An environmentally-friendly base organocatalyzed one-pot strategy for the regioselective synthesis of novel 3,6-diaryl-4-methylpyridazines

doi:10.1016/S1872-2067(15)61060-9

Chinese Journal of Catalysis ›› 2016, Vol. 37 ›› Issue (4): 517-525.DOI: 10.1016/S1872-2067(15)61060-9

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An environmentally-friendly base organocatalyzed one-pot strategy for the regioselective synthesis of novel 3,6-diaryl-4-methylpyridazines

Mehdi Rimaz, Farkhondeh Aali

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

Received:2016-01-07 Revised:2016-01-29 Online:2016-03-30 Published:2016-03-30
Contact: Mehdi Rimaz

Abstract

Abstract:

This report describes a new three-component strategy for the regioselective synthesis of a series of tri-substituted pyridazines via a 1,4-diazabicyclo[2.2.2]octane (DABCO)-catalyzed condensation of propiophenones, arylglyoxalmonohydrates and hydrazine hydrate in water. This method provides a green and convenient one-pot route toward a diverse set of 3,6-diaryl-4-methylpyridazines bearing various aryl substituents. This procedure is highly regioselective, operationally simple, uses water as a safe, environmentally friendly solvent, and DABCO as a green base-organocatalyst, and affords good to excellent yields of products.

Key words: 1,4-Diazabicyclo[2.2.2]octane (DABCO), Propiophenone, Arylglyoxalmonohydrate, Pyridazine

Mehdi Rimaz, Farkhondeh Aali. An environmentally-friendly base organocatalyzed one-pot strategy for the regioselective synthesis of novel 3,6-diaryl-4-methylpyridazines[J]. Chinese Journal of Catalysis, 2016, 37(4): 517-525.

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References

[1] G. P. Ellis, in: Synthesis of Fused Heterocycles, John Wiley and Sons Inc., New York, 1987, 226-239.
[2] T. J. Ritchie, S. J. F. Macdonald, S. Peace, S. D. Pickett, C. N. Luscombe, MedChemComm, 2012, 3, 1062-1069.
[3] C. G. Wermuth, MedChemComm, 2011, 2, 935-941.
[4] D. L. Boger, Chem. Rev., 1986, 86, 781-794.
[5] D. L. Boger, M. Patel, Prog. Heterocycl. Chem., 1989, 1, 30-64.
[6] J. Sauer, in: A. R. Katritzky, C. W. Rees, E. F. V. Scriven eds., Comprehensive Heterocyclic Chemistry II: A Review of the Literature 1982-1995, Pergamon, London, 1996, Vol. 6, 901-955.
[7] J. J. Bourguignon, S. Oumouch, M. Schmitt, Curr. Org. Chem., 2006, 10, 277-295.
[8] C. G. Wermuth, G. Schlewer, J. J. Bourguignon, G. Maghioros, M. J. Bouchet, C. Moire, J. P. Kan, P. Worms, K. Biziere, J. Med. Chem., 1989, 32, 528-537.
[9] A. Volonterio, L. Moisan, J. Rebek Jr., Org. Lett., 2007, 9, 3733-3736.
[10] E. Isabel, D. A. Powell, W. C. Black, C. C. Chan, S. Crane, R. Gordon, J. Guay, S. Guiral, Z. Huang, J. Robichaud, K. Skorey, P. Tawa, L. J. Xu, L. Zhang, R. Oballa, Bioorg. Med. Chem. Lett., 2011, 21, 479-483.
[11] Z. H. Wan, A. Hall, Y. Jin, J. N. Xiang, E. Yang, A. Eatherton, B. Smith, G. Yang, H. H. Yu, J. Wang, L. Ye, L. F. Lau, T. Yang, W. Mitchell, W. Cai, X. M. Zhang, Y. X. Sang, Y. H. Wang, Z. L. Tong, Z. Q. Cheng, I. Hussain, J. D. Elliott, Y. Matsuoka, Bioorg. Med. Chem. Lett., 2011, 21, 4016-4019.
[12] R. J. Gleave, P. J. Beswick, A. J. Brown, G. M. P. Giblin, P. Goldsmith, C. P. Haslam, W. L. Mitchell, N. H. Nicholson, L. W. Page, S. Patel, S. Roomans, B. P. Slingsby, M. E. Swarbrick, Bioorg. Med. Chem. Lett., 2010, 20, 465-468.
[13] T. Asano, H. Yamazaki, C. Kasahara, H. Kubota, T. Kontani, Y. Harayama, K. Ohno, H. Mizuhara, M. Yokomoto, K. Misumi, T. Kinoshita, M. Ohta, M. Takeuchi, J. Med. Chem., 2012, 55, 7772-7785.
[14] J. Sapi, J. Y. Laronze, Arkivoc, 2004, (vii), 208-222.
[15] J. P. Zhu, H. Bienayme, Multicomponent Reactions, Wiley-VCH, Weinheim, 2005.
[16] N. Hazeri, M. T. Maghsoodlou, S. M. Habibi-Khorassani, M. Ziyaadini, G. Marandi, K. Khandan-Barani, H. R. Bijanzadeh, Arkivoc, 2007, (xiii), 34-40.
[17] A. Dömling, B. Beck, E. Herdtweck, W. Antuch, C. Oefner, N. Yehia, A. Gracia-Marques, Arkivoc, 2007, (xii), 99-109.
[18] D. J. Ramon, M. Yus, Angew. Chem. Int. Ed., 2005, 44, 1602-1634.
[19] A. Basso, L. Banfi, R. Riva, G. Guanti, J. Org. Chem., 2005, 70, 575-579.
[20] L. Chen, Y. Du, X. P. Zeng, T. D. Shi, F. Zhou, J. Zhou, Org. Lett., 2015, 17, 1557-1560.
[21] L. Chen, T. D. Shi, J. Zhou, Chem. Asian J., 2013, 8, 556-559.
[22] M. Tisler, R. Stanovnik, Adv. Heterocycl. Chem., 1968, 9, 211-320.
[23] M. D. Bezoari, W. W. Paudler, J. Org. Chem., 1980, 45, 4584-4586.
[24] C. G. Wermuth, G. Schlewer, J. J. Bourguignon, G. Maghioros, M. J. Bouchet, C. Moire, J. P. Kan, P. Worms, K. Biziere, J. Med. Chem., 1989, 32, 528-537.
[25] M. Rimaz, J. Khalafy, Arkivoc, 2010, (ii), 110-117.
[26] M. Rimaz, Z. Jalalian, H. Mousavi, R. H. Prager, Tetrahedron Lett., 2016, 57, 105-109.
[27] M. Rimaz, Aust. J. Chem., 2015, 68, 1529-1534.
[28] M. Rimaz, P. Pourhossein, B. Khalili, Turk. J. Chem., 2015, 39, 244-254.
[29] M. Rimaz, H. Rabiei, B. Khalili, R. H. Prager, Aust. J. Chem., 2014, 67, 283-288.
[30] M. Rimaz, A. Mishokraie, B. Khalili, P. Motiee, Arkivoc, 2015, (v), 88-98.

An environmentally-friendly base organocatalyzed one-pot strategy for the regioselective synthesis of novel 3,6-diaryl-4-methylpyridazines

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