综述与进展

慕尼黑酮研究最新进展

  • 苗群 ,
  • 孙怀林
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  • 南开大学化学系 元素有机化学国家重点实验室 化学与工程协同创新中心 天津 300071

收稿日期: 2015-11-25

  修回日期: 2015-12-21

  网络出版日期: 2016-01-21

基金资助

国家自然科学基金(No.20834002)和天津市自然科学基金(No.08JCZDJC21600)资助项目.

Recent Progresses in the Chemistry of Münchnones

  • Miao Qun ,
  • Sun Huailin
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  • State Key Laboratory of Elemento-Organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering Tianjin, Department of Chemistry, Nankai University, Tianjin 30071

Received date: 2015-11-25

  Revised date: 2015-12-21

  Online published: 2016-01-21

Supported by

Project supported by the National Natural Science Foundation of China (No. 20834002) and the Natural Sciences Foundation of Tianjin City (No. 08JCZDJC21600).

摘要

慕尼黑酮是一种介离子型五元杂环化合物,在杂环化学乃至有机化学中占有着重要地位.自从1964年Huisgen发现并命名这类化合物以来,其合成、性质和应用的研究吸引了越来越多的兴趣.它的重要性质之一是可以作为1,3-偶极体与不饱和键发生环加成反应,该反应现已成为合成吡咯及其它一些杂环化合物的一种重要方法.近年来,人们开始通过金属有机反应来实现慕尼黑酮的合成,慕尼黑酮新的反应性质得到进一步探索,慕尼黑酮在有机合成上的应用也越来越普遍.对慕尼黑酮研究最新进展进行了总结.

本文引用格式

苗群 , 孙怀林 . 慕尼黑酮研究最新进展[J]. 有机化学, 2016 , 36(5) : 913 -926 . DOI: 10.6023/cjoc201511047

Abstract

Münchnones are mesoionic five-membered heterocycles, which play an important role in heterocycles as well as in organic chemistry. Since they were discovered by Huisgen in 1964, there has been growing interest in syntheses, properties and application of münchnones. One of the most significant properties of münchnones is that they can undergo cycloaddition reactions to unsaturated bonds as 1,3-dipoles. This reaction has become an important method for the synthesis of pyrroles and other heterocycles. Recently, remarkable progresses have been achieved in the synthesis of münchnones by means of organo-metallic reactions, the new reactive properties of münchnones have also been explored, and the application of münchnones in organic synthesis has been widely reported. In this review, these recent progresses in the chemistry of münchnone are summarized.

参考文献

[1] Miao, Q.; Sun, H.-L. Chin. Sci.Bull.2015, 60, 2003 (in Chinese).
(苗群, 孙怀林, 科学通报, 2015, 60, 2003. )
[2] Huisgen, R.; Gotthardt, H.; Bayer, H. O. Angew. Chem., Int. Ed.1964, 3, 136.
[3] Bayer, H. O.; Huisgen, R.; Knorr, R.; Schaefer, F. C. Chem. Ber.1970, 103, 2581.
[4] Potts, K. T.; Yao, S. J. Org. Chem.1979, 44, 977.
[5] Anderson, A. K.; Heider, A. R. Synth.Commun.1986, 16, 357.
[6] (a) Kato, H.; Tani, K.; Kurumisawa, H.; Tamura, Y. Chem.Lett.1980, 717.
(b) Kawase, M. J. Chem. Soc., Chem. Commun.1990, 1328.
[7] Huisgen, R.; Gotthardt, H.; Bayer, H. O.; Schaefer, F. C. Chem. Ber.1970, 103, 2611.
[8] (a) Gotthardt, H.; Huisgen, R.; Schaefer, F. C. Tetrahedron Lett.1964, 10, 487.
(b) Gotthardt, H.; Huisgen, R. Chem. Ber.1970, 103, 2625.
[9] (a) Turchi, I. J.; Dewar, M. J. S. Chem.Rev.1975, 75, 389.
(b) Turchi, I. J. Ind. Eng. Chem.Prod. Res. Dev.1981, 20, 32.
[10] Gingrich, H. L.; Baum, J. S. In Chemistry of Heterocyclic Compounds: Oxazoles,Vol. 45. Eds.: Turchi, I. J., Wiley, New York, 1986, pp. 731~922.
[11] Gribble, G. W. In Oxazoles: Synthesis, Reactions, and Spectroscopy,Vol. 60, Ed.: Palmer, D. C., Wiley, New York, 2003, pp. 473~534.
[12] Gribble, G. W. In Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry toward Heterocycles and Natural Products,Vol. 59, Eds.: Padwa, A.; Pearson. W. H., Wiley, New York, 2002, pp. 680~753.
[13] (a) Ollis, W. D.; Ramsden, C. A. Adv. Heterocycl. Chem.1976, 19, 1.
(b) Newton, C. G.; Ramsdem, C. A. Tetrahedron 1982, 38, 2965.
(c) Boyd, G. A. In Comprehensive Heterocyclic Chemistry, Vol. 6,Eds.: Katritzky, A. R.; Rees, C. W., Elsevier, Oxford, 1984, pp. 206~210.
(d) Ollis, W. D.; Stanforth, S. D.; Ramsdem, C. A. Tetrahedron 1985, 41, 2239.
(e) Kato, H.; Kobayashi, T. J. Synth.Org. Chem. Jpn.1990, 48, 672.
(f) Hartner, F. W. Jr. In Comprehensive Heterocyclic Chemistry II,Vol. 3, Ed.: Katritzky, A. R.; Rees, C. W.; Scriven, E. F. V., Elsevier, Oxford, 1996, pp. 284~286.
(g) Fortt, S. M. In Rodd's Chemistry of Carbon Compounds,Vol. IV C/D, Suppl. 2 to 2nd ed., Ed.: Sainsbury, M., Elsevier, Amsterdam, 1998, pp. 49~57.
(h) Gupta, R. R.; Kumar, M.; Gupta, V. Heterocyclic Chemistry II, Springer, Berlin, 1999, pp. 587~597.
(i) Yeh, V.; Iyengar, R. In Comprehensive Heterocyclic Chemistry III, Vol. 4, Eds: Katritzky. A. R.; Ramsden, C. A.; Scriven, E. F. V.; Taylor, R. J. K., Elsevier, Oxford, 2008, pp. 502~503.
(j) Lopchuk, J. M. In Metalation of Azoles and Related Five-Membered Ring Heterocycles, Eds.: Gribble, G. W., Springer, Berlin, 2012, pp. 399~402.
[14] Reissig, H-U.; Zimmer, R. Angew.Chem., Int. Ed.2014, 53, 9708.
[15] (a) Arndtsen, B. A. Chem. Eur. J.2009, 15, 302.
(b) Quesenel, J. S.; Arndtsen, B. A. Pure Appl.Chem.2013, 85, 377.
[16] (a) Dghaym, R. D.; Dhawan, R.; Arndtsen, B. A. Angew. Chem., Int. Ed.2001, 40, 3228.
(b) Bontemps, S.; Quesnel, J. S.; Worrall, K.; Arndtsen, B. A. Angew. Chem., Int. Ed.2011, 50, 8948.
(c) Worrall, K.; Xu, B.; Bontemps, S.; Arndtsen, B. A. J. Org.Chem.2011, 76, 170.
[17] Dhawan, R.; Dghaym, R. D.; Arndtsen, B. A. J. Am.Chem. Soc.2003, 125, 1474.
[18] Dhawan, R.; Arndtsen, B. A. J. Am.Chem. Soc.2004, 126, 468.
[19] Siamaki, A. R.; Arndtsen, B. A. J. Am.Chem. Soc.2006, 128, 6050.
[20] Dhawan, R.; Dghaym, R. D.; St Cyr, D. J.; Arndtsen, B. A. Org. Lett.2006, 8, 3927.
[21] Estévez, V.; Villacampa, M.; Menéndez, J. C. Chem. Soc. Rev.2010, 39, 4402.
[22] Siamaki, A. R.; Sakalauskas, M.; Arndtsen, B. A. Angew. Chem., Int. Ed.2011, 50, 6552.
[23] Leitch, D. C.; Kayser, L. V.; Han, Z. -Y.; Siamaki, A. R.; Keyzer, E. N.; Gefen, A.; Arndtsen, B. A. Nat.Commun.2015, 6, 7411.
[24] Lu, Y.; Arndtsen, B. A. Angew.Chem., Int. Ed.2008, 47, 5430
[25] (a) Sun, H.-L.; Zhang, J.; Liu, Q.-H.; Yu, L.; Zhao, J.-Y. Angew. Chem., Int. Ed.2007, 46, 6068.
(b) Zhang, Y.-P.; Sun, H.-L. Chem. J. Chin. Univ. 2014, 35, 54 (in Chinese).
(张永坡, 孙怀林, 高等学校化学学报, 2014, 35, 54.)
[26] Miao, Q. M.S. Thesis, Nankai University, Tianjin, 2015 (in Chinese).
(苗群, 硕士论文, 南开大学, 天津, 2015.)
[27] Lopchuk, J. M.; Gribble, G.. W. Tetrahedron Lett.2011, 52, 4106.
[28] Lopchuk, J. M.; Gribble, G.. W. Heterocycles 2011, 82, 1617.
[29] Pechenkin, S. Y.; Starosotnikov, A. M.; Bastrakov, M. A.; Kachala, V. V.; Shevelev, S. A. Mendeleev Commun.2012, 22, 35.
[30] Lopchuk, J. M.; Hughes, R. P.; Gribble, G.. W. Org. Lett.2013, 15, 5218.
[31] Lopchuk, J. M.; Song, M.; Butler, B.; Gribble, G. W. Synthesis 2015, 47, 2776.
[32] Grassi, G.; Foti, F.; Risitano, F.; Zona, D. Tetrahedron Lett.2005, 46, 1061.
[33] Bélanger, G..; April, M.; Dauphin, É.; Roy, S. J. Org. Chem.2007, 72, 1104.
[34] Cordaro, M.; Grassi, G.; Risitano, F.; Scala, A. Tetrahedron 2010, 66, 2713.
[35] (a) Cordaro, M.; Grassi, G.; Rescifina, A.; Chiacchio, U.; Risitano, F.; Scala, A. Tetrahedron 2011, 67, 608.
(b) Cordaro, M.; Grassi, G.; Rescifina, A.; Chiacchio, U.; Risitano, F.; Scala, A. J. Mol. Struct.2011, 991, 143.
[36] (a) Mazgarova, G. G.; Fatykhov, A. A.; Gataullin, R. R. Russ. J. Org. Chem.2014, 50, 1155.
(b) Mazgarova, G. G.; Fatykhov, A. A.; Gataullin R. R. Russ. J. Org. Chem.2014, 50, 1346.
[37] Gerster, H.; Maas, G. Z. Naturforsch.2008, 63b, 384.
[38] Harju, K.; Manevski, N.; Yli-Kauhaluoma, J. Tetrahedron 2009, 65, 9702.
[39] Fang, Y.; Larock, R. C.; Shi, F. Asian J. Org.Chem.2014, 3, 55.
[40] Lopchuk, J. M.; Gribble, G. W. Tetrahedron Lett.2014, 55, 2809.
[41] (a) Lira, B. F.; De Athayde Filho, P. F.; Miller, J.; Simas, A. M.; De Farias Dias, A.; Vieira, M. J. Molecules 2002, 7, 791.
(b) De Athayde Filho, P. F.; Miller, J.; Simas, A. M.; Lira, B. F.; De Souza Luis, J. A.; Zuckerman Schpector, J. Synthesis 2003, 685.
[42] Cantillo, D.; Ávalos, M.; Babiano, R.; Cintas, P.; Jiménez, J. L.; Light, M. E.; Palacios, J. C.; Rodríguez, V. Org. Biomol. Chem.2010, 8, 5367.
[43] Cantillo, D.; Ávalos, M.; Babiano, R.; Cintas, P.; Jiménez, J. L.; Light, M. E.; Palacios, J. C.; Porro, R. J. Org. Chem.2014, 79, 4201.
[44] Grassi, G.; Risitano, F.; Foti, F.; Cordaro, M.; Bruno, G.; Nicolò, F. Chem.Commun.2003, 1868.
[45] Kazhkennov, Z.-G. M.; Bush, A. A.; Babaev, E. V. Molecules 2005, 10, 1109.
[46] Kawase, M.; Koiwai, H.; Tanaka, T.; Tani, S.; Miyamae, H. Heterocycles 2001, 55, 1919.
[47] Saijo, R.; Hagimoto, Y.; Kawase, M. Org.Lett.2010, 12, 4776.
[48] Saijo, R.; Kawase, M. Tetrahedron Lett.2012, 53, 2782.
[49] Saijo, R.; Kurihara, K.; Akira, K.; Kawase, M. Heterocycles 2013, 87, 115.
[50] Saijo, R.; Kurihara, K.; Akira, K.; Uno, H.; Kawase, M. Tetrahedron Lett.2013, 54, 4418.
[51] Samanta, S. K.; Yli-Kauhaluoma, J. J. Comb. Chem.2005, 7, 142.
[52] Wang, J. K.; Zong, Y. X.; Yue, G. R. Synlett 2005, 1135.
[53] Gao, D.; Zhai, H.; Parvez, M.; Back, T. G. J. Org. Chem.2008, 73, 8057.
[54] Pinho e Melo, T. M. V. D.; Gomes, C. S. B.; Gonsalves, A. M.; Paixão, J. A.; Beja, A. M.; Silva, M. R.; Alte da Veiga, L. Tetrahedron 2002, 58, 5093.
[55] Pinho e Melo, T. M. V. D.; Soares, M. I. L.; Rocha Gonsavles, A. M. d'A.; Paixão, J. A.; Beja, A. M.; Silva, M. R.; Alte da Veiga, L.; Pessoa, J. C. J. Org.Chem.2002, 67, 4045.
[56] Lopes, S. M. M.; Laranjo, M.; Serra, A. C.; Abrantes. A. M.; d'A. Rocha Gonsavles, A. M.; Botelho, M. F.; Beja, A. M.; Silva, M. R.; Pinho e Melo, T. M. V. D. J. Heterocycl. Chem.2010, 47, 960.
[57] Dumitra?cu, F.; Caira, M. R.; Dr?ghici, B.; C?proiu, M. T.; Dumitrescu, D. G. Synlett2008, 813.
[58] Angle, S. R.; Qian, X. L.; Pletnev, A. A. Chin. J. Org.Chem.2007, 72, 2015.
[59] Pandey, P. S.; Rao, T. S. Bioorg. Med. Chem. Lett.2004, 14, 129.
[60] Park, W. K. C.; Kennedy, R. M.; Larsen, S. D.; Miller, S.; Roth, B. D.; Song, Y.; Steinbaugh, B. A.; Sun, K.; Tait, B. D.; Kowala, M. C.; Trivedi, B. K.; Auerbach, B.; Askew, V.; Dillon, L.; Hanselman, J. C.; Lin, Z.; Lu, G. H.; Robertson, A.; Sekerke, C. Bioorg. Med. Chem. Lett.2008, 18, 1151.
[61] Lopchuk, J. M.; Gribble, G. W. Tetrahedron Lett.2015, 56, 3208.
[62] Sugimoto, K.; Miyakawa, Y.; Tokuyama, H. Tetrahedron 2015, 71, 3619.

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