Synthesis and application of azacycloalk-1-enefused oxazol-3-ium salts are summarized. The microreview covers all synthetic methods for obtaining 6,7-dihydro-5H-pyrrolo[2,1-b]oxazol-4-ium and 5,6,7,8-tetrahydrooxazolo[3,2-a]-pyridin-4-ium derivatives that have been classified in two distinct categories: cyclization leading to the formation of azacycloalk-1-ene ring and cyclization leading to the formation of oxazole ring. Application of these azacycloalk-1-enefused oxazol-3-ium salts has been discussed.
Similar content being viewed by others
References
(a) Tanner, M. E. Nat. Prod. Rep. 2015, 32, 88. (b) Ishikura, M.; Abe, T.; Choshi, T.; Hibino, S. Nat. Prod. Rep. 2015, 32, 1389. (c) Brandi, A.; Cicchi, S.; Cordero, F. M. Chem. Rev. 2008, 108, 3988. (d) Xu, J. X. Tetrahedron 2012, 68, 10696. (e) Jiao, L.; Liang, Y.; Xu, J. X. J. Am. Chem. Soc. 2006, 128, 6060. (f) Liang, Y.; Jiao, L.; Zhang, S. W.; Yu, Z. X.; Xu, J. X. J. Am. Chem. Soc. 2009, 131, 1542. (g) Qi, H. Z.; Li, X. Y.; Xu, J. X. Org. Biomol. Chem. 2011, 9, 2702. (h) Yang, Z. H.; Xu, J. X. J. Org. Chem. 2014, 79, 10703. (i) Yang, Z. H.; Chen, N.; Xu, J. X. J. Org. Chem. 2015, 80, 3611. (j) Xu, C. C.; Xu, J. X. J. Org. Chem. 2018, 83, 14733. (k) Fu, Z. C.; Sun, S. M.; Yang, A. J.; Sun, F.; Xu, J. X. Chem. Commun. 2019, 55, 13124. (l) Luo, Y.; Xu, J. X. Org. Lett. 2020, 22, 7780.
(a) Babaev, E. V.; Koval, Y. I.; Rybakov, V. B. Mendeleev Commun. 2020, 30, 228. (b) Babaev, E. V.; Rybakov, V. B. Molecules 2020, 25, 1682. (c) Shaikh, A. C.; Varma, M. E.; Mule, R. D.; Banerjee, S.; Kulkarni, P. P.; Patil, N. T. J. Org. Chem. 2019, 84, 1766. (d) Babaev, E. V.; Nevskaya, A. A.; Dlynnikh, I. V. Chem. Heterocycl. Compd. 2015, 51, 269. [Khim. Geterotsikl. Soedin. 2015, 51, 269.] (e) Babaev, E. V.; Alifanov, V. L.; Efimov, A. V. Russ. Chem. Bull., Int. Ed. 2008, 57, 845. [Izv. Akad. Nauk, Ser. Khim. 2008, 831.] (f) Babaev, E. V. Rev. J. Chem. 2011, 1, 161. [Obzorn. Zh. Khim. 2011, 1, 168.]
(a) Hom, M. E.; Ondrus, A. E.; Sakata-Kato, T.; Rack, P. G.; Chen, J. K. ChemMedChem 2020, 15, 1044. (b) Snyder, H. R., Jr.; Benjamin, L. E. J. Med. Chem. 1970, 13, 164.
Vedejs, E.; Piotrowski, D. W. J. Org. Chem. 1993, 58, 1341.
Vedejs, E.; Naidu, B. N.; Klapars, A.; Warner, D. L.; Li, V.-S.; Na, Y. H.; Kohn, H. J. Am. Chem. Soc. 2003, 125, 15796.
(a) Robinson, R. J. Chem. Soc. 1909, 95, 2167. (b) Gabriel, S. Ber. Dtsch. Chem. Ges. 1910, 43, 134.
(a) Zhang, J.; Fu, J.; Su, X.; Qin, X.; Zhao, M.; Shi, M. Chem. Commun. 2012, 48, 9625. (b) Shvaika, O. P.; Fomenko, V. I. J. Org. Chem. USSR 1974, 10, 2441. (c) Wang, J.; Gu, X.; Zhang, P.; Huang, X.; Zheng, X.; Chen, M.; Feng, H.; Kwok, R. T. K.; Lam, J. W. Y.; Tang, B. Z. J. Am. Chem. Soc. 2017, 139, 16974. (d) Sych, E. D.; Moreiko, O. V. Chem. Heterocycl. Compd. 1970, 6, 961. [Khim. Geterotsikl. Soedin. 1970, 1034.]
(a) Fujii, T.; Shigeyuki, Y.; Koichiro, Y. Chem. Pharm. Bull. 1978, 26, 2071. (b) Srairi, D.; Maurey, G. Bull. Soc. Chim. Fr. 1987, 297. (c) Malmusi, L.; Franchini, S.; Mucci, A.; Angeli, P.; Gulini, U.; Marucci, G.; Brasili, L. Med. Chem. Res. 1998, 8, 499.
Fujii, T.; Ohba, M.; Tachinami, T.; Miyajima, H.; Koch, M.; Seguin, E. Heterocycles 1986, 24, 1215.
Fujii, T.; Ohba, M.; Tachinami, T.; Miyajima, H. Chem. Pharm. Bull. 1990, 38, 1200.
Fujii, T.; Ohba, M.; Tachinami, T.; Ohashi, T.; Koch, M.; Seguin, E. Heterocycles 1989, 29, 1037.
Ohba, M.; Ohashi, T.; Fujii, T. Heterocycles 1991, 32, 319.
Fujii, T.; Ohba, M.; Shigeki, S. Chem. Pharm. Bull. 1995, 43, 49.
Paegle, E.; Belyakov, S.; Kirsch, G.; Arsenyan, P. Tetrahedron Lett. 2015, 56, 4554.
Financial support by the National Natural Science Foundation of China (No. 21911530099) and Russian Foundation for Basic Research (No. 19-53-53009 GFEN_a) are gratefully acknowledged.
Author information
Authors and Affiliations
Corresponding author
Additional information
Published in Khimiya Geterotsiklicheskikh Soedinenii, 2021, 57(1), 10–12
Rights and permissions
About this article
Cite this article
Xu, J., Babaev, E.V. Synthesis and application of azacycloalk-1-ene-fused oxazol-3-ium salts (microreview). Chem Heterocycl Comp 57, 10–12 (2021). https://doi.org/10.1007/s10593-021-02860-3
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10593-021-02860-3