Catalyst-free synthesis of various derivatives of a novel heterocyclic system of 3-alkyl-9-methyl-tetrazolo[1,5-a][1,2,3]triazolo[4,5-d]pyrimidine

Document Type : Original Article

Authors

Department of Chemistry, Faculty of Science, Ferdowsi University of Mashhad, Mashhad, Iran

Abstract

Azolo-annulated pyrimidines have attracted continuing interest due primarily to their structural similarity to heterocyclic bases of DNA and RNA. As a consequence, these compounds can act as antimetabolites, being effective biologically active compounds. Numerous advantageous properties of azolopyrimidines such as important industrial, agrochemical and pharmaceutical applications, especially in biological science, material chemistry and medicinal chemistry impelled us to design and synthesis of a number of various and interesting derivatives of 3-alkyl-9-methyl-tetrazolo[1,5-a][1,2,3]triazolo[4,5-d]pyrimidine as a novel heterocyclic system which has not been reported previously. In the present work, initially the reaction of 2,4-dichloro-6-methylpyrimidin-5-amine (1) with different primary amines in refluxing i-PrOH gave the corresponding sec-amino derivatives (2a-e) which were consequently treated with NaNO2/HCl solution to yield quantitatively the corresponding diazo derivatives of 5-chloro-3-alkyl-7-methyl-3H-[1,2,3]triazolo[4,5-d]pyrimidine (3a-e). Further reaction of compounds (3a-e) with NaN3 in EtOH was resulted in various derivatives of novel heterocyclic system of tetrazolo[1,5-a][1,2,3]triazolo[4,5-d]pyrimidine (4a-e) that are in equilibrium with azide forms.

Keywords

References

[1] Z. Fallah, H. Nasr Isfahani, M. Tajbakhsh, H. Tashakkorian  and A. Amouei, J. Of Applied Chemistry, 14 (1398) 303, in Persian. (This style is for Persian Journal Papers)
[2] M. Javaherian, F. Kazemi, M. R. Kalantarzadeh and H. Motamedi, J. Of Applied Chemistry, 12 (1396) 9, in Persian.
[3] F. Taghavi and M. Eshaghi, J. Of Applied Chemistry, 15 (1399) 207, in Persian.
[4] S. Kumari, D. Idrees, C. B. Mishra, A. Prakash, F. Ahmad, M. I. Hassan and M. Tiwari, J. Mol. Graph. Model. 64 (2016) 101. (This style is for Journal Papers)
[5] A. O. Abdelhamid, I. E. El Sayed, M. Z. Hussein and M. M. Mangoud, Molecules. 21 (2016) 1072.
[6] J. Kumar, P. Meena, A. Singh, E. Jameel, M. Maqbool, M. Mobashir, A. Shandilya, M. Tiwari, N. Hoda and B. Jayaram, Eur. J. Med. Chem. 119 (2016) 260.
[7] P. Singla, V. Luxami, R. Singh, V. Tandon and K. Paul, Eur. J. Med. Chem. 126 (2017) 24.
[8] S. Husted and J. J. J. Van Giezen, Cardiovasc. Ther. 27 (2009) 259.
[9] V. D. Orlov, S. M. Desenko and N. S. Pivnenko, Chem. Heterocycl. Compd. 24 (1988) 1233.
[10] Z. -H. Li, X. -Q. Liu, P. -F. Geng, F. -Z. Suo, J. -L. Ma, B. Yu, T. -Q. Zhao, Z. -Q. Zhou, C. -X. Huang and Y. -C. Zheng, ACS Med. Chem. Lett. 8 (2017) 384.
[11] P. -F. Geng, X. -Q. Liu, T. -Q. Zhao, C. -C. Wang, Z. -H. Li, J. Zhang, H. -M. Wei, B. Hu, L. -Y. Ma and H. -M. Liu, Eur. J. Med. Chem. 146 (2018) 147.
[12] Z. Li, L. Ding, Z. Li, Z. Wang, F. Suo, D. Shen, T. Zhao, X. Sun, J. Wang and Y. Liu, Acta Pharm. Sin. B. 9 (2019) 794.
[13] C. M. Dehnhardt, A. M. Venkatesan, E. Delos Santos, Z. Chen, O. Santos, S. Ayral-Kaloustian, N. Brooijmans, R. Mallon, I. Hollander and L. Feldberg, J. Med. Chem. 53 (2010) 798.
[14] G. Aromí, L. A. Barrios, O. Roubeau and P. Gamez, Coord. Chem. Rev. 255 (2011) 485.
[15] W. P. Fehlhammer and L. F. Dahl, J. Am. Chem. Soc. 94 (1972) 3370.
[16] J. G. Haasnoot, Coord. Chem. Rev. 200 (2000) 131.
[17] M. Sahu and N. Siddiqui, Int. J. Pharm. Pharm. Sci. 8 (2016) 8.
[18] A. M. Hussein and O. M. Ahmed, Bioorg. Med. Chem. 18 (2010) 2639.
[19] M. Adib, E. Sheibani, H. R. Bijanzadeh and L. -G. Zhu, Tetrahedron 64 (2008) 10681.
[20] A. M. Hussein, J. Saudi Chem. Soc. 14 (2010) 61.
[21] Y. Takayama, Y. Yoshida and M. Uehata "Visual function disorder improving agents" US Patent 7,109,208 (2006).
[22] A. Fujii, H. Tanaka, M. Otsuki, T. Kawaguchi and K. Oshita "Antitumor effect potentiators" U.S. Patent 6,930,115 (2005).
[23] M. J. Jawad, S. M. Hassan, S. W. Ahjel, N. R. Hadi and S. M. Awad, Lat. Am. J. Pharm. 40 (2021) 131.
[24] Y. Li, W. Yao, J. Lin, G. Gao, C. Huang and Y. Wu, Monatshefte Für Chemie-Chemical Mon. 152 (2021) 121.
[25] G. E. Aspnes and Y. -C. P. Chiang "Tetrazole compounds as thyroid receptor ligands" US Patent 6,441,015 (2002).
[26] Q. -A. Sun, D. T. Hess, B. Wang, M. Miyagi and J. S. Stamler, Free Radic. Biol. Med. 52 (2012) 1897.
[27] E. Scapin, C. P. Frizzo, L. V. Rodrigues, G. C. Zimmer, R. A. Vaucher, M. R. Sagrillo, J. L. Giongo, C. A. M. Afonso, P. Rijo and N. Zanatta, Med. Chem. Res. 26 (2017) 640.
[28] A. M. Dougherty, H. Guo, G. Westby, Y. Liu, E. Simsek, J. -T. Guo, A. Mehta, P. Norton, B. Gu and T. Block, Antimicrob. Agents Chemother. 51 (2007) 4427.
[29] E. A. Popova, A. V Protas and R. E. Trifonov, Anti-Cancer Agents Med. Chem. (Formerly Curr. Med. Chem. Agents). 17 (2017) 1856.
[30] V. L. Gein, T. M. Zamaraeva, V. V Mishunin and V. P. Kotegov, Russ. J. Gen. Chem. 86 (2016) 286.
[31] L. -Y. Zeng and C. Cai, J. Comb. Chem. 12 (2010) 35.
[32] C. Yao, S. Lei, C. Wang, C. Yu and S. Tu, J. Heterocycl. Chem. 45 (2008) 1609.
[33] V. L. Gein, I. N. Vladimirov, O. V Fedorova, A. A. Kurbatova, N. V Nosova, I. V Krylova and M. I. Vakhrin, Russ. J. Org. Chem. 46 (2010) 699.
[34] R. Ghorbani-Vaghei, Z. Toghraei-Semiromi, M. Amiri and R. Karimi-Nami, Mol. Divers. 17 (2013) 307.
[35] A. Maleki, M. Niksefat, J. Rahimi and S. Azadegan, Polyhedron. 167 (2019) 103.
[36] N. Shekarlab, R. Ghorbani-Vaghei and S. Alavinia, J. Organomet. Chem. 949 (2021) 121971.
[37] S. Sheikhi-mohammareh, A. Shiri and M. Bakavoli, J. Chem. Res. 39 (2015) 403.
[38] S. Sheikhi-Mohammareh, A. Shiri, M. Bakavoli and J. Mague, J. Heterocycl. Chem. 53 (2016) 1231.
[39] S. Sheikhi-Mohammareh and A. Shiri, J. Heterocycl. Chem. 55 (2018) 2055.
[40] S. Sheikhi‐Mohammareh, A. Shiri, E. H. Maleki, M. M. Matin, H. Beyzaei, P. Baranipour, F. Oroojalian and T. Memariani, ChemistrySelect. 5 (2020) 10060.
[41] S. Sheikhi-Mohammareh, M. Mashreghi and A. Shiri, J. Iran. Chem. Soc. 17 (2020) 1555.
[42] S. Sheikhi-Mohammareh, A. Shiri, H. Beyzaei and E. Yarmohammadi, Monatshefte Für Chemie - Chem. Mon. 151 (2020) 963.
[43] S. Bigonah-Rasti, S. Sheikhi-Mohammareh, K. Saadat and A. Shiri, Polycycl. Aromat. Compd. 0 (2020) 1. https://doi.org/10.1080/10406638.2020.1852287.
[44] S. Sheikhi-Mohammareh, A. Shiri and J. Mague, Mol. Divers. (2021). https://doi.org/10.1007/s11030-021-10203-9.
[45] O. Kohandel, S. Sheikhi-Mohammareh, F. Oroojalian, T. Memariani and J. Mague, Mol. Divers. (2021). https://doi.org/10.1007/s11030-021-10290-8.
[46] A. Gigante, M. -D. Canela, L. Delang, E. -M. Priego, M. -J. Camarasa, G. Querat, J. Neyts, P. Leyssen and M. -J. Pérez-Pérez, J. Med. Chem. 57 (2014) 4000.
[47] S. Mozafari, A. Shiri, M. Bakavoli, M. Akbarzadeh, K. Saadat and
Y. Etemadi,  J. Chem. Res. 40 (2016) 633.
Applied Chemistry
Volume 17, Issue 64
November 2022
Pages 189-204

Files

Share

How to cite

Statistics