Naphthofuran-4,9-dione derivatives exhibit a broad spectrum of biological and medicinal activities. The development of green and efficient methods for the synthesis of these heterocyclic compounds is of great importance. In this paper, the N-chloro-succinimide (NCS)-promoted reaction of 2-amino-benzo[g]chromene-3-carbonitriles or ethyl 2-amino-pyrano[3,2-c]-chromene-3-carboxylates with alcohols lead to the naphthofuran-4,9-dione or diethyl furo[3,2-c]chromene-2,2-dicarboxylate was reported. All reactions were completed in 30 min under room temperature, and two types of novel fused furan derivatives were obtained in 48%~97% yields under tandem ring-opening/cyclization processes.
Wang Xiang
,
Chen Ping
,
Zhi Sanjun
,
Hu Huayou
,
Kan Yuhe
,
Zhang Zaichao
. N-Chloro-succinimide-Promoted Efficient Synthesis of Naphthofuran-4,9-dione Derivatives[J]. Chinese Journal of Organic Chemistry, 2020
, 40(8)
: 2526
-2530
.
DOI: 10.6023/cjoc202004004
[1] Takegami, T.; Simamura, E.; Hirai, K. I.; Koyama, J. Antiviral Res. 1998, 37, 37.
[2] Inoue, K.; Inouye, H.; Chen, C. C. Phytochemistry 1981, 20, 2271.
[3] Heltzel, C. E.; Gunatilaka, A. A. L.; Glass, T. E.; Kingston, D. G. J. Nat. Prod. 1993, 56, 1500.
[4] Kobayashi, K.; Shimizu, H.; Sasaki, A.; Suginome, H. J. Org. Chem. 1993, 58, 4614.
[5] Lee, Y. R.; Kim, B. S.; Kim, D. H. Tetrahedron 2000, 56, 8845.
[6] Rad-Moghadam, K.; Hassani, S. A. R. M.; Roudsari, S. T. RSC Adv. 2016, 6, 13152.
[7] Liu, Y.; Ge, W.-H.; Zhu, Y.-Q.; Hu, H.-Y.; Fan, H.; Shi, Y.-H.; Wu, H. Eur. J. Org. Chem.; 2017, 551.
[8] Jiménez-Alonso, S.; Guasch, J.; Estévez-Braun, A.; Ratera, I.; Veciana, J.; Ravelo, A. G. J. Org. Chem. 2011, 76, 1634.
[9] Prasanna, P.; Balamurugan, K.; Perumal, S.; Menéndez, J. C. Green Chem. 2011, 13, 2123.
[10] Jiang, B.; Li, C.; Tu, S.-J.; Shi, F. J. Comb. Chem. 2010, 12, 482.
[11] Chennapuram, M.; Emmadi, N. R.; Bingi, C.; Nanubolu, J. B.; Atmakur, K. Green Chem. 2014, 16, 3237.
[12] Kale, A.; Chennapuram, M.; Bingi, C.; Nanubolu, J. B.; Atmakur, K. Org. Biomol. Chem. 2016, 14, 582.
[13] Kale, A.; Bingi, C.; Sripada, S.; Kumar, C. G.; Atmakur, K. Bioorg. Med. Chem. Lett. 2016, 26, 4899.
[14] Huang, X.; Liu, J. Chin. J. Org. Chem. 2018, 38, 1233(in Chinese). (黄新炜, 刘建利, 有机化学, 2018, 38, 3123.)
[15] Dekamin, M. G.; Eslami, M.; Maleki, A. Tetrahedron 2013, 69, 1074.
[16] Wang, X.; Chen, P.; Zhi, S.; Hu, H.; Kan, Y.; Zhang, Z. Chin. J. Org. Chem. 2019, 39, 3299(in Chinese). (王翔, 陈平, 支三军, 胡华友, 阚玉和, 张载超, 有机化学, 2019, 39, 3299.)
