Electro-catalyzed multicomponent transformation of 3-methyl-1-phenyl-1H-pyrazol-5(4H)-one to 1,4-dihydropyrano[2,3-c]pyrazole derivatives in green medium

Zahra Vafajoo Nourallah Hazeri Malek Taher Maghsoodlou Hojat Veisi

Citation:  Zahra Vafajoo, Nourallah Hazeri, Malek Taher Maghsoodlou, Hojat Veisi. Electro-catalyzed multicomponent transformation of 3-methyl-1-phenyl-1H-pyrazol-5(4H)-one to 1,4-dihydropyrano[2,3-c]pyrazole derivatives in green medium[J]. Chinese Chemical Letters, 2015, 26(8): 973-976. doi: 10.1016/j.cclet.2015.04.016 shu

Electro-catalyzed multicomponent transformation of 3-methyl-1-phenyl-1H-pyrazol-5(4H)-one to 1,4-dihydropyrano[2,3-c]pyrazole derivatives in green medium

    通讯作者: Zahra Vafajoo,
    Nourallah Hazeri,
摘要: An efficient and convenient synthesis of 1,4-dihydropyrano[2,3-c]pyrazole derivatives is described, using the electrogenerated anion of ethanol as the base in the presence of sodium bromide as an supporting electrolyte in a one-pot, three component condensation of malononitrile, aromatic aldehydes and 3-methyl-1-phenyl-1H-pyrazol-5(4H)-one. The reaction is carried out in an undivided cell containing an iron electrode as the cathode and a graphite electrode as the anode, at a constant current at room temperature.

English

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    1. [1] R.C. Cioc, E. Ruijter, R.V.A. Orru, Multicomponent reactions: advanced tools for sustainable organic synthesis, Green Chem. 16 (2014) 2958-2975.[1] R.C. Cioc, E. Ruijter, R.V.A. Orru, Multicomponent reactions: advanced tools for sustainable organic synthesis, Green Chem. 16 (2014) 2958-2975.

    2. [2] L.A. Wessjohann, R.A.W. Neves Filho, A.R. Puentes, M.C. Morejon, Macrocycles from multicomponent reactions, multicomponent reactions in organic synthesis, vol. 2, Wiley-VCH Verlag GmbH & Co. KGaA, 2015, pp. 231-261.[2] L.A. Wessjohann, R.A.W. Neves Filho, A.R. Puentes, M.C. Morejon, Macrocycles from multicomponent reactions, multicomponent reactions in organic synthesis, vol. 2, Wiley-VCH Verlag GmbH & Co. KGaA, 2015, pp. 231-261.

    3. [3] S. Su, C. Li, X. Jia, J. Li, Isocyanide-based multicomponent reactions: concise synthesis of spirocyclic oxindoles with molecular complexity by using a [1,5]-hydrogen shift as the key step, Chemistry 20 (2014) 5905-5909.[3] S. Su, C. Li, X. Jia, J. Li, Isocyanide-based multicomponent reactions: concise synthesis of spirocyclic oxindoles with molecular complexity by using a [1,5]-hydrogen shift as the key step, Chemistry 20 (2014) 5905-5909.

    4. [4] L.Wang, J. Gao, L.Wan, Y.Wang, C. Yao, Electrocatalytic multicomponent transformation of cyclopentane-1,3-dione, aldehydes andmalononitrile: an efficientway to cyclopenta[b]pyran derivatives, Res. Chem. Intermed. 41 (2015) 2775-2784.[4] L.Wang, J. Gao, L.Wan, Y.Wang, C. Yao, Electrocatalytic multicomponent transformation of cyclopentane-1,3-dione, aldehydes andmalononitrile: an efficientway to cyclopenta[b]pyran derivatives, Res. Chem. Intermed. 41 (2015) 2775-2784.

    5. [5] A. Shaabani, A. Sarvary, A.H. Rezayan, S. Keshipour, Synthesis of fully substituted pyrano[2,3-c]pyrazole derivatives via a multicomponent reaction of isocyanides, Tetrahedron 65 (2009) 3492-3495.[5] A. Shaabani, A. Sarvary, A.H. Rezayan, S. Keshipour, Synthesis of fully substituted pyrano[2,3-c]pyrazole derivatives via a multicomponent reaction of isocyanides, Tetrahedron 65 (2009) 3492-3495.

    6. [6] R.S. Balaskar, S.N. Gavade, M.S. Mane, et al., Greener approach towards the facile synthesis of 1, 4-dihydropyrano [2,3-c] pyrazol-5-yl cyanide derivatives at room temperature, Chin. Chem. Lett. 21 (2010) 1175-1179.[6] R.S. Balaskar, S.N. Gavade, M.S. Mane, et al., Greener approach towards the facile synthesis of 1, 4-dihydropyrano [2,3-c] pyrazol-5-yl cyanide derivatives at room temperature, Chin. Chem. Lett. 21 (2010) 1175-1179.

    7. [7] J. Albadi, A. Mansournezhad, Z. Derakhshandeh, CuO-CeO2 nanocomposite: a highly efficient recyclable catalyst for the multicomponent synthesis of 4Hbenzo[ b]pyran derivatives, Chin. Chem. Lett. 24 (2013) 821-824.[7] J. Albadi, A. Mansournezhad, Z. Derakhshandeh, CuO-CeO2 nanocomposite: a highly efficient recyclable catalyst for the multicomponent synthesis of 4Hbenzo[ b]pyran derivatives, Chin. Chem. Lett. 24 (2013) 821-824.

    8. [8] A. Siddekhab, A. Nizama, M.A. Pasha, An efficient and simple approach for the synthesis of pyranopyrazoles using imidazole (catalytic) in aqueous medium, and the vibrational spectroscopic studies on 6-amino-4-(4'-methoxyphenyl)-5-cyano-3-methyl-1-phenyl-1,4-dihydropyrano[2,3-c]pyrazole using density functional theory, Spectrochim. Acta A 81 (2011) 431-440.[8] A. Siddekhab, A. Nizama, M.A. Pasha, An efficient and simple approach for the synthesis of pyranopyrazoles using imidazole (catalytic) in aqueous medium, and the vibrational spectroscopic studies on 6-amino-4-(4'-methoxyphenyl)-5-cyano-3-methyl-1-phenyl-1,4-dihydropyrano[2,3-c]pyrazole using density functional theory, Spectrochim. Acta A 81 (2011) 431-440.

    9. [9] H.Mecadon, R. Rohman, I. Kharbangar, et al., L-Proline as an efficicent catalyst for the multi-component synthesis of 6-amino-4-alkyl/aryl-3-methyl-2,4-dihydropyrano[2,3-c]pyrazole-5-carbonitriles in water, Tetrahedron Lett. 52 (2011) 3228-3231.[9] H.Mecadon, R. Rohman, I. Kharbangar, et al., L-Proline as an efficicent catalyst for the multi-component synthesis of 6-amino-4-alkyl/aryl-3-methyl-2,4-dihydropyrano[2,3-c]pyrazole-5-carbonitriles in water, Tetrahedron Lett. 52 (2011) 3228-3231.

    10. [10] A. Hasaninejad, M. Shekouhy, N. Golzara, A.K. Zareb, M.M. Doroodmand, Silica bonded n-propyl-4-aza-1-azoniabicyclo[2.2.2]octane chloride (SB-DABCO): A highly efficient, reusable and new heterogeneous catalyst for the synthesis of 4H-benzo[b]pyran derivatives, Appl. Catal. A: Gen. 402 (2011) 11-22.[10] A. Hasaninejad, M. Shekouhy, N. Golzara, A.K. Zareb, M.M. Doroodmand, Silica bonded n-propyl-4-aza-1-azoniabicyclo[2.2.2]octane chloride (SB-DABCO): A highly efficient, reusable and new heterogeneous catalyst for the synthesis of 4H-benzo[b]pyran derivatives, Appl. Catal. A: Gen. 402 (2011) 11-22.

    11. [11] M.M. Heravi, A. Ghodsa, F. Derikvand, K. Bakhtiari, F.F. Bamoharram, H14[NaP5W30O110] catalyzed one-pot three-component synthesis of dihydropyrano[2,3-c]pyrazole and pyrano[2,3-d]pyrimidine derivatives, J. Iran. Chem. Soc. 7 (2010) 615-620.[11] M.M. Heravi, A. Ghodsa, F. Derikvand, K. Bakhtiari, F.F. Bamoharram, H14[NaP5W30O110] catalyzed one-pot three-component synthesis of dihydropyrano[2,3-c]pyrazole and pyrano[2,3-d]pyrimidine derivatives, J. Iran. Chem. Soc. 7 (2010) 615-620.

    12. [12] Z. Vafajoo, H. Veisi, M.T. Maghsoodlou, H. Ahmadian, Electrocatalytic multicomponent assembling of aldehydes, 4-hydroxycoumarin and malononitrile: an efficient approach to 2-amino-5-oxo-4,5-dihydropyrano(3,2-c)chromene-3-carbonitrile derivatives, C. R. Chim. 17 (2014) 301-304.[12] Z. Vafajoo, H. Veisi, M.T. Maghsoodlou, H. Ahmadian, Electrocatalytic multicomponent assembling of aldehydes, 4-hydroxycoumarin and malononitrile: an efficient approach to 2-amino-5-oxo-4,5-dihydropyrano(3,2-c)chromene-3-carbonitrile derivatives, C. R. Chim. 17 (2014) 301-304.

    13. [13] P. Wexler, Encyclopedia of Toxicology, second ed., Elsevier, 2005.[13] P. Wexler, Encyclopedia of Toxicology, second ed., Elsevier, 2005.

    14. [14] M. Greenberg, in: U.S. Environmental Protection Agency, Washington, DC, 1999, pp. 35.[14] M. Greenberg, in: U.S. Environmental Protection Agency, Washington, DC, 1999, pp. 35.

    15. [15] S.R. Mandha, S. Siliveri, M. Alla, V.R. Bommena, M.R. Bommineni, S. Balasubramanian, Eco-friendly synthesis and biological evaluation of substituted pyrano[2,3-c] pyrazoles, Bioorg. Med. Chem. Lett. 22 (2012) 5272-5278.[15] S.R. Mandha, S. Siliveri, M. Alla, V.R. Bommena, M.R. Bommineni, S. Balasubramanian, Eco-friendly synthesis and biological evaluation of substituted pyrano[2,3-c] pyrazoles, Bioorg. Med. Chem. Lett. 22 (2012) 5272-5278.

    16. [16] C.S. Yao, Y. Wang, T.J. Li, et al., A pseudo multi-component electrochemical synthesis of spiro dihydrofuran derivatives, Tetrahedron 69 (2013) 10593-10597.[16] C.S. Yao, Y. Wang, T.J. Li, et al., A pseudo multi-component electrochemical synthesis of spiro dihydrofuran derivatives, Tetrahedron 69 (2013) 10593-10597.

    17. [17] M.N. Elinson, A.I. Ilovaisky, A.S. Dorofeev, et al., Electrocatalytic multicomponent transformation of cyclic 1,3-diketones, isatins, and malononitrile: facile and convenient way to functionalized spirocyclic (5,6,7,8-tetrahydro-4H-chromene)-4,3'-oxindole system, Tetrahedron 63 (2007) 10543-10548.[17] M.N. Elinson, A.I. Ilovaisky, A.S. Dorofeev, et al., Electrocatalytic multicomponent transformation of cyclic 1,3-diketones, isatins, and malononitrile: facile and convenient way to functionalized spirocyclic (5,6,7,8-tetrahydro-4H-chromene)-4,3'-oxindole system, Tetrahedron 63 (2007) 10543-10548.

    18. [18] S. Makarem, A.A. Mohammadi, A.R. Fakhari, A multi-component electro-organic synthesis of 2-amino-4H-chromenes, Tetrahedron Lett. 49 (2008) 7194-7196.[18] S. Makarem, A.A. Mohammadi, A.R. Fakhari, A multi-component electro-organic synthesis of 2-amino-4H-chromenes, Tetrahedron Lett. 49 (2008) 7194-7196.

    19. [19] M.N. Elinson, A.S. Dorofeev, R.F. Nasybullin, G.I. Nikishin, Facile and convenient synthesis of 4,4'-(Arylmethylene)bis(1H-pyrazol-5-ols) by electrocatalytic Tandem Knoevenagel-Michael reaction, Synthesis (2008) 1933-1937.[19] M.N. Elinson, A.S. Dorofeev, R.F. Nasybullin, G.I. Nikishin, Facile and convenient synthesis of 4,4'-(Arylmethylene)bis(1H-pyrazol-5-ols) by electrocatalytic Tandem Knoevenagel-Michael reaction, Synthesis (2008) 1933-1937.

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  • 发布日期:  2015-04-18
  • 收稿日期:  2015-02-01
  • 网络出版日期:  2015-03-19
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