研究简报

4-甲基-2-氧代-6-芳氨基-二氢-吡喃-3-腈衍生物的合成

  • 高宝昌 ,
  • 石雨 ,
  • 田媛 ,
  • 张治国 ,
  • 张婧如 ,
  • 孙宇峰 ,
  • 毛国梁 ,
  • 戴凌燕
展开
  • a 东北石油大学化学化工学院 黑龙江大庆 163319
    b 黑龙江省科学院大庆分院植物化学研究所 黑龙江大庆 163319
    c 黑龙江八一农垦大学生命科学技术学院 黑龙江大庆 163319

收稿日期: 2023-08-12

  修回日期: 2023-10-13

  网络出版日期: 2023-11-08

基金资助

黑龙江省自然科学基金(LH2020B022); 黑龙江省科学院院长基金(YZ2022DQ01); 黑龙江省科学院双提雁阵特别计划基金(YZQY2023DQ01); 黑龙江省省属科研院所科研业务费基金(YS2023DQ02)

Synthesis of 4-Methyl-2-oxo-6-arylamino-2H-pyran-3-carbonitrile Derivatives

  • Baochang Gao ,
  • Yu Shi ,
  • Yuan Tian ,
  • Zhiguo Zhang ,
  • Jingru Zhang ,
  • Yufeng Sun ,
  • Guoliang Mao ,
  • Lingyan Dai
Expand
  • a College of Chemistry and Chemical Engineering, Northeast Petroleum University, Daqing, Heilongjiang 163319
    b Institute of Phytochemistry, Daqing Branch of Heilongjiang Academy of Sciences, Daqing, Heilongjiang 163319
    c College of Science and Biotechnology, Heilongjiang Bayi Agricultural University, Daqing, Heilongjiang 163319
* Corresponding authors. E-mail: ;

Received date: 2023-08-12

  Revised date: 2023-10-13

  Online published: 2023-11-08

Supported by

Heilongjiang Provincial Natural Science Foundation(LH2020B022); Dean Foundation of Heilongjiang Academy of Sciences(YZ2022DQ01); Shuangtiyanzhen Special Plan Foundation of Heilongjiang Academy of Sciences(YZQY2023DQ01); Institutes Scientific Research Foundation of Heilongjiang Provincial Scientific Research(YS2023DQ02)

摘要

2-吡喃酮衍生物在药物领域表现出了巨大的应用潜力, 已有很多该类骨架结构用作合成药物活性分子前体. 因此, 探索新型2-吡喃酮衍生物的合成方法非常重要. 以β-酮酰胺衍生物和氰基乙酸乙酯为原料一步反应合成了2-吡喃酮衍生物, 具有产物收率高(82%~93%)、反应条件温和产物后处理方便等优点, 为2-吡喃酮生物的合成提供了新策略.

本文引用格式

高宝昌 , 石雨 , 田媛 , 张治国 , 张婧如 , 孙宇峰 , 毛国梁 , 戴凌燕 . 4-甲基-2-氧代-6-芳氨基-二氢-吡喃-3-腈衍生物的合成[J]. 有机化学, 2024 , 44(2) : 644 -649 . DOI: 10.6023/cjoc202308010

Abstract

2-Pyrone derivatives have demonstrated considerable potential for usage in the field of medicine. Many of these skeleton structures have been used as precursors in the synthesis of pharmacologically active molecules. As a result, it is critical to explore new approaches for the synthesis of 2-pyrones. A series of 2-pyrone derivatives were synthesized from β-oxo amides and ethyl cyanoacetate through one-step reaction. The methodology offers several significant advantages including mild conditions, ease of handling, and high yields (82%~93%). Such, an efficient synthesis approach for 2-pyrones is provided.

参考文献

[1]
(a) Vara Prasad, J. V. N.; Para, K. S.; Lunney, E. A.; Ortwine, D. F.; Dunbar, J. B., Jr.; Ferguson, D.; Tummino, P. J.; Hupe, D.; Tait, B. D.; Domagala, J. M.; Humblet, C.; Bhat, T. N.; Liu, B.; Guerin, D. M. A.; Baldwin, E. T.; Erickon, J. W.; Swayer, T. K. J. Am. Chem. Soc. 1994, 116, 6989.
[1]
(b) Douglas, C. J.; Sklenicka, H. M.; Shen, H. C.; Mathias, D. S.; Degen, S. I.; Golding, G. M.; Morgan, C. D.; Shih, R. A.; Mueller, K. L.; Seurer, I. M.; Johnson, E. W.; Hsung, R. P. Tetrahedro. 1999, 55, 13683.
[1]
(c) Hagen, S. E.; Vara Prasad, J. V. N.; Boyer, F. E.; Domagala, J. M.; Ellsworth, E. L.; Gjda, C.; Hamilton, H. W.; Markkoski, L. J.; Steinbangh, B. A.; Tit, B. D.; Lunney, E. A.; Tummino, P. J.; Fergnson, D.; Hupe, D.; Nouhan, C.; Gracheck, S. J.; Saunders, J. M.; Vander Roest, S. J. Med. Chem. 1997, 40, 3707.
[2]
(a) Claydon, N.; Allan, M. Trans. Br. Mycol. Soc. 1987, 88, 503.
[2]
(b) Simon, A.; Dunlop, R. W.; Ghisalberti, E. L.; Silvasithamparam, K. Soil Biol. Biochem. 1988, 20, 263.
[2]
(c) You, X. K.; Lin, Z. L.; Zhang, X. L.; Gao, Y. Chin. J. Org. Chem. 2012, 32, 156 (in Chinese).
[2]
(游新奎, 林志兰, 张雪利, 高原, 有机化学. 2012, 32, 156.)
[3]
Liu, Z.; Meinwald, J. J. Org. Chem. 1996, 61, 6693.
[4]
Aytemir, M. D.; Calis, U.; Ozalp, M. Arch. Pharm. Med. Chem. 2004, 337, 281.
[5]
(a) Yao, T.; Larock, R. C. J. Org. Chem. 2003, 68, 5936.
[5]
(b) Fairlamb, I. J. S.; Marrison, L. R.; Dickinson, J. M.; Lu, F. J.; Schmidt, J. P. Bioorg. Med. Chem. 2004, 12, 4285.
[6]
Shi, X.; Leal, W. S.; Liu, Z.; Schrader, E.; Meinwald, J. Tetrahedron Lett. 1995, 36, 71.
[7]
Allen M. Chem. Br. 1996, May, 35.
[8]
Kondoh, M.; Usui, T.; Kobayashi, S.; Tsuchiya, K.; Nishikawa, K.; Nishikiori, T.; Mayumi, T.; Osada, H. Cancer Lett. 1998, 126, 29.
[9]
Kobayashi, S.; Tsuchiya, K.; Kurokawa, T.; Nakagawa, T.; Shimada, N.; Iitaka, Y. J. Antibiot. 1994, 47, 703.
[10]
Tsuchiya, K.; Kobayashi, S.; Nishikiori, T.; Nakagawa, T.; Tatsuta, K. J. Antibiot. 1997, 50, 259.
[11]
(a) Ichihara, A.; Tazaki, H.; Sakamura, S. Tetrahedron Lett. 1983, 48, 5373.
[11]
(b) Chmielewski, M.; Jurczak, J. J. Org. Chem. 1981, 46, 2230.
[11]
(c) Hernandez-Galan, R. J.; Salva, R.; Massannet, G. M.; Collado, I. G. Tetrahedro. 1993, 49, 1701.
[12]
Atul, G.; Vishnu, J. R. Tetrahedro. 2009, 65, 7865.
[13]
Xu, M. M.; Cai, Q. Chin. J. Org. Chem. 2022, 42, 698 (in Chinese).
[13]
(徐萌萌, 蔡泉, 有机化学. 2022, 42, 698.)
[14]
(a) Benetti, S.; Romagnoli, R.; De Risi, C.; Spalluto, G.; Zanirato, V. Chem. Rev. 1995, 95, 1065.
[14]
(b) Bonne, D.; Coquerel, Y.; Constantieux, T.; Rodriguez, J. Tetrahedron: Asymmetr. 2010, 21, 1085.
[14]
(c) del Duque, M. M. S.; Allais, C.; Isambert, N.; Constantieux, T.; Rodriguez, J. In Synthesis of Heterocycles via Multicomponent Reactions I, Eds.: Orru, R. V. A.; Ruijter, E.,Springer Berlin Heidelberg, 2010, p. 227.
[14]
(d) Liang, Y. J.; Huang, P.; Zhang, R.; Dong, D. W. Chin. J. Org. Chem. 2014, 34, 1037 (in Chinese).
[14]
(梁永久, 黄鹏, 张睿, 董德文, 有机化学. 2014, 34, 1037.)
[15]
(a) Zhang Z. Ph.D. Dissertation. Northeast Normal University, Changchun, 2010 (in Chinese).
[15]
(张志国, 博士论文,东北师范大学, 长春, 2010.)
[15]
(b) Xiang, D.; Wang, K.; Liang, Y.; Zhou, G.; Dong, D. Org. Lett. 2008, 10, 345.
[15]
(c) Zhang, Z.; Zhang, Q.; Sun, S.; Xiong, T.; Liu, Q. Angew. Chem.. Int. Ed. 2007, 46, 1726.
[15]
(d) Wang, K.; Xiang, D.; Liu, J.; Pan, W.; Dong, D. Org. Lett. 2008, 10, 1691.
[15]
(e) Zhang, R.; Liang, Y.; Zhou, G.; Wang, K.; Dong, D. J. Org. Chem. 2008, 73, 8089.
[15]
(f) Xiang, D.; Yang, Y.; Zhang, R.; Liang, Y.; Pan, W.; Huang, J.; Dong, D. J. Org. Chem. 2007, 72, 8593.
[15]
(g) Zhang, R.; Zhang, D.; Guo, Y.; Zhou, G.; Jiang, Z.; Dong, D. J. Org. Chem. 2008, 73, 9504.
[15]
(h) Zhang, R.; Zhang, D.; Liang, Y.; Zhou, G.; Dong, D. J. Org. Chem. 2011, 76, 2880.
[16]
(a) Gao, B. C.; Sun, Y. F.; Wang, J.; Zu, L. W.; Zhang, X.; Liu, W. B. J. Heterocycl. Chem. 2018, 55, 2732.
[16]
(b) Gao, B. C.; Sun, Y. F.; Wang, J.; Chang, C.; Yuan, Z. G.; Tian, Y.; Shi, Y.Liu. W. B. J. Heterocycl. Chem. 2019, 56, 2281.
[16]
(c) Gao, B. C.; Sun Y. F. Wang, J.; Yuan, Z. G.; Zu, L. W.; Zhang, X.; Liu, W. B. RSC Adv. 2018, 8, 33625.
[16]
(d) Peter, Z.; Cheuk, K. L. Synlet. 2003, 215.
[16]
(e) Atul, G.; Fateh, V. S.; Ashoke, S.; Prakas, R. M. Synlett. 2005, 623.
[16]
(f) Vishnu, K. T.; Hardesh, K. M.; Balendu, K.; Brijesh, K.; Vishnu, J. R. Synlet. 2009, 2992.
[17]
Zhou, Q. F.; Zhao, S.; Wang, X.; Lu, T. Chin. J. Org. Chem. 2010, 30, 1652 (in Chinese).
[17]
(周庆发, 赵慎, 王珣, 陆涛, 有机化学. 2010, 30, 1652.)
[18]
(a) Wang, D. P.; Zhang, X. D.; Liang, Y.; Li, J. H. Chin. J. Org. Chem. 2006, 26, 19 (in Chinese).
[18]
(王德平, 张旭东, 梁云, 李金恒, 有机化学. 2006, 26, 19.)
[18]
(b) Lee, J. H.; Kim, W. S.; Lee, Y. Y.; Cho, C. G. Tetrahedron Lett. 2002, 43, 5779.
[18]
(c) Kim, W. S.; Kim, H. J.; Cho, C. G. J. Am. Chem. Soc. 2003, 125, 14288.
[19]
(a) Wang, Y. F.; Deng, W.; Liu, L.; Guo, Q. X. Chin. J. Org. Chem. 2005, 25, 8 (in Chinese).
[19]
(王晔峰, 邓伟, 刘磊, 郭庆祥, 有机化学. 2005, 25, 8.)
[19]
(b) Jin, X. Y.; Xiao, Q.; Ju, Y. Chin. J. Org. Chem. 2009, 29, 44 (in Chinese).
[19]
(靳玄烨, 肖强, 巨勇, 有机化学. 2009, 29, 44.)
[19]
(c) Fairlamb, I. J. S.; Lee, A. F.; Loe-Mie, F. E. M.; Niemel?, E. H.; O'Brien, C. T.; Whitwood, A. C. Tetrahedro. 2005, 61, 9827.
[19]
(d) Fairlamb, I. J. S.; O'Brien, C. T.; Lin, Z.; Lam, K. C. Org. Biomol. Chem. 2006, 4, 1213.
[20]
(a) Cerezo, S.; Moreno-Maňas, M.; Pleixats, R. Tetrahedro. 1998, 54, 7813.
[20]
(b) Afarinkia, K.; Berna-Canovas, J. Tetrahedron Lett. 2000, 41, 4955.
[21]
(a) Mochida, S.; Hirano, K.; Satoh, T.; Miura, M. J. Org. Chem. 2009, 74, 6295.
[21]
(b) Luo, T.; Schreiber, S. L. Angew. Chem.. Int. Ed. 2007, 46, 8250.
[22]
(a) Zhu, X. F.; Henry, C. E.; Wang, J.; Dudding, T.; Kwon, O. Org. Lett. 2005, 7, 1387.
[22]
(b) Dudding, T.; Kwon, O.; Mercier, E. Org. Lett. 2006, 8, 3643.
[22]
(c) Usachev, B. I.; Obydennov, D. L.; R?schenthaler, G. V.; Sosnovskikh, V. Y. Org. Lett. 2008, 10, 2857.
文章导航

/