Synthesis And Characterization of Some 1,2,4-Triazole Derivatives

Authors

  • Vikash Singh Department of chemistry, Maharishi Markandeshwar (Deemed to be University) Mullana, Ambala Author
  • Bhawna Pareek Department of chemistry, Maharishi Markandeshwar (Deemed to be University) Mullana, Ambala Author
  • Mayank Kinger Chaudhary Bansi Lal University, Bhiwani Author
  • Sushil Kumar Department of chemistry, Maharishi Markandeshwar (Deemed to be University) Mullana, Ambala Author
  • Vivek Sharma Department of chemistry, Maharishi Markandeshwar (Deemed to be University) Mullana, Ambala Author
  • Satvinder Khatkar Department of chemistry, Maharishi Markandeshwar (Deemed to be University) Mullana, Ambala Author

DOI:

https://doi.org/10.70130/CAST.2022.5207

Keywords:

IBD, H2SO4, DICHLORO BENZENE, HETEROCYCLIC COMPOUNDS

Abstract

In this study on the synthesis of fused 3-(3-aryl-phenyl-1H-pyrazol-4-yl)-[1,2,4]triazolo-benzothiazoles by the oxidation of 2-((3-aryl)-1- phenyl-1H-pyrazol-4-yl)methylene)-1-(benzothiazol-2-yl)hydrazines using IBD in dichloromethane with an exception to find new and more potent bioactive agents. 

Author Biography

  • Mayank Kinger, Chaudhary Bansi Lal University, Bhiwani

    Mayank Kinger currently works at the Chemistry Programme, Chaudhary Bansi Lal University, Bhiwani. Mayank does research in Organic Chemistry, Nanotechnology and Materials Chemistry. Their current project is 'synthetic organic chemistry'. https://www.researchgate.net/profile/Mayank-Kinger Email: mayank.kinger@yahoo.com Mobile: 91-9034359496 Qualifications  Ph.D. (April-2008) Synthetic Organic Chemistry, Kurukshetra University, Kurukshetra, India, Thesis entitled “Synthetic Studies of Nitrogen and Oxygen Containing Heterocyclic Compounds: under the supervision of Prof Om Prakash.  M.Sc. (2002) Organic Chemistry, C. C. S. University, Meerut, India  B.Sc. (2000) S.D. (PG) College Muzaffarnagar, C. C. S. University, Meerut, India

References

Ahmad, I., & Beg, A. Z. (2001). Antimicrobial and phytochemical studies on 45 Indian medicinal plants against multi-drug resistant human pathogens. Journal of Ethnopharmacology, 74(2), 113–123. https://doi.org/10.1016/s0378-8741(00)00335-4

Al-Burtamani, S. K. S., Fatope, M. O., Marwah, R. G., Onifade, A. K., & Al-Saidi, S. H. (2005). Chemical composition, antibacterial and antifungal activities of the essential oil of Haplophyllum tuberculatum from Oman. Journal of Ethnopharmacology, 96(1–2), 107–112. https://doi.org/10.1016/j.jep.2004.08.039

Aneja, K. R., Sharma, C., & Joshi, R. (2010). Fungal infection of the ear: A common problem in the north eastern part of Haryana. International Journal of Pediatric Otorhinolaryngology, 74(6), 604–607. https://doi.org/10.1016/j.ijporl.2010.03.001

Bauer, V. J., Dalalian, H. P., Fanshawe, W. J., Safir, S. R., Tocus, E. C., & Boshart, C. R. (1968). 4-[3 (5)-pyrazolyl] pyridinium salts. A new class of hypoglycemic agents. Journal of Medicinal Chemistry, 11(5), 981–984. https://doi.org/10.1021/jm00311a015

Bebernitz, G. R., Argentieri, G., Battle, B., Brennan, C., Balkan, B., Burkey, B. F., Eckhardt, M., Gao, J., Kapa, P., Strohschein, R. J., Schuster, H. F., Wilson, M., & Xu, D. D. (2001). The effect of 1, 3-diaryl-[1H]-pyrazole-4-acetamides on glucose utilization in ob/ob mice. Journal of Medicinal Chemistry, 44(16), 2601–2611. https://doi.org/10.1021/jm010032c

Bower, J. D., & Doyle, F. P.. "141. (1957). The preparation of fused triazole systems. Journal of the Chemical Society (Resumed), 727–732.

Bushuev, M. B., Krivopalov, V. P., Nikolaenkova, E. B., Pervukhina, N. V., Naumov, D. Y., & Marianna. I. Rakhmanova. "Zinc (II) and cadmium (II) complexes based on 2-(3, 5-dimethyl-1H-pyrazol-1-yl)-6-(4-methoxyphenyl) pyrimidine-4-carboxylic acid: Synthesis, structure and luminescence." Inorganic Chemistry Communications 14, no. 5 (2011): 749-752.

Derry, C. J., Derry, S., McQuay, H. J., & Moore, R. A. (2006). Systematic review of systematic reviews of acupuncture published 1996–2005. Clinical Medicine, 6(4), 381–386. https://doi.org/10.7861/clinmedicine.6-4-381

Dohi, T., Takenaga, N., Nakae, T., Toyoda, Y., Yamasaki, M., Shiro, M., Fujioka, H., Maruyama, A., & Kita, Y. (2013). Asymmetric dearomatizing spirolactonization of naphthols catalyzed by spirobiindane-based chiral hypervalent iodine species. Journal of the American Chemical Society, 135(11), 4558–4566. https://doi.org/10.1021/ja401074u

Gibson, M. S. (1963). Hydrazones—IV. Tetrahedron, 19(11), 1587–1589. https://doi.org/10.1016/S0040-4020(01)99232-4

Hiremath, S. P., Ullagaddi, A., Shivaramayya, K., & Purohit, M. G. (1999). Amino acid derivatives, VI [1]: Synthesis, antiviral, and antimicrobial evaluation of αamino acid esters bearing a 1, 2, 3-triazolo [4, 5-d] pyrimidinedione side chain. Indian Journal of Heterocyclic Chemistry, 3, 145–148.

Huang, H.-Y., Hou, R.-S., Wang, H.-M., & Chen, L.-C. (2006). Direct α-hydroxylation of aryl ketones using a hypervalent iodine(III) sulfonate. Organic Preparations and Procedures International, 38(5), 473–476. https://doi.org/10.1080/00304940609356439

Hwang, L.-C., Tu, C.-H. T., Wang, J.-H., & Lee, G.-H. (2006). Synthesis and Molecular Structure of 6-amino- 3-benzylmercapto-1, 2, 4-triazolo [3, 4-f][1, 2, 4] triazin-8 (7H)-one. Molecules, 11(2), 169–176. https://doi.org/10.3390/11020169

Kameyama, T., Ukai, M., & Nabeshima, T. (1978). Inhibitory effect of difenamizole on morphine-induced Straub tail reaction with special reference to monoaminergic agents. Chemical and Pharmaceutical Bulletin, 26(11), 3265–3270. https://doi.org/10.1248/cpb.26.3265

Kira, M. A., Abdel-Rahman, M. O., & Gadalla, K. Z. (1969). The Vilsmeier-Haack reaction-III cyclization of hydrazones to pyrazoles. Tetrahedron Letters, 10(2), 109–110. https://doi.org/10.1016/S0040-4039(01)88217-4

Kumar, D., Singh, O. V., Prakash, O., & Singh, S. P. (1994). Oxidation of Chromanones and 2-Spirochromanones with [hydroxy (tosyloxy) iodo] benzene in acetonitrile under Reflux as well as ultrasound: A Convenient Route for the Synthesis of chromones, Tetrahydroxanthones, and Their Higher Homologues. Synthetic Communications, 24(18), 2637–2644. https://doi.org/10.1080/00397919408010576

Kumar, R., Nair, R. R., Dhiman, S. S., Sharma, J., & Prakash, O. (2009). Organoiodine (III)-mediated synthesis of 3-aryl/heteroaryl-5,7-dimethyl-1,2, 4-triazolo [4, 3-c] pyrimidines as antibacterial agents. European Journal of Medicinal Chemistry, 44(5), 2260–2264. https://doi.org/10.1016/j.ejmech.2008.06.004

Manian, R. D. R. S., Jayashankaran, J., Ramesh, R., & Raghunathan, R. (2006). Rapid synthesis of tetrahydroquinolines by indium trichloride catalyzed mono- and bis-intramolecular imino Diels–Alder reactions. Tetrahedron Letters, 47(43), 7571–7574. https://doi.org/10.1016/j.tetlet.2006.08.088

Moriarty, R. M., Vaid, R. K., & Koser, G. F. (1990). [Hydroxy(organosulfonyloxy)iodo]arenes in Organic Synthesis. Synlett, 1990(7), 365–383. https://doi.org/10.1055/s-1990-21097

Okeke, M. I., Iroegbu, C. U., Eze, E. N., Okoli, A. S., & Esimone, C. O. (2001). Evaluation of extracts of the root of Landolphia owerrience for antibacterial activity. Journal of Ethnopharmacology, 78(2–3), 119–127. https://doi.org/10.1016/s0378-8741(01)00307-5

Okimoto, M., & Chiba, T. (1990). Electrochemical oxidation of ketone acylhydrazones and their hydrogen cyanide adducts in sodium cyanide-methanol. Transformation of ketones to nitriles. The Journal of Organic Chemistry, 55(3), 1070–1076. https://doi.org/10.1021/jo00290a048

Papadopoulou, M. V., Bloomer, W. D., Rosenzweig, H. S., Ashworth, R., Wilkinson, S. R., Kaiser, M., Andriani, G., & Rodriguez, A. (2013). 3-nitro-1 H-1, 2, 4-triazole-based compounds as potential anti-chagasic drugs: In vivo studies. Future Medicinal Chemistry, 5(15), 1763–1776. https://doi.org/10.4155/fmc.13.108

Parmar, S. S., Gupta, A. K., Singh, H. H., & Gupta, T. K. (1972). Benzimidazolyl-1, 2, 4-(H)-triazoles as central nervous system depressants. Journal of Medicinal Chemistry, 15(9), 999–1000. https://doi.org/10.1021/jm00279a033

Pollak, A., & Tišler, M. (1966). Synthesis of pyridazine derivatives—V. Tetrahedron, 22(7), 2073–2079. https://doi.org/10.1016/S0040-4020(01)82127-X

Poppe, S. M., Swaney, S. M., Tarpley, W. G., Yagi, Y., Swaney, S. M., Tarpley, W. G., Yagi, Y., Romero, D. L., . . . Romero, D. L." Romero DL. J. (2000). Novel 1,5-diphenylpyrazole nonnucleoside HIV-1 reverse transcriptase inhibitors with enhanced activity versus the delavirdine-resistant P236L mutant: Lead identification and SAR of 3- and 4-substituted derivatives. Journal of Medicinal Chemistry, 43(5), 1034–1040. https://doi.org/10.1021/jm990383f

Prakash, O., Aneja, D. K., Hussain, K., Lohan, P., Ranjan, P., Arora, S., Sharma, C., & Aneja, K. R. (2011). Synthesis and biological evaluation of dihydroindeno and indeno [1, 2-e][1, 2, 4] triazolo [3, 4-b][1, 3, 4] thiadiazines as antimicrobial agents. European Journal of Medicinal Chemistry, 46(10), 5065–5073. https://doi.org/10.1016/j.ejmech.2011.08.019

Prakash, O., Bhardwaj, V., Kumar, R., Tyagi, P., & Aneja, K. R. (2004). Organoiodine (III) mediated synthesis of 3-aryl/hetryl-5, 7-dimethyl-1, 2, 4-triazolo [4, 3-a] pyrimidines as antibacterial agents. European Journal of Medicinal Chemistry, 39(12), 1073–1077. https://doi.org/10.1016/j.ejmech.2004.06.011

Prakash, O., Hussain, K., Aneja, D. K., Sharma, C., & Aneja, K. R. (2011). A facile iodine (III)-mediated synthesis of 3-(3-aryl-1-phenyl-1 H-pyrazol-4-yl)-[1, 2, 4] triazolo [4, 3-a] pyridines via oxidation of 2-((3-aryl-1-phenyl-1 H-pyrazol-4-yl) methylene)-1-(pyridin-2-yl) hydrazines and their antimicrobial evaluations. Organic and Medicinal Chemistry Letters, 1(1), 1. https://doi.org/10.1186/2191-2858-1-1

Prakash, O., Kumar, R., Kumar, R., & Kuhad, R. C. (2007). Organoiodine (III) mediated synthesis of 3, 9-diaryl-and 3, 9- difuryl-bis-1, 2, 4-triazolo [4, 3-a][4, 3-c] pyrimidines as antibacterial agents. European Journal of Medicinal Chemistry, 42(6), 868–872.

Prakash, O., Kumar, R., Sharma, D., Naithani, R., & Kumar, R. (2006). Organoiodine (III)‐mediated efficient synthesis of new 3, 9‐diaryl‐bis‐1, 2, 4‐triazolo [4, 3‐a][4, 3‐c] pyrimidines. Heteroatom Chemistry, 17(7), 653–655. https://doi.org/10.1002/hc.20250

Prakash, O., Sharma, V., Batra, H., & Moriarty, R. M. (2001). (Dichloroiodo)benzene and lead(II) thiocyanate as an efficient reagent combination for stereoselective 1,2-dithiocyanation of alkynes. Tetrahedron Letters, 42(4), 553–555. https://doi.org/10.1016/S0040-4039(00)01909-2

Rečnik, S., Meden, A., Stanovnik, B., & Svete, J. (2008). Ring contractions of 3-Azido-4H-quinolizin-4-ones and 3-azido-4H-azino [1, 2-x] pyrimidin-4-ones: A novel approach to 3-aminoindolizines and their aza analogues. Australian Journal of Chemistry, 61(2), 107–114. https://doi.org/10.1071/CH07318

Sadana, A. K., Mirza, Y., Aneja, K. R., & Prakash, O. M. (2003). Hypervalent iodine mediated synthesis of 1-aryl/hetryl- 1, 2, 4-triazolo [4, 3-a] pyridines and 1-aryl/hetryl 5-methyl-1, 2, 4-triazolo [4, 3-a] quinolines as antibacterial agents. European Journal of Medicinal Chemistry, 38(5), 533–536. https://doi.org/10.1016/s0223-5234(03)00061-8

Varvoglis, A. (1997). Chemical transformations induced by hypervalent iodine reagents. Tetrahedron, 53(4), 1179–1255. https://doi.org/10.1016/S0040-4020(96)00970-2

Zhdankin, V. V. (2009). Hypervalent iodine (III) reagents in organic synthesis. Arkivoc, 2009(1), 1–62. https://doi.org/10.3998/ark.5550190.0010.101

Zhdankin, V. V., & Stang, P. J. (2002). Recent developments in the chemistry of polyvalent iodine compounds. Chemical Reviews, 102(7), 2523–2584. https://doi.org/10.1021/cr010003+

Published

2025-06-14

Issue

Section

Reviews

How to Cite

Singh, V., Pareek, B., Kinger, M., Kumar, S., Sharma, V., & Khatkar, S. (2025). Synthesis And Characterization of Some 1,2,4-Triazole Derivatives. Contemporary Advances in Science and Technology, 5(2), 97-104. https://doi.org/10.70130/CAST.2022.5207

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