A simple methodology was developed for the synthesis of 5,11-dialkyl-5,6,11,12-tetrahydro-6,12-epoxydibenzo[b,f][1,5]diazocines by treatment of the respective 2-alkylaminobenzaldehydes with hydrogen chloride solution in dioxane at room temperature.
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Vo, C.-V. T.; Bode, J. W. J. Org. Chem. 2014, 79, 2809.
Marson, C. M. In Heterocyclic Chemistry in the 21st Century: A Tribute to Alan Katrizky; Scriven, E. F. V.; Ramsden, H. C., Eds.; Academic Press, 2017, p. 13.
Dolenský, B.; Elguero, J.; Král, V.; Pardo, C.; Valík, M. Adv. Heterocycl. Chem. 2007, 93, 1.
Tröger, J. J. Prakt. Chem. 1887, 36, 225.
Veale, E. B.; Frimannsson, D. O.; Lawler, M.; Gunnlaugsson, T. Org. Lett. 2009, 11, 4040.
Veale, E. B.; Gunnlaugsson, T. J. Org. Chem. 2010, 75, 5513.
Tatibouët, A.; Demeunynck, M.; Andraud, C.; Collet, A.; Lhomme, J. Chem. Commun. 1999, 161.
Baldeyrou, B.; Tardy, C.; Bailly, C.; Colson, P.; Houssier, C.; Charmantray, F.; Demeunynck, M. Eur. J. Med. Chem. 2002, 37, 315.
Johnson, R. A.; Gorman, R. R.; Wnuk, R. J.; Crittenden, N. J.; Aiken, J. W. J. Med. Chem. 1993, 36, 3202.
Wang, Z.; Wang, D.; Zhang, F.; Jin, J. ACS Macro Lett. 2014, 3, 597.
Muthukrishnan, I.; Karuppasamy, M.; Nagarajan, S.; Maheswari, C. U.; Pace, V.; Menéndez, J. C.; Sridharan, V. J. Org. Chem. 2016, 81, 9687.
Chen, Y.; Li, S.; Hou, S.; Xu, J.; Yang, Z. J. Org. Chem. 2020, 85, 3709.
Michalak, M.; Bisek, B.; Nowacki, M.; Górecki, M. J. Org. Chem. 2021, 86, 8955.
Czerwiński, P.; Michalak, M. J. Org. Chem. 2017, 82, 7980.
Shidlovskii, A. F.; Golubev, A. S.; Gusev, D. V.; Suponitsky, K. Yu.; Peregudov, A. S.; Chkanikov, N. D. J. Fluorine Chem. 2012, 143, 272.
Gazvoda, M.; Krivec, M.; Časar, Z.; Košmrlj, J. J. Org. Chem. 2018, 83, 2486.
Wang, Y.; Ai, J.; Liu, G.; Geng, M.; Zhang, A. Org. Biomol. Chem. 2011, 9, 5930.
Albert, A.; Yamamoto, H. J. Chem. Soc. C 1968, 1944.
Apple, I. A.; Meth-Cohn, O. ARKIVOC 2002, (vi), 4.
Zhu, J.-K.; Gao, J.-M.; Yang, C.-J.; Shang, X.-F.; Zhao, Z.-M.; Lawoe, R. K.; Zhou, R.; Sun, Y.; Yin, X.-D.; Liu, Y.-Q. J. Agric. Food Chem. 2020, 68, 2306.
Ghandi, M.; Kia, M. A.; Sadeghzadegh, M.; Bozcheloei, A. H.; Kubicki, M. J. Heterocycl. Chem. 2015, 52, 1646.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2022, 58(6/7), 354–357
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Ivanov, D.S., Zaitseva, E.R., Smirnov, A.Y. et al. Synthesis of 5,11-dialkyl-5,6,11,12-tetrahydro-6,12-epoxydibenzo[b,f][1,5]diazocines from 2-alkylaminobenzaldehydes. Chem Heterocycl Comp 58, 354–357 (2022). https://doi.org/10.1007/s10593-022-03097-4
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DOI: https://doi.org/10.1007/s10593-022-03097-4