Skip to main content
SpringerLink
Log in

Facile, capable, atom-economical one-pot multicomponent strategy for the direct regioselective synthesis of novel isoxazolo[5,4-d]pyrimidines

  • Published:
Research on Chemical Intermediates Aims and scope Submit manuscript

Abstract

Facile and efficient NaOH-promoted one-pot regioselective synthesis of 5,7-dimethyl-3-(arylamino)isoxazolo[5,4-d]pyrimidine-4,6(5H,7H)-diones and 5,7-dimethyl-3-(arylamino)-6-thioxo-6,7-dihydroisoxazolo[5,4-d]pyrimidin-4(5H)-ones as pharmaceutically interesting compounds has been developed based on a three-component reaction between aryl isothiocyanates, N,N-dimethylbarbituric acid or N,N-dimethyl-2-thiobarbituric acid, and hydroxylamine hydrochloride in N,N-dimethylformamide (DMF) at room temperature. This new protocol has advantages such as simple operation, regioselectivity, metal-free operation, high atom economy, moderate to high yield, easy work-up procedure, and applicability on the gram scale.

Graphical abstract

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Scheme 1
Scheme 2
Scheme 3
Scheme 4

Similar content being viewed by others

References

  1. C.H. Gill, A.V. Chat, G.Y. Shinde, A.P. Sarkate, S.V. Tiwari, Res. Chem. Intermed. 44, 4029 (2018)

    Article  CAS  Google Scholar 

  2. M.A. Shaikh, M. Farooqui, S. Abed, Res. Chem. Intermed. 44, 5483 (2018)

    Article  CAS  Google Scholar 

  3. M.H. Sayahi, S. Bahadorikhalili, S.J. Saghanezhad, M. Mahdavi, Res. Chem. Intermed. 44, 5241 (2018)

    Article  CAS  Google Scholar 

  4. M. Ghashang, S. Janghorban, S.J. Roudbaraki, Res. Chem. Intermed. 44, 5013 (2018)

    Article  CAS  Google Scholar 

  5. A.V. Chate, R.M. Dongre, M.K. Khaire, G.M. Bondle, J.N. Sangshetti, M. Damale, Res. Chem. Intermed. 44, 6119 (2018)

    Article  CAS  Google Scholar 

  6. S. Kasaboina, R. Bollu, P.M. Gomedhika, V. Ramineni, L. Nagarapu, N. Dumala, P. Grover, J.B. Nanubolu, Tetrahedron Lett. 59, 3015 (2018)

    Article  CAS  Google Scholar 

  7. A. Mohammadinezhad, B. Akhlaghinia, Aust. J. Chem. 71, 32 (2018)

    Article  CAS  Google Scholar 

  8. J.S. Savithri, P. Rajakumar, Aust. J. Chem. 71, 399 (2018)

    Article  CAS  Google Scholar 

  9. B. Xu, J. Su, J. Wang, G.-C. Zhou, Aust. J. Chem. 69, 1646 (2016)

    Google Scholar 

  10. B. Karmakar, Aust. J. Chem. 69, 1117 (2016)

    Article  CAS  Google Scholar 

  11. N. Devi, R. Shankar, V. Singh, J. Heterocycl. Chem. 55, 373 (2018)

    Article  CAS  Google Scholar 

  12. S.-C. Wang, F.-X. Wan, S. Liu, S. Zhang, L. Jiang, J. Chin. Chem. Soc. 65, 445 (2018)

    Article  CAS  Google Scholar 

  13. M. Rimaz, H. Mousavi, M. Behnam, L. Sarvari, B. Khalili, Curr. Chem. Lett. 6, 55 (2017)

    Article  Google Scholar 

  14. M. Rimaz, H. Mousavi, M. Behnam, B. Khalili, Curr. Chem. Lett. 5, 145 (2016)

    Article  Google Scholar 

  15. M. Yousaf, A.F. Zahoor, S. Faiz, S. Javed, M. Irfan, J. Heterocycl. Chem. 55, 2447 (2018)

    Article  CAS  Google Scholar 

  16. S. Balalaie, M. Shamakli, A. Nikbakht, N.S. Alavijeh, F. Rominger, S. Rostamizadeh, H.R. Bijanzadeh, Org. Biomol. Chem. 15, 5737 (2017)

    Article  CAS  PubMed  Google Scholar 

  17. A.O. Chagarovskiy, E.M. Budynina, O.A. Ivanova, V.B. Rybakov, I.V. Trushkov, M.Y. Melnikov, Org. Biomol. Chem. 14, 2905 (2016)

    Article  CAS  PubMed  Google Scholar 

  18. J.-S. Poh, C. García-Ruiz, A. Zúñiga, F. Meroni, D.C. Blakemore, D.L. Browne, S.V. Ley, Org. Biomol. Chem. 14, 5983 (2016)

    Article  CAS  PubMed  Google Scholar 

  19. W. Liu, P. Zhou, C. Chen, Q. Zhang, Z. Zhu, Org. Biomol. Chem. 11, 542 (2013)

    Article  CAS  PubMed  Google Scholar 

  20. D.V. Vorobyeva, N.M. Karimova, I.L. Odinets, G.-V. Röschenthaler, S.N. Osipov, Org. Biomol. Chem. 9, 7335 (2011)

    Article  CAS  PubMed  Google Scholar 

  21. M. Kaur, A. Kaur, B. Singh, B. Singh, J. Heterocycl. Chem. 54, 80 (2017)

    Article  CAS  Google Scholar 

  22. J. Gaddameedi, D.P. Yelda, R.R. Kuchukulla, K. Chavva, S.R. Pillalamarri, S.K. Gautham, G.K. Chityal, N. Banda, J. Heterocycl. Chem. 54, 194 (2017)

    Article  CAS  Google Scholar 

  23. A.P. Chavan, A.B. Pinjari, P.C. Mhaske, J. Heterocycl. Chem. 52, 1911 (2015)

    Article  CAS  Google Scholar 

  24. H. Kiyani, F. Ghorbani, Res. Chem. Intermed. 42, 6831 (2016)

    Article  CAS  Google Scholar 

  25. R.H. Vekariya, K.D. Patel, H.D. Patel, Res. Chem. Intermed. 42, 7559 (2016)

    Article  CAS  Google Scholar 

  26. A. Mouradzadegun, F. Abadast, S. Elahi, N. Askarikia, Res. Chem. Intermed. 42, 3147 (2016)

    Article  CAS  Google Scholar 

  27. S.N. Maddila, S. Maddila, W.E. van Zyl, S.B. Jonnalagadda, Res. Chem. Intermed. 42, 2553 (2016)

    Article  CAS  Google Scholar 

  28. H. Kiyani, F. Ghorbani, Res. Chem. Intermed. 41, 2653 (2015)

    Article  CAS  Google Scholar 

  29. H. Kiyani, H. Kanaani, D. Ajloo, F. Ghorbani, M. Vakili, Res. Chem. Intermed. 41, 7739 (2015)

    Article  CAS  Google Scholar 

  30. S.S. Basha, K. Divya, A. Padmaja, V. Padmavahthi, Res. Chem. Intermed. 41, 10067 (2015)

    Article  CAS  Google Scholar 

  31. G. Roman, Res. Chem. Intermed. 40, 2039 (2014)

    Article  CAS  Google Scholar 

  32. N. Irannejad-Gheshlaghchaei, A. Zare, S.S. Sajadikhah, A. Banaei, Res. Chem. Intermed. 44, 6253 (2018)

    Article  CAS  Google Scholar 

  33. G.N. Pairas, F. Perperopoulou, P.G. Tsoungas, G. Varvounis, ChemMedChem 12, 408 (2017)

    Article  CAS  PubMed  Google Scholar 

  34. A. Oancea, E. Georgescu, F. Georgescu, A. Nicolescu, E.I. Oprita, C. Tudora, L. Vladulescu, M.-C. Vladulescu, F. Oancea, C. Deleanu, Beilstein J. Org. Chem. 13, 659 (2017)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  35. E. Gilberg, D. Stumpfe, J. Bajorath, RSC Adv. 7, 35638 (2017)

    Article  CAS  Google Scholar 

  36. T. Iami, H. Togo, Eur. J. Org. Chem. 29, 1377 (2018)

    Article  CAS  Google Scholar 

  37. S. Xue, J. Liu, C. Wang, Eur. J. Org. Chem. 2450 (2016)

  38. J. Zhu, J. Mo, H.-Z. Lin, Y. Chen, H.-P. Sun, Bioorg. Med. Chem. 26, 3065 (2018)

    Article  CAS  PubMed  Google Scholar 

  39. C. Lei, L. Geng, X. Xu, X. Shao, Z. Li, Bioorg. Med. Chem. Lett. 28, 831 (2018)

    Article  CAS  PubMed  Google Scholar 

  40. S.S. Prasad, S. Baskaran, J. Org. Chem. 83, 1558 (2018)

    Article  CAS  PubMed  Google Scholar 

  41. T. Morita, S. Fukuhara, S. Fuse, H. Nakamura, Org. Lett. 20, 433 (2018)

    Article  CAS  PubMed  Google Scholar 

  42. M. Mo, J. Yang, X.-C. Jiang, Y. Cao, J. Fei, Y. Chen, X. Qi, Y. Chu, L. Zhou, D. Ye, J. Med. Chem. 61, 8241 (2018)

    Article  CAS  PubMed  Google Scholar 

  43. X. Zhou, X. Xu, Z. Shi, K. Liu, H. Gao, W. Li, Org. Biomol. Chem. 14, 5246 (2016)

    Article  CAS  PubMed  Google Scholar 

  44. B.A. Chalyk, I.Y. Kandaurova, K.V. Hrebeniuk, O.V. Manoilenko, I.B. Kulik, R.T. Iminov, V. Kubyshkin, A.V. Tverdokhlebov, O.K. Ablialimov, P.K. Mykhailiuk, RSC Adv. 6, 25713 (2016)

    Article  CAS  Google Scholar 

  45. Y. He, Y.-Y. Xie, Y.-C. Wang, X.-M. Bin, D.-C. Hu, H.-S. Wang, Y.-M. Pan, RSC Adv. 6, 58988 (2016)

    Article  CAS  Google Scholar 

  46. S. Mohammad, R.A. Vishwakarma, S.B. Bharate, RSC Adv. 5, 3470 (2015)

    Article  CAS  Google Scholar 

  47. A. Mishra, B.B. Mishra, V.K. Tiwari, RSC Adv. 5, 41520 (2015)

    Article  CAS  Google Scholar 

  48. S. Nagaraju, N. Satyanarayana, B. Paplal, A.K. Vasu, S. Kanvah, B. Sridhar, P. Sripadi, D. Kashinath, RSC Adv. 5, 94474 (2015)

    Article  CAS  Google Scholar 

  49. M.M. Bassaco, M.P. Fortes, D.F. Back, T.S. Kaufman, C.C. Silveira, RSC Adv. 4, 60785 (2014)

    Article  CAS  Google Scholar 

  50. C. Görgen, T.J.J. Müller, Chem. Heterocycl. Comp. 53, 422 (2017)

    Article  CAS  Google Scholar 

  51. W. Chen, J. Zhang, B. Wang, Z. Zhao, X. Wang, Y. Hu, J. Org. Chem. 80, 2413 (2015)

    Article  CAS  PubMed  Google Scholar 

  52. C.M. Nunes, I. Reva, R. Fausto, J. Org. Chem. 78, 10657 (2013)

    Article  CAS  PubMed  Google Scholar 

  53. I. Triandafillidi, C.G. Kokotos, Org. Lett. 19, 106 (2017)

    Article  CAS  PubMed  Google Scholar 

  54. S. Samai, T. Chanda, H. Ila, M.S. Singh, Eur. J. Org. Chem. 4026 (2013)

  55. A. Atahan, N. Gencer, C. Bilen, E. Yavuz, H. Genc, F. Sonmez, M. Zengin, M. Ceylan, M. Kucukislamoglu, ChemistrySelect 3, 529 (2018)

    Article  CAS  Google Scholar 

  56. V.A. Adhikari, V.V. Badiger, Arch. Pharm. 320, 1124 (1987)

    Article  CAS  Google Scholar 

  57. W.S. Hamama, M.E. Ibrahim, H.H. Zoorob, J. Heterocycl. Chem. 53, 2007 (2016)

    Article  CAS  Google Scholar 

  58. E. Wagner, L. Becan, J. Heterocycl. Chem. 55, 1880 (2018)

    Article  CAS  Google Scholar 

  59. I.A. Shehata, R.A. Glennon, J. Heterocycl. Chem. 24, 1291 (1987)

    Article  CAS  Google Scholar 

  60. Z. Ji, A.A. Ahmed, D.H. Albert, J.J. Bouska, P.F. Bousquet, G.A. Cunha, K.B. Glaser, J. Guo, J. Li, P.A. Marcotte, M.D. Moskey, L.J. Pease, K.D. Stewart, M. Yates, S.K. Davidsen, M.R. Michaelides, Bioorg. Med. Chem. Lett. 16, 4326 (2006)

    Article  CAS  PubMed  Google Scholar 

  61. E. Wagner, L. Becan, E. Nowakowska, Bioorg. Med. Chem. 12, 265 (2004)

    Article  CAS  PubMed  Google Scholar 

  62. J.-J. Guo, Y.-Y. Liu, Y.-Z. Pei, Chin. Chem. Lett. 26, 1283 (2015)

    Article  CAS  Google Scholar 

  63. G.J. Yu, B. Yang, A.S. Verkman, M.J. Kurth, Synlett 7, 1063 (2010)

    Google Scholar 

  64. S. Kokkonda, F.E. Mazouni, K.L. White, J. White, D.M. Shackleford, M.J. Lafuente-Monasterio, P. Rowland, K. Manjalanagara, J.T. Joseph, A. Garcia-Ṕerez, J. Fernandez, F.J. Gamo, D. Waterson, J.N. Burrows, M.J. Palmer, S.A. Charman, P.K. Rathod, M.A. Philips, ACS Omega 3, 9227 (2018)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  65. V.N. Mahire, G.P. Patil, A.B. Deore, P.G. Chavan, H.D. Jirmali, P.P. Mahulikar, Res. Chem. Intermed. 44, 5801 (2018)

    Article  CAS  Google Scholar 

  66. T. Zhang, J. Zhou, Y. Chen, Y. Li, Res. Chem. Intermed. 44, 5329 (2018)

    Article  CAS  Google Scholar 

  67. F. Mousavizadeh, M. Talebizadeh, M. Anary-Abbasinejad, Tetrahedron Lett. 59, 2970 (2018)

    Article  CAS  Google Scholar 

  68. W. Qian, D. Wang, H. Wang, P. Yu, S. Liu, S. Chen, Tetrahedron Lett. 59, 2167 (2018)

    Article  CAS  Google Scholar 

  69. B. Mitra, S. Mukherjee, G.C. Pariyar, P. Ghosh, Tetrahedron Lett. 59, 1385 (2018)

    Article  CAS  Google Scholar 

  70. G. Khanna, P. Saluja, J.M. Khurana, Aust. J. Chem. 70, 1285 (2017)

    Article  CAS  Google Scholar 

  71. V. Ajavakom, T. Yutthaseri, R. Chantanatrakul, A. Suksamran, A. Ajavakom, J. Heterocycl. Chem. 55, 13 (2018)

    Article  CAS  Google Scholar 

  72. S. Gadekar, P.M.K. Lande, Res. Chem. Intermed. 44, 3267 (2018)

    Article  CAS  Google Scholar 

  73. S.F. Hojati, A. Amiri, S. Mohamadi, N. Moeini Eghbali, Res. Chem. Intermed. 44, 2275 (2018)

    Article  CAS  Google Scholar 

  74. N. Azizi, M. Edrisi, Res. Chem. Intermed. 43, 379 (2017)

    Article  CAS  Google Scholar 

  75. C.-W. Lü, J.-J. Wang, F. Li, S.-J. Yu, Y. An, Res. Chem. Intermed. 44, 1035 (2018)

    Article  CAS  Google Scholar 

  76. K.G. Patel, N.M. Misra, R.H. Vekariya, R.R. Shettigar, Res. Chem. Intermed. 44, 289 (2018)

    Article  CAS  Google Scholar 

  77. M. Rimaz, H. Mousavi, P. Keshavarz, B. Khalili, Curr. Chem. Lett. 4, 159 (2015)

    Article  Google Scholar 

  78. M. Ghandi, S. Rahimi, N. Zarezadeh, J. Heterocycl. Chem. 54, 102 (2017)

    Article  CAS  Google Scholar 

  79. J. Safaei-Ghomi, H. Shahbazi-Alavi, S.H. Nazemzadeh, J. Chin. Chem. Soc. 64, 1213 (2017)

    Article  CAS  Google Scholar 

  80. Z.R. Moosavi-Zare, H. Goudarziafshar, S. Dastbaz, J. Chin. Chem. Soc. 64, 727 (2017)

    Article  CAS  Google Scholar 

  81. H. Alinezhad, V. Alinezhad, S. Mohseni Tavakkoli, J. Chin. Chem. Soc. 64, 385 (2017)

    Article  CAS  Google Scholar 

  82. E. Tabrizian, A. Amoozadeh, J. Chin. Chem. Soc. 64, 331 (2017)

    Article  CAS  Google Scholar 

  83. B. Zeynizadeh, R. Younesi, H. Mousavi, Res. Chem. Intermed. 44, 7331 (2018)

    Article  CAS  Google Scholar 

  84. M.K. Mehra, M.P. Tantak, V. Arun, I. Kumar, D. Kumar, Org. Biomol. Chem. 15, 4959 (2017)

    Article  Google Scholar 

  85. G. Ramachandran, N.S. Karthikeyan, P. Giridharan, K.I. Sathiyanarayanan, Org. Biomol. Chem. 10, 5343 (2012)

    Article  CAS  PubMed  Google Scholar 

  86. J.-Y. Liu, H. Zhang, B.-M. Feng, B. Jiang, S.-L. Wang, S.-J. Tu, Org. Biomol. Chem. 10, 8533 (2012)

    Article  CAS  Google Scholar 

  87. H. Ma, C. Guo, Z. Zhan, G. Lu, Y. Zhang, X. Luo, X. Cui, G. Huang, New J. Chem. 41, 5280 (2017)

    Article  CAS  Google Scholar 

  88. S. Ambethkar, M.M. Kalaiselvi, V. Padmini, N. Bhuvanesh, ChemistrySelect 2, 5329 (2017)

    Article  CAS  Google Scholar 

  89. K.-H. Wang, J. Wang, Y. Wang, Y. Su, D. Huang, Y. Fu, Z. Du, Y. Hu, Synthesis 50, 1907 (2018)

    Article  CAS  Google Scholar 

  90. M. Safarzaei, M.T. Maghsoodlou, E. Mollashahi, N. Hazeri, M. Lashkari, Res. Chem. Intermed. 44, 7449 (2018)

    Article  CAS  Google Scholar 

  91. M. Rimaz, H. Mousavi, Turk. J. Chem. 37, 252 (2013)

    CAS  Google Scholar 

  92. M. Rimaz, H. Rabiei, B. Khalili, R.H. Prager, Aust. J. Chem. 67, 283 (2014)

    Article  CAS  Google Scholar 

  93. M. Rimaz, Aust. J. Chem. 68, 1529 (2015)

    Article  CAS  Google Scholar 

  94. M. Rimaz, Z. Jalalian, H. Mousavi, R.H. Prager, Tetrahedron Lett. 57, 105 (2016)

    Article  CAS  Google Scholar 

  95. M. Rimaz, J. Khalafy, H. Mousavi, Res. Chem. Intermed. 42, 8185 (2016)

    Article  CAS  Google Scholar 

  96. M. Rimaz, F. Aali, Chin. J. Catal. 37, 517 (2016)

    Article  CAS  Google Scholar 

  97. M. Rimaz, F. Aali, B. Khalili, R.H. Prager, Aust. J. Chem. 70, 660 (2017)

    Article  CAS  Google Scholar 

  98. M. Rimaz, H. Mousavi, L. Nikpey, B. Khalili, Res. Chem. Intermed. 43, 3925 (2017)

    Article  CAS  Google Scholar 

  99. M. Rimaz, J. Khalafy, H. Mousavi, S. Bohlooli, B. Khalili, J. Heterocycl. Chem. 54, 3174 (2017)

    Article  CAS  Google Scholar 

  100. M. Rimaz, B. Khalili, G. Khatyal, H. Mousavi, F. Aali, Aust. J. Chem. 70, 1274 (2017)

    Article  CAS  Google Scholar 

  101. M. Rimaz, H. Mousavi, B. Khalili, F. Aali, J. Chin. Chem. Soc. 65, 1389 (2018)

    Article  CAS  Google Scholar 

  102. N. Matsumoto, M. Takahashi, Tetrahedron 58, 10073 (2002)

    Article  CAS  Google Scholar 

  103. T.-L. Ho, Chem. Rev. 75, 1 (1975)

    Article  CAS  Google Scholar 

  104. T.-L. Ho, J. Chem. Educ. 55, 335 (1978)

    Article  Google Scholar 

  105. P.K. Chattaraj, H. Lee, R.G. Parr, J. Am. Chem. Soc. 113, 1855 (1991)

    Article  CAS  Google Scholar 

  106. P.K. Chattaraj, P.V.R. Schleyer, J. Am. Chem. Soc. 116, 1067 (1994)

    Article  CAS  Google Scholar 

  107. R.G. Pearson, J. Am. Chem. Soc. 85, 3533 (1963)

    Article  CAS  Google Scholar 

Download references

Acknowledgements

We are grateful for financial support from the Research Council of Payame Noor University.

Author information

Authors and Affiliations

  1. Department of Chemistry, Payame Noor University, PO Box 19395-3697, Tehran, Iran

    Mehdi Rimaz, Hossein Mousavi & Leila Ozzar

  2. Department of Organic Chemistry, Faculty of Chemistry, Urmia University, Urmia, Iran

    Hossein Mousavi

  3. Department of Chemistry, Faculty of Sciences, University of Guilan, PO Box 41335-1914, Rasht, Iran

    Behzad Khalili

Authors
  1. Mehdi Rimaz
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Hossein Mousavi
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Leila Ozzar
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Behzad Khalili
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Mehdi Rimaz.

Ethics declarations

Conflict of interest

The authors declare no conflicts of interest.

Additional information

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOC 29261 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Rimaz, M., Mousavi, H., Ozzar, L. et al. Facile, capable, atom-economical one-pot multicomponent strategy for the direct regioselective synthesis of novel isoxazolo[5,4-d]pyrimidines. Res Chem Intermed 45, 2673–2694 (2019). https://doi.org/10.1007/s11164-019-03757-9

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-019-03757-9

Keywords

Search

Navigation