The N-oxime-substituted pyrazole-fused porphyrin derivatives were synthesized by the reaction of pyrazole-fused porphyrin with 2,6-dichlorobenzonitrile oxide in moderate yield. The structures of all the products were characterized by NMR, UV spectroscopy, HRMS together with X-ray crystallographic analysis.
Similar content being viewed by others
References
Cheng, Y.; Yang, G.; Jiang, H.; Zhao, S.; Liu, Q.; Xie, Y. ACS Appl. Mater. Interfaces 2018, 10, 38880.
Chang, K.; Tang, Y.; Fang, X.; Yin, S.; Xu, H.; Wu, C. Biomacromolecules 2016, 17, 2128.
(a) Cui, W.; Wayland, B. B. J. Am. Chem. Soc. 2004, 126, 8266. (b) Zhou, Z.; Zhou, X.; Liu, Q.; Zhang, X.; Liu, H. Org. Lett. 2015, 17, 4078.
Baldwin, J. E.; Crossley, M. J.; DeBernardis, J. Tetrahedron 1982, 38, 685.
(a) Crossley, M. J.; Harding, M. M.; Tansey, C. W. J. Org. Chem. 1994, 59, 4433. (b) Deng, Z.; Li, X.; Stępień, M.; Chmielewski, P. J. Chem.–Eur. J. 2016, 22, 4231.
(a) Tomé, A. C.; Lacerda, P. S. S.; Neves, M. G. P. M. S.; Cavaleiro, J. A. S. Chem. Commun. 1997, 1199. (b) Vicente, M. G. H.; Cancilla, M. T.; Lebrilla, C. B.; Smith, K. M. Chem. Commun. 1998, 2355. (c) Silva, A. M. G.; Tomé, A. C.; Neves, M. G. P. M. S.; Cavaleiro, J. A. S. Tetrahedron Lett. 2000, 41, 3065.
(a) Lacerda, P. S. S.; Silva, A. M. G.; Tomé, A. C.; Neves, M. G. P. M. S.; Silva, A. M. S; Cavaleiro, J. A. S.; Llamas-Saiz, A. L. Angew. Chem., Int. Ed. 2006, 45, 5487. (b) Yang, L.-L.; Li, X.-F.; Hu, X.-L.; Yu, X.-Y. Tetrahetron Lett. 2016, 57, 1265. (c) Silva, A. M. G.; Tomé, A. C.; Neves, M. G. P. M. S.; Silva, A. M. S.; Cavaleiro, J. A. S. J. Org. Chem. 2005, 70, 2306. (d) Li, X.; Zhuang, J.; Li, Y.; Liu, H.; Wang, S.; Zhu, D. Tetrahetron Lett. 2005, 46, 1555. (e) Li, X.; Liu, B.; Yu, X.; Yi, P.; Yi, R.; Chmielewski, P. J. J. Org. Chem. 2012, 77, 2431. (f) Fu, X.; Meng, Y.; Li, X.; Stępień, M.; Chmielewski, P. J. Chem. Commun. 2018, 54, 2510.
Yang, L.-L.; Hu, X.-L.; Tang, Z.-Q.; Li, X.-F. Chem. Lett. 2015, 44, 1515.
(a) Bonnett, R.; Nizhnik, A. N.; Berenbaum, M. C. J. Chem. Soc., Chem. Commun. 1989, 1822. (b) Brückner, C.; Dolphin, D. Tetrahedron Lett. 1995, 36, 3295. (c) Chang, C. K.; Sotiriou, C. J. Org. Chem. 1985, 50, 4989.
(a) Whitlock, H. W.; Hanauer, R.; Oester, M. Y.; Bower, B. K. J. Am. Chem. Soc. 1969, 91, 7485. (b) Liu, B.; Li, X.; Stępień, M.; Chmielewski, P. J. Chem.–Eur. J. 2015, 21, 7790. (c) Nozawa, R.; Yamamoto, K.; Hisaki, I.; Shin, J.-Y.; Shinokubo, H. Chem. Commun. 2016, 52, 7106. (d) Stolzenberg, A. M.; Simerly, S. W.; Steffey, B. D.; Haymond, G. S. J. Am. Chem. Soc. 1997, 119, 11843.
(a) Savage, G. P. Curr. Org. Chem., 2010, 14, 1478. (b) Efimov, I. V.; Shafran, Y. M.; Volkova, N. N.; Belyaev, N. A.; Slepukhin, P. A.; Bakulev, V. A. Chem. Heterocycl. Compd. 2016, 52, 743. [Khim. Geterotsikl. Soedin. 2016, 52, 743.] (c) Vafina, G. F.; Mukhamed'yanova, A. A.; Khanova, M. D.; Spirikhin, L. V. Chem. Heterocycl. Compd. 2018, 54, 796. [Khim. Geterotsikl. Soedin. 2018, 54, 796.] (d) Markitanov, Y. N.; Timoshenko, V. M.; Shermolovich, Y. G. Chem. Heterocycl. Compd. 2018, 54, 89. [Khim. Geterotsikl. Soedin. 2018, 54, 89.] (e) Prasad, S. S.; Baskaran, S. J. Org. Chem. 2018, 83, 1558. b Swapnaja, K. J. M.; Yennam, S.; Chavali, M. Tetrahetron Lett. 2019, 60, 461. c Li, F.; Hu, Y.; Wang, Y.; Ma, C.; Wang, J. J. Med. Chem. 2017, 60,1580.
(a) Grundmann, C.; Dean, J. M. J. Org. Chem., 1965, 30, 2809. (b) Li, X.; Zheng, A.; Liu, B.; Li, G.; Yu, X.; Yi, P. J. Heterocycl. Chem. 2011, 48, 776. (c) Li, X.; Zheng, A.; Liu, B.; Yu, X.; Yi, P. J. Heterocycl. Chem. 2013, 50, 1198. (d) Li, X.; Yi, R.; Liu, B.; Zheng, A.; Yu, X.; Yi, P. J. Heterocycl. Chem. 2014, 51, 274. (e) Li, X.; Zheng, A.; Liu, B.; Yu, X.; Yi, P. J. Heterocycl. Chem. 2010, 47, 1157. (f) Krompiec, S.; Penczek, R.; Bujak, P.; Kubik, E.; Malarz, J.; Penkala, M.; Krompiec, M.; Kuźnik, N.; Maciejewski, H. Tetrahedron Lett. 2009, 50, 1193.
(a) Ren, D.; Liu, B.; Li, X.; Koniarz, S.; Pawlicki, M.; Chmielewski, P. J. Org. Chem. Front. 2019, 6, 1066. (b) Liu, B.; Yoshida, T.; Li, X.; Stępień, M.; Shinokubo, H.; Chmielewski, P. J. Angew. Chem., Int. Ed., 2016, 55, 13142. (c) Li, X.; Meng, Y.; Yi, P.; Stępień, M.; Chmielewski, P. J. Angew. Chem., Int. Ed., 2017, 56, 10810. (d) Liu, B.; Fang, H.; Li, X.; Cai, W.; Bao, L.; Rudolf, M.; Plass, F.; Fan, L.; Lu, X.; Guldi, D. M. Chem.–Eur. J., 2015, 21, 746. (e) Liu, B.; Li, X.; Maciołek, J.; Stępień, M.; Chmielewski, P. J. J. Org. Chem. 2014, 79, 3129. (f) Liu, B.; Li, X.; Xu, X.; Stępień, M.; Chmielewski, P. J. J. Org. Chem. 2013, 78, 1354.
Sheldrick, G. M. SADABS; University of Göttingen: Göttingen, 1996.
SAINT software Reference Manual; Bruker AXS: Wisconsin, 1998.
Sheldrick, G. M. Acta Crystallogr., Sect. C: Struct. Chem. 2015, C71, 3.
We are grateful to the National Natural Science Foundation of China (No. 21671063) for the financial support.
Author information
Authors and Affiliations
Corresponding author
Additional information
Published in Khimiya Geterotsiklicheskikh Soedinenii, 2019, 55(7), 644–647
Rights and permissions
About this article
Cite this article
Hu, X., Huang, Y., Fu, X. et al. Synthesis of N-oxime-substituted pyrazole-fused porphyrin derivatives. Chem Heterocycl Comp 55, 644–647 (2019). https://doi.org/10.1007/s10593-019-02510-9
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10593-019-02510-9