890B with a 5977B mass spectrometry detector.Result and Discussion: The reaction was carried out in an
alcoholic medium by adding a catalytic amount of HCl to 4-R-5-(thiophen-2-ylmethyl)-4H-1,2,4-triazole-3-thiols.
Methyl and i-propyl alcohols were used as alcohols. The mixture was heated for
45 minutes at a temperature of 150 ° C, a pressure 14.4 bar, ΔMW = 200 W.The signals of 1H NMR for (4a-b, 6a-j) are consented with the proposed
structure.
The elemental analysis (CHNS) was accomplished for synthesized compounds
to confirm their basic chemical structures and revealed acceptable agreement
with the calculated percentages.
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Arnold, F. H. (2018). Directed Evolution: Bringing New Chemistry To Life. Angewandte Chemie International Edition, 57(16), 4143-4148.
Gerry, C. J., & Schreiber, S. L. (2018). Chemical Probes And Drug Leads From Advances In Synthetic Planning And Methodology. Nature Reviews Drug Discovery, 17(5), 333.
Minozzi, C., Caron, A., Grenier‐Petel, J. C., Santandrea, J., & Collins, S. K. (2018). Heteroleptic Copper (I)‐Based Complexes for Photocatalysis: Combinatorial Assembly, Discovery, and Optimization. Angewandte Chemie International Edition, 57(19), 5477-5481.
Shcherbyna, R. O., Danilchenko, D. M., Parchenko, V. V., Panasenko, O. I., Knysh, E. H., Hromyh, N. A., & Lyholat, Y. V. (2017). Studying Of 2-((5-R-4-R-1-4H-1,2,4-triazole-3-yl)thio)acetic Acid Salts Influence On Growth And Progress Of Blackberries (KIOWA Variety) Propagules. Research Journal of Pharmaceutical Biological and Chemical Sciences, 8(3), 975-979.
Shcherbyna, R. O., Parchenko, V. V., Safonov, A. A., Bushueva, I. V., Zazharskiy, V. V., Davydenko, P. O. & Borovic, I. V. (2018). Synthesis And Research Of The Impact Of New Derivatives Of 4-R-3-(Morpholinomethyl)-4H-1,2,4-Triazole-5-thiol On Cultural Attributes Of Pathogenic M. Bovis. Research Journal of Pharmaceutical Biological and Chemical Sciences, 9(2), 70-79.
Samelyuk, Y. G., & Kaplaushenko, A. G. (2014). Synthesis Of 3-Alkylthio(sulfo)-1,2,4-triazoles, Containing Methoxyphenyl Substituents At C5atoms, Their Antipyretic Activity, Propensity To Adsorption And Acute Toxicity. Journal of Chemical and Pharmaceutical Research, 6(5), 1117-1121.
Mermer, A., Demirbaş, N., Şirin, Y., Uslu, H., Özdemir, Z., & Demirbaş, A. (2018). Conventional And Microwave Prompted Synthesis, Antioxidant, Anticholinesterase Activity Screening And Molecular Docking Studies Of New Quinolone-Triazole Hybrids. Bioorganic chemistry, 78, 236-248.
Basoglu Ozdemir, S., Demirbas, N., Demirbas, A., Ayaz, F. A., & Çolak, N. (2018). Microwave‐Assisted Synthesis, Antioxidant, and Antimicrobial Evaluation of Piperazine‐Azole‐Fluoroquinolone Based 1,2,4‐Triazole Derivatives. Journal of Heterocyclic Chemistry, 55(12), 2744-2759.
Rud, A. M., Kaplaushenko, A. G., Pruglo, Y. S., & Frolova, Y. S. (2018). Establishment Of Diuretic Activity Indicators For (3-Thio-4-R-4-H-1,2,4-triazole-5-yl)(phenyl)methanols And Their Derivatives. Aktualʹnì Pitannâ Farmacevtičnoï ì Medičnoï Nauki ta Praktiki, 2018(2), 215-219.
Hulina, Y.S., & Kaplaushenko, A. G. (2018). Synthesis, Physicochemical Properties And Further Transformations In The Series 5-((1H-tetrazol-1-yl)methyl)-4-R-4H-1,2,4-triazol-3-thiols. Biopharmaceutical Journal, 10 (1), 26-30.
Ignatova, T. V., Kaplaushenko, A. H., & Frolova, Y. S. (2018). The Synthesis, Study Of 6-((5-Phenethyl-4-R-1,2,4-triazole-3-ylthio)pyridyn-3-yl)-(alkyl, heteryl)methanimines And Their Derivatives. Žurnal organìčnoï ta farmacevtičnoï hìmìï, 16(4 (64)), 34-39.
Shcherbyna, R. O. (2014). Pharmacological Activity Analysis Of The 1,2,4-Triazole Derivatives. Pharmaceutical Journal, (4), 145-150.
Kaplaushenko A. Synthesis, Structure And Biological Activity Of 4-Mono And 4,5-Di-Substituted 1,2,4-Triazoles-3-thione.(Doctoral dissertation, AG Kaplaushenko- Zaporizhzhya, 2012.-387p).
Shcherbyna, R. A., Panasenko, A. I., Knysh, E. G., & Varinsky, B. A. (2014). Synthesis And Physicochemical Properties Of 2-((4-R-3-(morpholinomethylene)-4H-1,2,4-triazol-5-yl)thio)acetic Acids. Aktualʹnì Pitannâ Farmacevtičnoï ì Medičnoï Nauki ta Praktiki, 3 (16), 18-21.
Safonov A.A., O. I. Panasenko, E. G. Knysh, B.O. Varinsky (2014). Synthesis and physicochemical properties of 4-amino-5-(thiophen-2-ylmethyl)-4H-1,2,4-triazole-3-thiol derivatives. Collection of scientific works of the Ukrainian Military Medical Academy. Problems of military health. 42, 381-385.