Citation: Chen Bo, Liu Weishun, Zhang Jianfang, Liu Jiayi, Deng Guisheng. Synthesis of 3-Phosphonyl Pyrano[3, 2-c]pyrazol-7(1H)-one[J]. Chinese Journal of Organic Chemistry, ;2018, 38(4): 975-980. doi: 10.6023/cjoc201710030 shu

Synthesis of 3-Phosphonyl Pyrano[3, 2-c]pyrazol-7(1H)-one

  • Corresponding author: Deng Guisheng, gsdeng@hunnu.edu.cn
  • Received Date: 24 October 2017
    Revised Date: 26 November 2017
    Available Online: 5 April 2017

    Fund Project: the Hunan Provincial Natural Science Foundation of China 2016JJ2080the National Natural Science Foundation of China 21372071Project supported by the National Natural Science Foundation of China (No. 21372071) and the Hunan Provincial Natural Science Foundation of China (No. 2016JJ2080)

Figures(4)

  • Base-mediated cyclization of 1-diazo-2, 4-dioxo-5-ynylphosphonate provided novel 3-phosphonyl pyrano[3, 2-c] pyrazol-7(1H)-one derivatives in 48%~99% yields. Mild conditions, simple manipulation and functional group diversity are the salient features of this methodology.
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    1. [1]

      For pyrazole see: (a) Harit, T. ; Bellaouchi, R. ; Mokhtari, C. ; Bali, B. E. ; Asehraou, A. ; Malek, F. Tetrahedron 2017, 73, 5138.
      (b) Linda, G. E. ; Moub, T. -C. ; Tamborinid, L. ; Pompere, M. G. ; Michelid, C. D. ; Contid, P. ; Pintof, A. ; Hansena, K. B. Proc. Natl. Acad. Sci. U. S. A. 2017, 114, E6942.
      (c) Zhang, X. -X. ; Jin, H. ; Deng, Y. -J. ; Gao, X. -H. ; Li, Y. ; Zhao, Y. -T. ; Tao, K. ; Hou, T. -P. Chin. Chem. Lett. 2017, 28, 1731. For pyrone see:
      (d) Koyama, T. ; Kawazoe, Y. ; Iwasaki, A. ; Ohno, O. ; Suenaga, K. ; Uemura, D. J. Antibiot. 2016, 69, SI: 348.
      (e) Bertin, M. J. ; Demirkiran, O. ; Navarro, G. ; Moss, N. A. ; Lee, J. ; Goldgof, G. ; Vigil, M. E. ; Winzeler, E. A. ; Valeriote, F. A. ; Gerwick, W. H. Phytochemistry 2016, 122, 113.

    2. [2]

      For pyrazole see: (a) Park, B. -J. ; El-Gamal, M. I. ; Lee, W. -S. ; Shin, J. -S. ; Yoo, K. H. ; Lee, K. -T. ; Oh, C. -H. Med. Chem. Res. 2017, 26, 2161. For γ-pyrone see:
      (b) Obydennov, D. L. ; Khammatova, L. R. ; Sosnovskikh, V. Y. Mendeleev Commun. 2017, 27, 172.
      (c) Ghasemi, Z. ; Mejarshin, F. P. ; Fathi, Z. ; Shahrisa, A. Monatsh. Chem. 2016, 147, 1107.

    3. [3]

      (a) Puerta, D. T. ; Mongan, J. ; Tran, B. L. ; McCammon, J. A. ; Cohen, S. M. J. Am. Chem. Soc. 2005, 127, 14148.
      (b) Pinto, M. M. M. ; Sousa, M. E. ; Nascimento, M. S. J. Curr. Med. Chem. 2005, 12, 2517.
      (c) Morisaki, K. ; Ozaki, S. Chem. Pharm. Bull. 1996, 44, 1647.
      (d) Garey, D. M. ; Ramirez, L. ; Gonzales, S. ; Wertsching, A. ; Tith, S. ; Keefe, K. ; Pena, M. R. J. Org. Chem. 1996, 61, 4853.
      (e) Pantsar, T. ; Singha, P. ; Nevalainen, T. J. ; Koshevoy, I. ; Leppä nen, J. ; Poso, A. ; Niskanen, J. M. A. ; Pasonen-Seppä nen, S. ; Savinainen, J. R. ; Laitinen, T. ; Laitinen, J. T. Eur. J. Pharm. Sci. 2017, 107, 97.

    4. [4]

      Üçüncü, M.; Cantürk, C.; Karakuş, E.; Zeybek, H.; Bozkay, U.; Soydaş, E.; Şahin, E.; Emrullahoğlu, M. Org. Biomol. Chem. 2016, 14, 7490.  doi: 10.1039/C6OB01099G

    5. [5]

      Gelin, S.; Changtegrel, B.; Nadi, A. I. J. Org. Chem. 1983, 48, 4078.  doi: 10.1021/jo00170a041

    6. [6]

      (a) Venkatesham, A. ; Rao, R. S. ; Nagaiah, K. ; Yadav, J. S. ; RoopaJones, G. ; Basha, S. J. ; Sridhard, B. ; Addlagatta, A. Med. Chem. Commun. 2012, 3, 652.
      (b) Gorja, D. R. ; Batchu, V. R. ; Ettam, A. ; Pal, B. M. J. Org. Chem. 2009, 5, 64.
      (c) Kaur, R. ; Taheam, N. ; Sharma, A. K. ; Kharb, R. Res. J. Pharm., Biol. Chem. Sci. 2013, 4, 79.
      (d) Lu, S. ; Tian, J. ; Sun, W. ; Meng, J. ; Wang, X. ; Fu, X. ; Wang, A. ; Lai, D. ; Liu, Y. ; Zhou, L. Molecules 2014, 19, 7169.

    7. [7]

      Deng, G.; Wang, F.; Lu, S.; Cheng, B. Org. Lett. 2015, 17, 4651.  doi: 10.1021/acs.orglett.5b02369

    8. [8]

      (a) Lange, R. ; Heine, R. ; Knapp, R. ; de Klerk, J. M. H. ; Bloemendal, H. J. ; Hendrikse, N. H. Bone 2016, 91, 159.
      (b) Zhao, D. ; Wang, R. Chem. Soc. Rev. 2012, 41, 2095.
      (c) Pradere, U. ; Garnier-Amblard, E. C. ; Coats, S. J. ; Amblard, F. ; R. Schinazi, F. Chem. Rev. 2014, 114, 9154.
      (d) Lange, R. ; ter Heine, R. ; Knapp, R. ; de Klerk, J. M. H. ; Bloemendal, H. J. ; Hendrikse, H. N. Bone 2017, 105, 315.

    9. [9]

      (a) Spacek, P. ; Keough, D. T. ; Chavchich, M. ; Dracinsky, M. ; Janeba, Z. ; Naesens, L. ; Edstein, M. D. ; Guddat, L. W. ; Hockova, D. Bioorg. Med. Chem. 2017, 25, 4008.
      (b) Lan, X. ; Xie, D. ; Yin, L. ; Wang, Z. ; Chen, J. ; Zhang, A. ; Song, B. ; Hu, D. Bioorg. Med. Chem. Lett. 2017, 27, 4270.
      (c) Skorenski, M. ; Pachota, M. ; Pyrc, K. ; Sienczyk, M. ; Oleksyszyn, J. Antivir. Res. 2017, 144, 286.
      (d) Veleti, K. ; Petit, C. ; Ronning, D. R. ; Sucheck, S. J. Org. Biomol. Chem. 2017, 15, 3884.

    10. [10]

      Babinski, D. J.; Aguilar, H. R.; Still, R.; Frantz, D. E. J. Org. Chem. 2011, 76, 5915.  doi: 10.1021/jo201042c

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