Chemistry Letters

STUDIES ON QUINONES. VI. ACID-CATALIZED REARRANGEMENTS IN SOME 4-ACETYL-2, 3-DIHYDROBENZO [b] FURANS

L Barrios, VM Ruiz, R Tapia, J Valderrama, JC Vega

Index: Barrios, Luis; Ruiz, V. Manuel; Tapia, Ricardo; Valderrama, Jaime; Vega, Juan C. Chemistry Letters, 1980 , p. 187 - 190

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Citation Number: 5

Abstract

The reaction of 2-acetyl-and 5-acetyl-2-methoxy-1, 4-benzoquinone (1a, 1c) with N- propenylpiperidine gave the corresponding 2, 3-dihydrobenzo [b] furans, 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-dihydrobenzo [b] furan (2e).