The alkylation of 4-methylquinolin-2(1Н)-one with methallyl chloride gave a regioisomer mixture containing 1-methallyl-4-methylquinolin-2(1Н)-one and 2-methallyloxy-4-methylquinoline, which reacted with iodine and bromine and formed dihydrooxazolo[3,2-а]- quinolinium systems.
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(a) Jiang, X.; Liu, H. In Comprehensive Organic Synthesis II; Knochel, P.; Molander, G. A., Eds.; Elsevier: Oxford, 2014, Vol. 4, p. 412. (b) Godoi, B.; Schumacher, R. F.; Zeni, G. Chem. Rev. 2011, 111, 2937.
(a) Gutsulyak, B. M. Russ. Chem. Rev. 1972, 41, 187. [Usp. Khim. 1972, 346.] (b) Bishnoi, A.; Tiwari, A. K.; Singh, S.; Sethi, A.; Tripathi, C. M.; Banerjee, B. Med. Chem. Res. 2013, 22, 3527.
Abd El-Aal, R. M. Proc. Indian Acad. Sci., Chem. Sci. 1999, 111, 343.
(a) Gyulbudagyan, L. V.; Aleksanyan, I. L.; Avetisyan, A. A. Armyanskiy Khim. Zhurn. 1989, 42, 636. (b) Ukrainets, I. V.; Bereznyakova, N. L.; Parshikov, V. A.; Turov, A. V. Chem. Heterocycl. Compd. 2007, 43, 1269. [Khim. Geterotsikl. Soedin. 2007, 1496.] (c) Kim, D. G.; Brisyuk, N. P.; Lykasova, E. A. Izv. Vuzov. Khimiya i Khim. Tekhnologiya 1991, 34, 120. b Ukrainets, I. V.; Sidorenko, L. V.; Gorokhova, O. V.; Shishkina, S. V.; Turov, A. V. Chem. Heterocycl. Compd. 2007, 43, 617. [Khim. Geterotsikl. Soedin. 2007, 736.]
Onysko, M. Yu.; Lendel, V. G. Chem. Heterocycl. Compd. 2007, 43, 1020. [Khim. Geterotsikl. Soedin. 2007, 1204.]
Vershinina, E. A.; Kim, D. G. Vestn. Yuzh. Ural. Gos. Universiteta., Ser. Khim. 2010, 31, 10.
Sheldrick, G. M. Acta Crystallogr., Sect. A: Found. Crystallogr. 2008, A64, 112.
This work was performed with financial support from the government of the Russian Federation (act No. 211 of March 16, 2013, contract No. 02.A03.21.0011) and within the framework of State contract (No. 4.9665.2017/8.9) on the equipment of the Collective Use Center “Spectroscopy and Analysis of Organic Compounds”.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2018, 54(10), 977–980
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Kim, D.G., Vershinina, E.A., Ovchinnikova, I.G. et al. Synthesis and halocyclization of 4-methylquinolin-2(1H)-one N- and O-methallyl derivatives. Chem Heterocycl Comp 54, 977–980 (2018). https://doi.org/10.1007/s10593-018-2374-z
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DOI: https://doi.org/10.1007/s10593-018-2374-z