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

a.
Ministry of Education of China), Hunan Normal University, Changsha 410081
b.
Key Laboratory of the Assembly and Application of Organic Functional Molecules, Hunan Normal University, Changsha 410081

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.
- synthesis,
- base,
- cyclization,
- pyrano[3, 2-c]pyrazol-7(1H)-one,
- phosphonate
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
1. [1]
  Lifang HE , Yaoze LUO , Qiying SHI , Jianxin TANG , Fuxing ZHANG , Xiaoming ZHU . Synthesis, structure, and properties of hydrated tricyclohexyltin theophylline-7-acetic acid complex. Chinese Journal of Inorganic Chemistry, 2026, 42(3): 632-640. doi: 10.11862/CJIC.20250244
2. [2]
  Liping GUO . Synthesis and crystal structure characterization of yttrium imido complex: The reactivity of 2-substituted-1-amino-o-carborane with yttrium dialkyl complex. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1409-1415. doi: 10.11862/CJIC.20250065
3. [3]
  Ran ZHUANG , Xinru WANG , Ruwei SHEN , Dunru ZHU . Syntheses, crystal structures and Hirshfeld surface analyses of three 3-pyridazinyl-substituted triaryltriazoles and their Cu(Ⅱ) complexes. Chinese Journal of Inorganic Chemistry, 2026, 42(8): 1712-1722. doi: 10.11862/CJIC.20260136
4. [4]
  Qing ZHANG , Kexin ZHOU , Yanjun GUO , Guangjun CHEN , Bai HE , Bo YU , Songshan JIANG , Guoyuan YUAN , Huidong QIU . Preparation, functional modification, and applications of Fe₃O₄ nanoparticles. Chinese Journal of Inorganic Chemistry, 2026, 42(7): 1383-1411. doi: 10.11862/CJIC.20250344
5. [5]
  Lifang HE , Wenjie TANG , Yaoze LUO , Mingsheng LIANG , Jianxin TANG , Yuxuan WU , Fuxing ZHANG , Xiaoming ZHU . Synthesis, structure, and anticancer activity of two dialkyltin complexes constructed based on 2, 2′-bipyridin-6, 6′-dicarboxylic acid. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1601-1609. doi: 10.11862/CJIC.20250012
6. [6]
  Yuanyu YANG , Jianhua XUE , Yujia BAI , Lulu CUI , Dongdong YANG , Qi MA . Design, synthesis, and detection of Al³⁺ of two zinc complexes based on Schiff base ligands. Chinese Journal of Inorganic Chemistry, 2025, 41(6): 1207-1216. doi: 10.11862/CJIC.20250005
7. [7]
  Guo-Cai Yuan , Ming-Gang Li , Sha Yang , Kanghui Song , Chen-Xu Gong , Shuang-Jun Zhu , Yuanming Li , Ke-Yin Ye . Electrophotocatalytic decarbonylative [4+2] cyclization of indenones. Chinese Chemical Letters, 2026, 37(6): 111709-. doi: 10.1016/j.cclet.2025.111709
8. [8]
  Xiaofen GUAN , Yating LIU , Jia LI , Yiwen HU , Haiyuan DING , Yuanjing SHI , Zhiqiang WANG , Wenmin WANG . Synthesis, crystal structure, and DNA-binding of binuclear lanthanide complexes based on a multidentate Schiff base ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2486-2496. doi: 10.11862/CJIC.20240122
9. [9]
  Fengqing Wang , Changxing Qi , Chunmei Chen , Qin Li , Qingyi Tong , Weiguang Sun , Zhengxi Hu , Minyan Wang , Hucheng Zhu , Lianghu Gu , Yonghui Zhang . Discovery and enantioselective total synthesis of antitumor agent asperfilasin A via a regio- and diastereoselective Nazarov cyclization. Chinese Chemical Letters, 2025, 36(6): 110252-. doi: 10.1016/j.cclet.2024.110252
10. [10]
  Qi Wang , Bichu Cheng , Minjie Liu , Fen-Er Chen . A concise asymmetric synthesis of (–)-oseltamivir phosphate via a biphasic Pd-catalyzed Heck-type cyclization. Chinese Chemical Letters, 2026, 37(5): 111555-. doi: 10.1016/j.cclet.2025.111555
11. [11]
  Wenxiong Yu , Chenyu Yang , Xian Feng , Chengshuo Shen . Scholl cyclization of [6]helicenes into negatively curved hexa[7]circulenes. Chinese Chemical Letters, 2025, 36(11): 110939-. doi: 10.1016/j.cclet.2025.110939
12. [12]
  Maitri Bhattacharjee , Rekha Boruah Smriti , R. N. Dutta Purkayastha , Waldemar Maniukiewicz , Shubhamoy Chowdhury , Debasish Maiti , Tamanna Akhtar . Synthesis, structural characterization, bio-activity, and density functional theory calculation on Cu(Ⅱ) complexes with hydrazone-based Schiff base ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1409-1422. doi: 10.11862/CJIC.20240007
13. [13]
  Heng Qiu , Wang Xie , Mingxia Ye , Conghao Shi , Juli Jiang , Zhouyu Wang , Wim Dehaen , Leyong Wang . Reaction-driven crystallization: Gram-scale synthesis of chiral macrocycles bearing Tröger's base with self-sorting. Chinese Chemical Letters, 2026, 37(7): 111966-. doi: 10.1016/j.cclet.2025.111966
14. [14]
  Xinting XIONG , Zhiqiang XIONG , Panlei XIAO , Xuliang NIE , Xiuying SONG , Xiuguang YI . Synthesis, crystal structures, Hirshfeld surface analysis, and antifungal activity of two complexes Na(Ⅰ)/Cd(Ⅱ) assembled by 5-bromo-2-hydroxybenzoic acid ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1661-1670. doi: 10.11862/CJIC.20240145
15. [15]
  Jing WU , Puzhen HUI , Huilin ZHENG , Pingchuan YUAN , Chunfei WANG , Hui WANG , Xiaoxia GU . Synthesis, crystal structures, and antitumor activities of transition metal complexes incorporating a naphthol-aldehyde Schiff base ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2422-2428. doi: 10.11862/CJIC.20240278
16. [16]
  Bin SUN , Heyan JIANG . Glucose-modified bis-Schiff bases: Synthesis and bio-activities in Alzheimer′s disease therapy. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1338-1350. doi: 10.11862/CJIC.20240428
17. [17]
  Lixing ZHANG , Yaowen WANG , Xu HAN , Junhong ZHOU , Jinghui WANG , Liping LI , Guangshe LI . Research progress in the synthesis of fluorine-containing perovskites and their derivatives. Chinese Journal of Inorganic Chemistry, 2025, 41(9): 1689-1701. doi: 10.11862/CJIC.20250007
18. [18]
  Changming Li , Hongdan Zhu , Can-Can Bao , Yongjia Lin , Bing-Tao Guan , Qian Peng . Mechanistic insights for Aryl dilithium base enables the acylation of unactivated C_sp3–H. Chinese Chemical Letters, 2025, 36(9): 110809-. doi: 10.1016/j.cclet.2024.110809
19. [19]
  Yingyue ZHANG , Liuqing KANG , Yating YANG , Xiaofen GUAN , Wenmin WANG . Crystal structure and antibacterial activity of two Gd₂ complexes based on polydentate Schiff-base ligands. Chinese Journal of Inorganic Chemistry, 2025, 41(9): 1867-1877. doi: 10.11862/CJIC.20250100
20. [20]
  Yuanfei Liu , Wanjiao Wei , Xu Liu , Rui Hua , Yanjuan Liu , Yuefei Zhang , Wei Chen , Sheng Tang . Green and mild synthesis of Ca-MOF/COF functionalized silica microspheres in an acid-base tunable deep eutectic solvent for multi-mode chromatography. Chinese Chemical Letters, 2026, 37(1): 111186-. doi: 10.1016/j.cclet.2025.111186

Get Citation

PDF

XML

Metrics

PDF Downloads(11)
Abstract views(1798)
HTML views(371)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142