Abstract
Refluxing of 1,2-diaryl-1,1a-dihydroazirino[1,2-a]quinoxaline in 1-propanol leads to 3-aryl-1-arylmethyl-2-propoxy-1,2-dihydroquinoxalines or to aryl(3-aryl-1-arylmethyl-1,2-dihydroquinoxalin-2-yl) (3-aryl-2-hydroxy-1,2-dihydroquinoxalin-1-yl)methanes. Both processes are due to opening of the C-C bond of the aziridine ring; however, in the first process the ylids formed react with solvent molecules, whereas in the second process dimerization of the ylids with the participation of the water present in the solvent is observed.
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V. D. Orlov, F. G. Yaremenko, N. V. Lishtvan, and Yu. N. Surov, Khim. Geterotsikl. Soedin., No. 12, 1641 (1981).
H. W. Heine and R. P. Henzel, J. Org. Chem., 34, 171 (1969).
V. D. Orlov, F. G. Yaremenko, N. N. Kolos, N. S. Pivnenko, and V. F. Lavrushin, Khim. Geterotsikl. Soedin., No. 4, 544 (1980).
T. Do Minh and A. M. Trozzolo, J. Am. Chem. Soc., 92, 6997 (1970).
T. Do Minh and A. M. Trozzolo, J. Am. Chem. Soc., 94, 4046 (1972).
V. D. Orlov, F. G. Yaremenko, N. N. Kolos, and V. F. Lavrushin, Dokl. Akad. Nauk Ukr. SSR, Ser. B, No. 3, 247 (1978).
N. A. Leonard, K. Jann, J. V. Paukstelis, and C. K. Steinhard, J. Org. Chem., 28, 1499 (1963).
J. A. Barltrop, C. G. Richards, D. M. Russell, and G. Ryback, J. Chem. Soc., No. 3, 1132 (1959).
S. Bodforss, Ann. Chem., 633, 67 (1960).
J. Figueras, J. Org. Chem., 31, 803 (1968).
F. G. Yaremenko, V. D. Orlov, N. N. Kolos, and V. F. Lavrushin, Izv. Vyssh. Uchebn. Zaved., Khim. Khim. Tekhnol., 23, 831 (1980).
J. H. Beynon, Mass Spectrometry and Its Applications to Organic Chemistry, Elsevier, Amsterdam (1960).
E. P. Goldberg and H. R. Nace, J. Am. Chem. Soc., 77., 359 (1955).
I. Heilbron and H. M. Bunbury (editors), Dictionary of Organic Compounds, Vol. 3, Eyre and Spottiswoode, London (1953).
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See [1] for communication 6.
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 673–679, May, 1984.
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Orlov, V.D., Yaremenko, F.G., Tlakhun, M. et al. Aziridinyl ketones and their cyclic anils. 7. Solvolysis of 1,2-diaryl-1,1a-dihydroazirino[1,2-a]-quinoxalines. Chem Heterocycl Compd 20, 542–548 (1984). https://doi.org/10.1007/BF00514309
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DOI: https://doi.org/10.1007/BF00514309