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.
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