Abstract
N-Sulfonyl derivatives of 1,4-benzoquinone imine reacted with enamines to give 1,4-addition products and products of their subsequent cyclization, substituted 5-aminobenzofurans and 5-aminoindoles, depending on the solvent nature, electron-withdrawing power of the substituent on the quinone imine nitrogen atom, and enamine structure. The presence of strong electron-withdrawing trifluoromethanesulfonyl group on the quinone imine nitrogen atom favors formation of 1,4-addition products and benzofuran derivatives.
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Original Russian Text © S.A. Konovalova, A.P. Avdeenko, V.V. Pirozhenko, A.L. Yusina, G.V. Palamarchuk, S.V. Shishkina, 2017, published in Zhurnal Organicheskoi Khimii, 2017, Vol. 53, No. 4, pp. 519–532.
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Konovalova, S.A., Avdeenko, A.P., Pirozhenko, V.V. et al. Reaction of N-sulfonyl-1,4-benzoquinone imines with enamines. Russ J Org Chem 53, 525–538 (2017). https://doi.org/10.1134/S1070428017040054
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DOI: https://doi.org/10.1134/S1070428017040054