Photoaddition Reaction of Pyrroles and Indoles to N-Methyl-2-pyridone

概要

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Photoaddition reactions of pyrroles (2-4) and indoles (5-8) to N-methyl-2-pyridone (1) have been investigated. The reaction occurred primarily by way of addition of the C_2-H bond of the pyrrole ring and the C_3-H bond of the indole ring to the pyridone nucleus, yielding 4-substituted 3,4-dihydro-1-methylpyridin-2(1H)-ones (9 from pyrrole; 13 and 17 from indoles) and 6-substituted 3,6-dihydro-1-methylpyridin-2(1H)-ones (10 from pyrrole; 14 and 18 from indoles). The presence of a methyl group(s) at the reactive site(s) of pyrrole and indole resulted in the formation of the products arising from the addition of the C_3-H bond of the pyrrole ring, and the N_1-H, C_2-H and C_6-H bonds of the indole ring. N-Methylpyrrole (4) and N-methylindole (8) did not give any detectable amount of the addition product.
社団法人日本薬学会の論文
1992-04-25