Citation: Lu Shengle, Tu Xianxia, Liu Weishun, Shen Liting, Mao Shanjian, Deng Guisheng. Transition Metal-Free-Catalyzed Regioselective Reversal in the Cyclization of 2-Diazo-3, 5-dioxo-6-ynoates/ynones/ynamide: Synthesis of Diazo γ-Pyrones and Diazo 3(2H)-Furanones[J]. Chinese Journal of Organic Chemistry, ;2018, 38(7): 1663-1672. doi: 10.6023/cjoc201712014 shu

Transition Metal-Free-Catalyzed Regioselective Reversal in the Cyclization of 2-Diazo-3, 5-dioxo-6-ynoates/ynones/ynamide: Synthesis of Diazo γ-Pyrones and Diazo 3(2H)-Furanones

Key Laboratory of Chemical Biology and Traditional Chinese Medicine Research, Ministry of Education, Hunan Normal University, Changsha 410081;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: 7 December 2017
Revised Date: 6 March 2018
Available Online: 12 July 2018
Fund Project: Project supported by the National Natural Science Foundation of China (No. 21372071) and the Hunan Provincial Natural Science Foundation (No. 2016JJ2080)the National Natural Science Foundation of China 21372071the Hunan Provincial Natural Science Foundation 2016JJ2080

Figures(4)

For HSbF₆/EtOH system, diazo γ-pyrones were cleanly obtained starting from 2-diazo-3, 5-dioxo-6-ynoates/ynones/ynamide at 80℃, whereas diazo 3(2H)-furanones were predominantly generated in HOAc-Et₃N-1, 2-dichloroethane system at 25℃. These diazo compounds can undergo an efficient Rh(Ⅱ)-catalyzed intermolecular cyclopropanation with alkene.
- diazo γ-pyrone,
- diazo 3(2H)-furanone,
- synthesis,
- cyclopropanation,
- regioselectivity
1. [1]
  For 4-pyrone see: (a) Caturla, F. ; Jiménez, J. -M. ; Godessart, N. ; Amat, M. ; Cárdenas, A. ; Soca, L. ; Beleta, J. ; Ryder, H. ; Crespo, M. I. J. Med. Chem. 2004, 47, 3874.
  (b) Abe, I. ; Utsumi, Y. ; Oguro, S. ; Morita, H. ; Sano, Y. ; H. J. Am. Chem. Soc. 2005, 127, 1362.
  (c) Puerta, D. T. ; Mongan, J. ; Tran, B. L. ; McCammon, J. A. ; Cohen, S. M. J. Am. Chem. Soc. 2005, 127, 14148.
  (d) Sibi, M. P. ; Zimmerman, J. J. Am. Chem. Soc. 2006, 128, 13346.
  (e) Hollick, J. J. ; Rigoreau, L. J. ; Cano-Soumillac, C. ; Cockcroft, X. ; Curtin, N. J. ; Frigerio, M. ; Golding, B. T. ; Guiard, S. ; Hardcastle, I. R. ; Hickson, I. J. Med. Chem. 2007, 50, 1958.
  For 3(2H)-furanone see: (f) Li Y. ; Hale K. J. Org. Lett. 2007, 9, 1267.
  (g) Mitchell, J. M. ; Finney, N. S. Org. Biomol. Chem. 2005, 3, 4274.
  (h) Hayashi, Y. ; Shoji, M. ; Yamaguchi, S. ; Mukaiyama, T. ; Yamaguchi, J. ; Kakeya, H. ; Osada, H. Org. Lett. 2003, 5, 2287.
2. [2]
  (a) Yamamura, S. ; Nishiyama, S. Bull. Chem. Soc. Jpn. 1997, 70, 2025.
  (b) Sharma, P. ; Powell, K. J. ; Burnley, J. ; Awaad, A. S. ; Moses, J. E. Synthesis 2011, 2865.
  (c) Hayakawa, I. ; Takemura, T. ; Fukasawa, E. ; Ebihara, Y. ; Sato, N. ; Nakamura, T. ; Suenaga, K. ; Kigoshi, H. Bull. Chem. Soc. Jpn. 2012, 85, 1077.
  (d) Martens, S. ; Mithofer, A. Phytochemicals 2005, 66, 2399.
  (e) Veitch, N. C. ; Grayer, R. J. Nat. Prod. Rep. 2008, 25, 555.
  (f) Crozier, A. ; Jaganath, I. B. ; Clifford, M. N. Nat. Prod. Rep. 2009, 26, 1001.
  (g) Hansen, M. R. ; Hurley, L. H. Acc. Chem. Res. 1996, 29, 249.
3. [3]
  For 4-pyrone see: (a) Grarey, D. ; Ramirez, M. ; Gonzales, S. ; Wertsching, A. ; Tith, S. ; Keefe, K. ; Pea, M. R. J. Org. Chem. 1996, 61, 4853.
  (b) Ishibashi, Y. ; Ohba, S. ; Nishiyama, S. ; Yamamura, S. Tetrahedron Lett. 1996, 37, 2997.
  (c) Jo, Y. J. ; Cho, I. H. ; Song, C. K. ; Shin, H. W. ; Kim, Y. S. J. Food Sci. 2011, 76, C368.
  (d) Li, D. -F. ; Hu, P. -P. ; Liu, M. -S. ; Kong, X. -L. ; Zhang, J. -C. ; Hider, R. C. ; Zhou, T. J. Agric. Food. Chem. 2013, 61, 6597.
  (e) Shahrisa, A. ; Esmati, S. ; Miri, R. ; Firuzi, O. ; EdrakiN, N. ; Nejati, M. Eur. J. Med. Chem. 2013, 66, 388.
  For 3(2H)-furanone see: (f) Shin, S. S. ; Byun, Y. ; Lim, K. M. ; Choi, J. K. ; Lee, K. -W. ; Moh, J. H. ; Kim, J. K. ; Jeong, Y. S. ; Kim, J. Y. ; Choi, Y. H. ; Koh, H. -J. ; Park, Y. -H. ; Oh, Y. I. ; Noh, M. -S. ; Chung, S. J. Med. Chem. 2004, 47, 792.
4. [4]
  Kankanala, J.; Kirby, K. A.; Liu, F.; Miller, L.; Nagy, E.; Wilson, D. J.; Parniak, M. A.; Sarafianos, S. G.; Wang, Z. J. Med. Chem. 2016, 59, 5051. doi: 10.1021/acs.jmedchem.6b00465
5. [5]
  For 4-pyrone see: (a) Obydennov, D. L. ; Pan'kina, E. O. ; Sosnovskikh, V. Y. J. Org. Chem. 2016, 81, 12532.
  (b) Dong, S. ; Fang, C. ; Tang, W. ; Lu, T. ; Du, D. Org. Lett. 2016, 18, 3882.
  (c) Henrot, M. ; Jean, A. ; Peixoto, P. A. ; Maddaluno, J. ; Paolis, M. D. J. Org. Chem. 2016, 81, 5190.
  (d) Danda, A. ; Kesave-Reddy, N. ; Golz, C. ; Strohmann, C. ; Kumar, K. Org. Lett. 2016, 18, 2632.
  (e) Beye, G. E. ; Karagiannis, A. ; Kazemeini, A. ; Ward, D. E. Can. J. Chem. 2012, 90, 954.
  For 3(2H)-furanone see: (f) Sadamitsu, Y. ; Komatsuki, K. ; Saito, K. ; Yamada, T. Org. Lett. 2017, 19, 3191.
  (g) Qiu, H. ; Deng, Y. ; Marichev, K. O. ; Doyle, M. P. J. Org. Chem. 2017, 82, 1584.
  (h) He, H. ; Qi, C. ; Hu, X. ; Ouyang, L. ; Xiong, W. ; Jiang, H. J. Org. Chem. 2015, 80, 4957.
  (i) Inagaki, S. ; Nakazato, M. ; Fukuda, N. ; Tamura, S. ; Kawano, T. J. Org. Chem. 2017, 82, 5583.
6. [6]
  (a) Marei, M. G. ; El-Ghanam, M. Phosphorus, Sulfur, Silicon Relat. Elem. 1995, 107, 1.
  (b) Marei, M. G. ; El-Ghanam, M. Bull. Chem. Soc. Jpn. 1992, 65, 3509.
  (c) Marei, M. G. ; Aly, D. M. ; Mishrikey, M. M. Bull. Chem. Soc. Jpn. 1992, 65, 3419.
  (d) Marei, M. G. ; Mishrikey, M. M. ; El-Kholy, I. E. J. Heterocycl. Chem. 1986, 23, 1849.
  (e) El-Kholy, I. E. ; Mishrikey, M. M. ; Marei, M. G. J. Heterocycl. Chem. 1982, 19, 1421.
  (f) Kuroda, H. ; Izawa, H. Chin. J. Chem. 2008, 26, 1944.
  (g) Yoshida, M. ; Fujino, Y. ; Doi, T. Org. Lett. 2011, 13, 4526.
  (h) Yoshida, M. ; Fujino, Y. ; Saito, K. ; Doi, T. Tetrahedron 2011, 67, 9993.
  (i) Kuroda, H. ; Izawa, H. Bull. Chem. Soc. Jpn. 2007, 80, 780.
  (j) Preindl, J. ; Jouvin, K. ; Laurich, D. ; Seidel, G. ; Fürstner, A. Chem. -Eur. J. 2015, 21, 1.
  (k) García, H. ; Iborra, S. ; Primo, J. ; Miranda, M. A. J. Org. Chem. 1986, 51, 4432.
  (l) Brennan, C. M. ; Johnson, C. D. ; McDonnell, P. D. J. Chem. Soc., Perkin Trans. 2 1989, 957.
  (m) Liu, C. ; Zhang, Z. ; Zhang, J. ; Liu X. ; Xie, M. Chin. J. Chem. 2014, 32, 1233.
7. [7]
  Doyle, M. P. ; McKervey, M. A. ; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds, Wiley, New York, 1998.
8. [8]
  Wang, F.; Lu, S.; Chen, B.; Zhou, Y.; Yang, Y.; Deng, G. Org. Lett. 2016, 18, 6248. doi: 10.1021/acs.orglett.6b02973
9. [9]
  Deng, G.; Wang, F.; Lu, S.; Cheng, B. Org. Lett. 2015, 17, 4651. doi: 10.1021/acs.orglett.5b02369
10. [10]
  (a) Yoshida, M. ; Fujino, Y. ; Doi, T. Org. Lett. 2011, 13, 4526.
  (b) Preindl, J. ; Jouvin, K. ; Laurich, D. ; Seidel, G. ; Fürstner, A. Chem.-Eur. J. 2016, 22, 237.
11. [11]
  Vasilyev, A. V.; Walspurger, S.; Chassaing, S.; Pale, P.; Sommer, J. Eur. J. Org. Chem. 2007, 5740.
12. [12]
  Vasilyev, A. V.; Walspurger, S.; Haouas, M.; Sommer, J.; Pale, P.; Rudenko, A. P. Org. Biomol. Chem. 2004, 2, 3483. doi: 10.1039/b412323a
13. [13]
  (a) Kawata, M. ; Ten-no, S. ; Kato, S. ; Hirata, F. J. Phys. Chem. 1996, 100, 1111.
  (b) Bordwell, F. G. ; McCallum, R. J. ; Olmstead, W. N. J. Org. Chem. 1984, 49, 1424.
  (c) Shukla, S. K. ; Kumar, A. J. Phys. Chem. B 2013, 117, 2456.
  (d) Bachrach, S. M. ; Dzierlenga, M. W. J. Phys. Chem. A 2011, 115, 5674.
  (e) Murłowska, K. ; Sadlej-Sosnowska, N. J. Phys. Chem. A 2005, 109, 5590.
1. [1]
  Shihui Shi , Haoyu Li , Shaojie Han , Yifan Yao , Siqi Liu . Regioselectively Synthesis of Halogenated Arenes via Self-Assembly and Synergistic Catalysis Strategy. University Chemistry, 2024, 39(5): 336-344. doi: 10.3866/PKU.DXHX202312002
2. [2]
  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
3. [3]
  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
4. [4]
  Junyuan Zhang , Xiangzheng Ren , Zhiwei Miao . 烯烃1,3-双官能团化反应研究进展. University Chemistry, 2026, 41(8): 148-161. doi: 10.12461/PKU.DXHX202507121
5. [5]
  Danqing Wu , Jiajun Liu , Tianyu Li , Dazhen Xu , Zhiwei Miao . Research Progress on the Simultaneous Construction of C—O and C—X Bonds via 1,2-Difunctionalization of Olefins through Radical Pathways. University Chemistry, 2024, 39(11): 146-157. doi: 10.12461/PKU.DXHX202403087
6. [6]
  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
7. [7]
  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
8. [8]
  Ying Chen , Ronghua Yan , Weiyan Yin . Research Progress on the Synthesis of Metal Single-Atom Catalysts and Their Applications in Electrocatalytic Hydrogen Evolution Reactions. University Chemistry, 2025, 40(9): 344-353. doi: 10.12461/PKU.DXHX202503066
9. [9]
  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
10. [10]
  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
11. [11]
  Jiaming Xu , Yu Xiang , Weisheng Lin , Zhiwei Miao . Research Progress in the Synthesis of Cyclic Organic Compounds Using Bimetallic Relay Catalytic Strategies. University Chemistry, 2024, 39(3): 239-257. doi: 10.3866/PKU.DXHX202309093
12. [12]
  Yaqin Zheng , Lian Zhuo , Meng Li , Chunying Rong . Enhancing Understanding of the Electronic Effect of Substituents on Benzene Rings Using Quantum Chemistry Calculations. University Chemistry, 2025, 40(3): 193-198. doi: 10.12461/PKU.DXHX202406119
13. [13]
  Xinyi Zhang , Kai Ren , Yanning Liu , Zhenyi Gu , Zhixiong Huang , Shuohang Zheng , Xiaotong Wang , Jinzhi Guo , Igor V. Zatovsky , Junming Cao , Xinglong Wu . Progress on Entropy Production Engineering for Electrochemical Catalysis. Acta Physico-Chimica Sinica, 2024, 40(7): 2307057-0. doi: 10.3866/PKU.WHXB202307057
14. [14]
  Lei Feng , Ze-Min Zhu , Ying Yang , Zongbin He , Jiafeng Zou , Man-Bo Li , Yan Zhao , Zhikun Wu . Long-Pursued Structure of Au₂₃(S-Adm)₁₆ and the Unexpected Doping Effects. Acta Physico-Chimica Sinica, 2024, 40(5): 2305029-0. doi: 10.3866/PKU.WHXB202305029
15. [15]
  Chunling Qin , Shuang Chen , Hassanien Gomaa , Mohamed A. Shenashen , Sherif A. El-Safty , Qian Liu , Cuihua An , Xijun Liu , Qibo Deng , Ning Hu . Regulating HER and OER Performances of 2D Materials by the External Physical Fields. Acta Physico-Chimica Sinica, 2024, 40(9): 2307059-0. doi: 10.3866/PKU.WHXB202307059
16. [16]
  Yunhao Zhang , Yinuo Wang , Siran Wang , Dazhen Xu . Progress in Selective Construction of Functional Aromatics from Nitrogenous Cycloalkanes. University Chemistry, 2024, 39(11): 136-145. doi: 10.3866/PKU.DXHX202401083
17. [17]
  Guanghuan Chen , Yinghua Wang , Jinhui Ming , Jian Ling , Zhihui Shao , Chongdao Lu , Yong Shi . 香芹酮β硼化：一个可用于展示反应选择性的教学实验. University Chemistry, 2026, 41(5): 101-108. doi: 10.12461/PKU.DXHX202510042
18. [18]
  Yi Huang , Yansong Xiao , Xingxing Ma , Qiuling Song . Zweifel olefination: an innovative approach to highly efficient stereoselective alkene synthesis. University Chemistry, 2026, 41(7): 119-125. doi: 10.12461/PKU.DXHX202506046
19. [19]
  Hong RAO , Yang HU , Yicong MA , Chunxin LÜ , Wei ZHONG , Lihua DU . Synthesis and in vitro anticancer activity of phenanthroline-functionalized nitrogen heterocyclic carbene homo- and heterobimetallic silver/gold complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2429-2437. doi: 10.11862/CJIC.20240275
20. [20]
  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

Get Citation

PDF

XML

Metrics

PDF Downloads(14)
Abstract views(1787)
HTML views(207)

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