The Ritter cyclocondensation of 2-methyl-1-phenylpropan-2-ols with cyanoacetohydrazide hydrazones in PhMe–H2SO4 medium at 60–70°С for 20 min resulted in the formation of N-benzylidene- and N-alkylidene(3,3-dialkyl-3,4-dihydroisoquinolin-1(2H)-ylidene)-acetohydrazides. The product of β-C-carbamoylation of the enamine moiety was also obtained.
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(а) Bolsakova, J.; Jirgensons, A. Chem. Heterocycl. Compd. 2017, 53, 1167. [Khim. Geterotsikl. Soedin.2017, 53, 1167.] (b) Khusnutdinov, R. I.; Egorova, T. M.; Meshcheryakova, E. S.; Khalilov, L. M.; Dzhemilev, U. M. Mendeleev Commun. 2019, 29, 143.
Anikina, L. V.; Vikharev, Yu. B.; Safin, V. A.; Gorbunov, A. A. ; Shklyaev, Yu. V.; Karmanov, V. I. Pharm. Chem. J.2002, 36(2), 18. [Khim.-farm. Zh.2002, 36(2), 19.]
Mikhailovskii, A. G.; Dolzhenko, A. V.; Syropyatov, B. Ya.; Shklyaev, Yu. V.; Vakhrin, M. I. Pharm. Chem. J.2002, 36, 288. [Khim.-farm. Zh.2002, 36(6), 8.]
Mikhailovskii, A. G.; Syropyatov, B. Ya.; Dolzhenko, A. V.; Vakhrin, M. I. Pharm. Chem. J.2002, 36, 374. [Khim.-farm. Zh.2002, 36(7), 33.]
Glushkov, V. A.; Anikina, L. V.; Vikharev, Yu. B.; Feshina, E. V.; Shklyaev, Yu. V. Pharm. Chem. J.2005, 39, 533. [Khim.-farm. Zh.2005, 39(10), 27.]
Vikharev, Yu. B.; Shklyaev, Yu. V. ; Anikina, L. V.; Kolla, V. E.; Tolstikov, A. G. Pharm. Chem. J.2005, 39, 405. [Khim.- farm. Zh.2005, 39(8), 13.]
Mikhailovskii, A. G.; Polygalova, N. N.; Ismailova, N. G.; Syropyatov, B. Ya.; Vakhrin, M. I. Pharm. Chem. J.2008, 42, 177. [Khim.-farm. Zh.2008, 42(4), 21.]
Limanskii, E. S.; Mikhailovskii, A. G.; Syropyatov, B. Ya.; Vakhrin, M. I. Pharm. Chem. J.2009, 43, 4. [Khim.-farm. Zh.2009, 43(1), 5.]
Limanskii, E. S.; Polygalova, N. N.; Syropyatov, B. Ya.; Mikhailovskii, A. G.;Vakhrin, M. I. Pharm. Chem. J.2009, 43, 89. [Khim.-farm. Zh.2009, 43(2), 20.]
Surikova, O. V.; Mikhailovskii, A. G.; Odegova, T. F. Pharm. Chem. J.2015, 48, 711. [Khim.-farm. Zh.2014, 48(11), 15.]
Surikova, O. V.; Mikhailovskii, A. G.; Syropyatov, B. Ya.; Yusov, A. S. Pharm. Chem. J.2016, 50, 794. [Khim.-farm. Zh.2016, 50(12), 22.]
Aksenov, N. A.; Maljuga, V. V.; Abakarov, G. M.; Aksenov, D. A.; Voskresenskii, L. G.; Aksenov, A. V. Russ. Chem. Bull., Int. Ed. 2019, 68, 1047. [ Izv. Akad. Nauk, Ser. Khim.2019, 1047.]
Surikova, O. V.; Yusov, A. S.; Mahmudov, R. R.; Mikhailovskii, A. G. Pharm. Chem. J.2017, 51, 18. [Khim.- farm. Zh.2017, 51(1), 20.]
Mikhailovskii, A. G.; Gashkova, O. V.; Rudakova, I. P.; Chashina, S. V.; Yusov, A. S. Pharm. Chem. J.2018, 52, 400. [Khim.-farm. Zh.2018, 52(5), 18.]
Mikhailovskii, A. G.; Yusov, A. S.; Mahmudov, R. R.; Starkova, A. V.; Rudakova, I. P. Pharm. Chem. J.2018, 52, 716. [Khim.-farm. Zh.2018, 52(8), 36.]
Yusov, A. S.; Chashina, S. V.; Mikhailovskii, A. G.; Rudakova, I. P. Pharm. Chem. J.2019, 53, 35. [Khim.-farm. Zh.2019, 53(1), 36.]
Kitaev, Yu. P.; Buzykin, B. I. Hydrazones [in Russian]; Moscow: Nauka, 1974, p. 381.
Mashkovskii, M. D. Drugs [in Russian]; Moscow: Novaya Volna, 2012.
Mikhailovskii, A. G.; Korchagin, D. V.; Yusov, A. S.; Gashkova, O. V. Chem. Heterocycl. Compd. 2017, 53, 1114. [Khim. Geterotsikl. Soedin.2017, 53, 1114.]
Zelenin, K. N.; Oleinik, S. V.; Alekseev, V. V.; Potekhin, A. A. Russ. J. Gen. Chem.2001, 71, 1116. [Zh. Obshch. Khim.2001, 71, 1182.]
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2020, 56(5), 562–565
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Mikhailovskii, A.G., Pogorelova, E.S. & Pershina, N.N. Synthesis of N-benzylidene- and N-alkylidene(3,3-dialkyl-3,4-dihydroisoquinolin-1(2H)-ylidene)acetohydrazides via the Ritter reaction. Chem Heterocycl Comp 56, 562–565 (2020). https://doi.org/10.1007/s10593-020-02700-w
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DOI: https://doi.org/10.1007/s10593-020-02700-w