Novel Synthesis of (R)-Imidazolo[1,2c][1,2,3]triazolo[4,5e]pyrimidines

S. Shashidhar Reddy; B. George Vineel; S. Venkataiah; A. Naidu; P.K. Dubey

doi:10.14233/ajchem.2014.17606

Issue

Vol. 26 No. 22 (2014): Vol 26 Issue 22

Issue Published : November 6, 2014

This work is licensed under a Creative Commons Attribution 4.0 International License.

Novel Synthesis of (R)-Imidazolo[1,2c][1,2,3]triazolo[4,5e]pyrimidines

https://doi.org/10.14233/ajchem.2014.17606

S. Shashidhar Reddy

Civenti Chem (India) Private Limited, Plot No-72/A, Part-2, Phase-1, IDA Jeedimetla, Hyderabad-500 055, India

B. George Vineel

Civenti Chem (India) Private Limited, Plot No-72/A, Part-2, Phase-1, IDA Jeedimetla, Hyderabad-500 055, India

S. Venkataiah

Civenti Chem (India) Private Limited, Plot No-72/A, Part-2, Phase-1, IDA Jeedimetla, Hyderabad-500 055, India

A. Naidu

Department of Chemistry, Jawaharlal Nehru Technological University, Kukatpally, Hyderabad-500 085, India

P.K. Dubey

Department of Chemistry, Jawaharlal Nehru Technological University, Kukatpally, Hyderabad-500 085, India

Corresponding Author(s) : S. Shashidhar Reddy

shagum09@gmail.com

Asian Journal of Chemistry, Vol. 26 No. 22 (2014): Vol 26 Issue 22
Article Published : November 6, 2014

Abstract

Commercially available cyanoacetamide (1) was reacted with isopropylazide (2) in the presence of sodium ethoxide in ethanol at 80 °C for 36 h yielding 4-amino-3-isopropyl-3H-[1,2,3]triazolo-5-carboxamide (3) which on treatment with carbon disulphide and potassium hydroxide in ethanol-water under refluxing conditions at 80 °C for 48 h gave 3-isopropyl-5-mercapto-3H-[1,2,3] triazolo[4,5-d]pyrimidine-7-ol (4). The latter on treatment with methyl iodide in aqueous sodium hydroxide at 0 °C for 2 h resulted in 3-isopropyl-5-methanesulfanyl-3H-[1,2,3]triazolo[4,5-d]pyrimidine-7-ol (5). This was reacted with meta-chloroperbenzoic acid (m-CPBA) in dichloromethane at 0 °C for 6 h yielding 3-isopropyl-5-methanesulfonyl-3H-[1,2,3]triazolo[4,5-d]pyrimidine-7-ol (6). Compound 6 was reacted with SOCl₂ in the presence of triethylamine at 75 °C for 6 h to obtain 7-chloro-3-isopropyl-5-methanesulfonyl-3H-[1,2,3]triazolo[4,5-d]pyrimidine (7) which on condensation with D-prolinol (8) in ethanol at room temperature for 2 h resulted in (R)-[1-(5-methanesulfonyl-3-isopropyl-3H-[1,2,3]triazolo[4,5-d]pyrimidine-7-yl)pyrrolidine-2-yl-methanol (9). Compound 9 on treatment with anilines (10a-10g) in microwave oven at 130 °C just for 60 s gave (R)-[1-(5-arylamino-3-isopropyl-3H-[1,2,3]triazolo[4,5-d]pyrimidine-7-yl)pyrrolidine-2yl-methanol (11a-g). The latter, on treatment with polyphosphoric acid at 125 °C for 0.5 h, afforded a series of novel, chiral (R)-N-(3-isopropyl-7a,8,9,10[1'2':3,4]imidazolo [1,2c] [1,2,3]triazolo-[4,5-e]-pyrimidine-5- (7H)ylidine) aniline derivatives (12a-g).

Keywords

Cyanoacetamide Isopropylazide meta-Chloroperbenzoic acid D-Prolinol Triazole Triazolopyrimidine

Shashidhar Reddy, S., George Vineel, B., Venkataiah, S., Naidu, A., & Dubey, P. (2014). Novel Synthesis of (R)-Imidazolo[1,2c][1,2,3]triazolo[4,5e]pyrimidines. Asian Journal of Chemistry, 26(22), 7693–7696. https://doi.org/10.14233/ajchem.2014.17606

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References

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References

L. Havlicek, K. Fuksova, V. Krystof, M. Orsag, B. Vojtesek and M. Strnad, Bioorg. Med. Chem., 13, 5399 (2005); doi:10.1016/j.bmc.2005.06.007.

S.-Y. Chou, W.-K. Yin, Y.-S. Chung, L.-S. Chang, C.-W. Liu, S.-F. Chen and K.-S. Shih, Org. Process Res. Dev., 6, 273 (2002); doi:10.1021/op0100807.

P. Liu, S. Zhu, P. Li, W. Xie, Y. Jin, Q. Sun, Q. Wu, P. Sun, Y. Zhang, X. Yang, Y. Jiang and D. Zhang, Bioorg. Med. Chem. Lett., 18, 3261 (2008); doi:10.1016/j.bmcl.2008.04.056.

B.G. Mohamed, A.A. Abdel-Alim and M.A. Hussein, Acta Pharm., 56, 31 (2006).

A.K. Jordao, P.P. Afonso, Ferreira, M.C. De Souza, M.C. Almeida, C.C. Beltrame, D.P. Paiva, S.M. Wardell, J.L. Wardell, E.R. Tiekink, C.R. Damaso and A.C. Cunha, Eur. J. Med. Chem., 44, 3777 (2009); doi:10.1016/j.ejmech.2009.04.046.

N. Mishra, P. Arora, B. Kumar, L.C. Mishra, A. Bhattacharya, S.K. Awasthi and V.K. Bhasin, Eur. J. Med. Chem., 43, 1530 (2008); doi:10.1016/j.ejmech.2007.09.014.

W.Q. Fan and A.R. Katritzky, in eds.: A.R. Katritzky, C.W. Rees and E.F.V. Scriven, Comprehensive Heterocyclic Chemistry II, Elsevier Science, Oxford, Vol. 4, pp. 1-126 (1996).

N. Zhang, S. Ayral-Kaloustian, T. Nguyen, J. Afragola, R. Hernandez, J. Lucas, J. Gibbons and C. Beyer, J. Med. Chem., 50, 319 (2007); doi:10.1021/jm060717i.

O. Prakash, R. Kumar, R. Kumar, P. tyagi and R.C. Kuhad, Eur. J. Med. Chem., 42, 868 (2007); doi:10.1016/j.ejmech.2006.11.019.

A.M. Kamel and B. Munson, J. Am. Soc. Mass Spectrom., 18, 1477 (2007); doi:10.1016/j.jasms.2007.05.001.

S.M. Sondhi, S. Jain, M. Dinodia, R. Shukla and R. Raghubir, Bioorg. Med. Chem., 15, 3334 (2007); doi:10.1016/j.bmc.2007.03.028.

R.J. Chorvat, R. Bakthavatchalam, J.P. Beck, P.J. Gilligan, R.G. Wilde, A.J. Cocuzza, F.W. Hobbs, R.S. Cheeseman, M. Curry, J.P. Rescinito, P. Krenitsky, D. Chidester, J.A. Yarem, J.D. Klaczkiewicz, C.N. Hodge, P.E. Aldrich, Z.R. Wasserman, C.H. Fernandez, R. Zaczek, L.W. Fitzgerald, S.-M. Huang, H.L. Shen, Y.N. Wong, B.M. Chien, C.Y. Quon and A. Arvanitis, J. Med. Chem., 42, 833 (1999); doi:10.1021/jm980224g.

T. Kumagai, T. Okubo, H. Okubo, S. Chaki, S. Okuyama and A. Nakazato, Bioorg. Med. Chem., 9, 1357 (2001); doi:10.1016/S0968-0896(01)00005-0.

H.A. DeWald, N.W. Beeson, F.M. Hershenson, L.D. Wise, D.A. Downs, T.G. Heffner, L.L. Coughenour and T.A. Pugsley, J. Med. Chem., 31, 454 (1988); doi:10.1021/jm00397a032.

G. Biagi, A.M. Bianucci, A. Coi, B. Costa, L. Fabbrini, I. Giorgi, O. Livi, I. Micco, F. Pacchini, E. Santini, M. Leonardi, F.A. Nofal, O.L.R. Salerni and V. Scartoni, Bioorg. Med. Chem., 13, 4679 (2005); doi:10.1016/j.bmc.2005.04.063.

A. Escher, C. H.L, Kennard, R.J. Quinn and G. Smith, Tetrahedron Lett., 32, 3583 (1991); doi:10.1016/0040-4039(91)80840-3.

A.D. Khoje, A. Kulendrn, C. Charnock, B. Wan, S. Franzblau and L.-L. Gundersen, Bioorg. Med. Chem., 18, 7274 (2010); doi:10.1016/j.bmc.2010.08.016.

R. Alvarez, S. Velazquez, A. San-Felix, S. Aquaro, E. De Clercq, C.-F. Perno, A. Karlsson, J. Balzarini and M.J. Camarasa, J. Med. Chem., 37, 4185 (1994); doi:10.1021/jm00050a015.

S. Velázquez, R. Alvarez, C. Pérez, F. Gago, E. De Clercq, J. Balzarini, M. J. Camarasa, Antivirus Chem. Chemother., 9, 481 (1998).

M. Klein, K. Krainz, I.N. Redwan, P. Dinér and M. Grotli, Molecules, 14, 5124 (2009); doi:10.3390/molecules14125124.

Issue

Vol. 26 No. 22 (2014): Vol 26 Issue 22

Novel Synthesis of (R)-Imidazolo[1,2c][1,2,3]triazolo[4,5e]pyrimidines

Corresponding Author(s) : S. Shashidhar Reddy

Abstract

Keywords

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