Chemistry Letters p. 187 - 190 (1980)
Update date:2022-07-29
Topics:
Barrios, Luis
Ruiz, V. Manuel
Tapia, Ricardo
Valderrama, Jaime
Vega, Juan C.
The reaction of 2-acetyl- and 5-acetyl-2-methoxy-1,4-benzoquinone (1a, 1c) with N-propenylpiperidine gave the corresponding 2,3-dihydrobenzofurans, 2b and 2c, containing the acetyl group at C-4.Acid treatment of these dihydrofurans rearranged to 8-methyl- and 2-methoxy-8-methyljuglone (4a, 4b).Juglone (4c) and 2,3-dihydrojuglone (6) were obtained in fair yields from 4-acetyl-2,5-dihydroxy-2,3-dihydrobenzofuran (2e).
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