Synthesis of 3-Phosphonyl Pyrano[3, 2-c]pyrazol-7(1H)-one
- Corresponding author: Deng Guisheng, gsdeng@hunnu.edu.cn
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
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.
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.
(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.
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
Gelin, S.; Changtegrel, B.; Nadi, A. I. J. Org. Chem. 1983, 48, 4078.
doi: 10.1021/jo00170a041
(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.
Deng, G.; Wang, F.; Lu, S.; Cheng, B. Org. Lett. 2015, 17, 4651.
doi: 10.1021/acs.orglett.5b02369
(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.
(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.
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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