Abstract
Dimethyl acetylenedicarboxylate reacts with 4-substituted and 3,4-fused 2-furyl-1,2,3,4-tetrahydroquinoline derivatives at the furan fragment according to the [4 + 2]-cycloaddition pattern. The reaction is not stereoselective, and it yields two diastereoisomeric 7-oxabicyclo[2.2.1]hepta-2,5-dienes whose structure was determined by X-ray analysis and NMR spectroscopy.
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Dedicated to Full Member of the Russian Academy of Sciences V.A. Tartakovskii on his 75th Anniversary
Original Russian Text © F. I. Zubkov, V. P. Zaitsev, A. A. Orlova, A. S. Peregudov, N. M. Mikhailova, A. V. Varlamov, 2007, published in Zhurnal Organicheskoi Khimii, 2007, Vol. 43, No. 8, pp. 1201–1206.
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Zubkov, F.I., Zaitsev, V.P., Orlova, A.A. et al. Product structure in the reaction of dimethyl acetylenedicarboxylate with 2-furyl-1,2,3,4-tetrahydroquinolines. Russ J Org Chem 43, 1202–1208 (2007). https://doi.org/10.1134/S1070428007080209
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DOI: https://doi.org/10.1134/S1070428007080209