Ring contraction reactions of methyl quinoline 1-oxide 5-carboxylates via the corresponding benz[d]-1,3-oxazepines. A facile synthesis of methyl indole 4-carboxylate and its derivatives.

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A new synthetic method of the 4-substituted indoles from 5-substituted quinoline 1-oxides was developed. The method involves a photochemical ring enlargement of the N-oxides to benz [d]-1, 3-oxazepines and subsequent ring contraction to these indoles under thermal or photochemical conditions. An interesting ring contraction of the 6-alkoxycarbonyl-2-cyanobenz [d]-1, 3-oxazepine to 5-aminoisocoumarins and their ring transformation to the 4-alkoxycarbonylindoles were also disclosed.

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