Open image in new window
Hetaryl-substituted bicyclo[1.1.1]pentanes (microreview)
Article
First Online:
- 68 Downloads
Open image in new window Synthesis and properties of heterocycles bearing bicyclo[1.1.1]pentane moiety attached to the heterocyclic ring are summarized in this microreview. In particular, heterocyclizations with bicyclo-[1.1.1]pentane derivatives, as well as reactions involving incorporation of the preexisting heterocyclic system into the bicyclo[1.1.1]pentane core are discussed.
Notes
The funding of this work by Enamine Ltd. is acknowledged. Oleksandr O. Grygorenko was also funded by the Ministry of Education and Science of Ukraine (grant No. 19BF037-03). The authors thank Prof. Andrey A. Tolmachev for his encouragement and support.
References
- 1.Mykhailiuk, P. K. Org. Biomol. Chem.2019, 17, 2839.CrossRefGoogle Scholar
- 2.Kanazawa, J.; Uchiyama, M. Synlett2019, 1.Google Scholar
- 3.Adcock, W.; Binmore, G. T.; Krstic, A. R.; Walton, J. C.; Wilkie, J. J. Am. Chem. Soc.1995, 117, 2758.CrossRefGoogle Scholar
- 4.Costantino, G.; Maltoni, K.; Marinozzi, M.; Camaioni, E.; Prezeau, L.; Pin, J.-P.; Pellicciari, R. Bioorg. Med. Chem.2001, 9, 221.CrossRefGoogle Scholar
- 5.Stepan, A. F.; Subramanyam, C.; Efremov, I. V; Dutra, J. K.; O'Sullivan, T. J.; DiRico, K. J.; McDonald, W. S.; Won, A.; Dorff, P. H.; Nolan, C. E.; Becker, S. L.; Pustilnik, L. R.; Riddell, D. R.; Kauffman, G. W.; Kormos, B. L.; Zhang, L.; Lu, Y.; Capetta, S. H.; Green, M. E.; Karki, K.; Sibley, E.; Atchison, K. P.; Hallgren, A. J.; Oborski, C. E.; Robshaw, A. E.; Sneed, B.; O'Donnell, C. J. J. Med. Chem.2012, 55, 3414.CrossRefGoogle Scholar
- 6.Gao, X.; Wang, J.; Liu, J.; Guiadeen, D.; Krikorian, A.; Boga, S. B.; Alhassan, A.-B.; Selyutin, O.; Yu, W.; Yu, Y.; Anand, R.; Liu, S.; Yang, C.; Wu, H.; Cai, J.; Cooper, A.; Zhu, H.; Maloney, K.; Gao, Y.-D.; Fischmann, T. O.; Presland, J.; Mansueto, M.; Xu, Z.; Leccese, E.; Zhang-Hoover, J.; Knemeyer, I.; Garlisi, C. G.; Bays, N.; Stivers, P.; Brandish, P. E.; Hicks, A.; Kim, R.; Kozlowski, J. A. Bioorg. Med. Chem. Lett.2017, 27, 1471.CrossRefGoogle Scholar
- 7.Dron, P. I.; Zhao, K.; Kaleta, J.; Shen, Y.; Wen, J.; Shoemaker, R. K.; Rogers, C. T.; Michl, J. Adv. Funct. Mater.2016, 26, 5718.CrossRefGoogle Scholar
- 8.Kokhan, S. O.; Valter, Y. B.; Tymtsunik, A. V.; Komarov, I. V.; Grygorenko, O. O. Eur. J. Org. Chem.2017, 6450.CrossRefGoogle Scholar
- 9.Thirumoorthi, N. T.; Shen, C. J.; Adsool, V. A. Chem. Commun.2015, 51, 3139.CrossRefGoogle Scholar
- 10.Rehm, J. D. D.; Ziemer, B.; Szeimies, G. Eur. J. Org. Chem.1999, 1999, 2079.CrossRefGoogle Scholar
- 11.Messner, M.; Kozhushkov, S. I.; de Meijere, A. Eur. J. Org. Chem.2000, 1137.Google Scholar
- 12.Makarov, I. S.; Brocklehurst, C. E.; Karaghiosoff, K.; Koch, G.; Knochel, P. Angew. Chem., Int. Ed.2017, 56, 12774.CrossRefGoogle Scholar
- 13.Caputo, D. F. J.; Arroniz, C.; Dürr, A. B.; Mousseau, J. J.; Stepan, A. F.; Mansfield, S. J.; Anderson, E. A. Chem. Sci.2018, 9 , 5295.CrossRefGoogle Scholar
- 14.Thirumoorthi, N. T.; Adsool, V. A. Org. Biomol. Chem.2016, 14, 9485.CrossRefGoogle Scholar
- 15.Goh, Y. L.; Cui, Y. T.; Pendharkar, V.; Adsool, V. A. ACS Med. Chem. Lett.2017, 8, 516.CrossRefGoogle Scholar
- 16.Kanazawa, J.; Maeda, K.; Uchiyama, M. J. Am. Chem. Soc.2017, 139, 17791.CrossRefGoogle Scholar
Copyright information
© Springer Science+Business Media, LLC, part of Springer Nature 2019