A variety of substituted enamine derivatives were first found to be conveniently converted to the corresponding 2H-azirines mediated by phenyliodine (III) diacetate (PIDA). The formed 2-aryl-2H-azirines could be applied in the synthesis of indole-3-carbonitriles or isoxazoles via thermal rearrangements.

A variety of 3-functionalized benzo[b]furans were achieved by way of a FeCl(3)-mediated intramolecular cyclization of electron-rich alpha-aryl ketones. The alkoxy substituent on the benzene ring in the substrates was essential for an efficient cyclization to occur. This novel method allows the construction of benzo[b]furan rings by joining the O-atom on the side chain to the benzene ring via direct oxidative aromatic C-O bond formation.

Aziridine derivatives R 0040Simple Conversion of Enamines to 2H-Azirines and Their Rearrangements under Thermal Conditions. -A wide range of β-enaminonitriles is subjected to the aziridination reaction using PhI(OAc)2 as oxidant. The products easily rearrange thermally to afford indole derivatives. When an ester group is present instead of -CN [cf. (XIII)], the reaction is sensitive to electronic effects. Aziridines (XVI) bearing a carbonyl moiety lead to isoxazoles (XVII) instead of the expected indoles. -(LI, X.; DU*, Y.; LIANG, Z.; LI, X.; PAN, Y.; ZHAO*, K.; Org.

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