Abstract
A new procedure has been proposed for the synthesis of previously unknown pyrrolo- and indolo-1,4-epoxy[1,4]oxazepines by epoxymethylation of 2-benzoyl-1H-pyrrole and 2-benzoyl-1H-indoles with epichlorohydrin. Some transformations of the epoxymethylation products have been studied.
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REFERENCES
Fauran, C.P., Eberle, J.A., Turin, M.J., Raynaud, G.M., and Gouret, C.J., US Patent no. 3951968, 1974.
Angelini, T., Fringuelli, F., Lanari, D., Pizzo, F., and Vaccaro, L., Tetrahedron Lett., 2010, vol. 51, p. 1566. https://doi.org/10.1016/j.tetlet.2010.01.055
Janeliunas, D., Daskeviciene, M., Malinauskas, T., and Getautis, V., Tetrahedron, 2009, vol. 65, p. 8407. https://doi.org/10.1016/j.tet.2009.07.093
MacMillan, K.S., Naidoo, J., Liang, J., Melito, L., Williams, N.S., Morlock, L., Huntington, P.J., Estill, S.J., Longgood, J., Becker, G.L., McKnight, S.L., Pieper, A.A., De Brabander, J.K., and Ready, J.M., J. Am. Chem. Soc., 2011, vol. 133, p. 1428. https://doi.org/10.1021/ja108211m
Kharaneko, A.O., Pekhtereva, T.M., and Kharaneko, O.I., Russ. J. Org. Chem., 2020, vol. 56, p. 95. https://doi.org/10.1134/S1070428020010169
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Kharaneko, A.O., Pekhtereva, T.M. & Kharaneko, O.I. Epoxymethylation of 2-Acyl-Substituted NH Heterocycles and Transformations of the Epoxymethylation Products. Russ J Org Chem 56, 1677–1684 (2020). https://doi.org/10.1134/S1070428020100012
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DOI: https://doi.org/10.1134/S1070428020100012
Keywords:
- epoxymethylation
- 1-phenyl-4,5-dihydro-1H,3H-1,4-epoxy[1,4]oxazepino[4,3-a]benzimidazole
- 7,8,9-trimethyl-1-phenyl-4,5-dihydro-1H,3H-1,4-epoxypyrrolo[2,1-c][1,4]oxazepine
- phenyl[3,4,5-trimethyl-1-(oxiran-2-ylmethyl)-1H-pyrrol-2-yl]methanone
- 11-methyl-1-phenyl-4,5-dihydro-1H,3H-1,4-epoxy[1,4]oxazepino[4,3-a]indole
- 6-methyl-9-(oxiran-2-ylmethyl)-2,3,4,9-tetrahydro-1H-carbazol-1-one
- 9-[2-hydroxy-3-(piperidin-1-yl)propyl]-2,3,4,9-tetrahydro-1H-carbazol-1-one