Journal of Organic Chemistry p. 3665 - 3668 (1982)
Update date:2022-08-05
Topics:
Yuste, Francisco
Sanchez-Obregon, Ruben
The base-catalyzed reaction of hydroxy lactone 1 with several cyclic and acyclic vinylogous amides and 1,3-dicarbonyl compounds was found to provide a smooth method to prepare pyrrole, furan, tetrahydroindole, and tetrahydrobenzofuran ring systems.The reaction of 1 with the cyclic enaminone 2 affords 3 which can be isomerized to the tetrahydroindole-2-acetic acid 4.The reaction of 1 with 6 and 8 produces, after esterification, the methyl tetrahydroindole-and pyrrole-2-acetates 7a and 9a, respestively.With acyclic 1,3-dicarbonyl compounds, 1 reacts to give furan-2-acetic acids, whereas the reaction of 1 with cyclic β-diketones leads to furo<3,2-b>benzofuran derivatives.The latter can be easily isomerized by heating with diluted acid to the corresponding tetrahydrobenzofuran-2-acetic acids.A possible mechanism for these reactions is proposed.
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Doi:10.1016/S0008-6215(82)80027-X
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(1965)