Fujio Tabusa

Photo-isomerisation of 1-acetyl-2-cyano-1,2-dihydroquinolines to N-acetylbenzoazetines

1-Acetyl-2-cyano-1,2-dihydroquinolines isomerise photochemically to give N-acetylbenzoazetines, the formation of which is rationalised in terms of benzoazahexatriene intermediates.

Photochemical synthesis of 2,3-homoindoles

Irradiation of ethyl 2-cyano-4-methyl-1,2-di-hydroquinoline-1-carboxylates in ethanol gives stereospecifically ethyi endo-1-cyano-6b-methyl-1, 1a,2,6b-tetra-hydrocycloprop[b]indole-2-carboxylates(2,3-homoindoles) in 59–61% yields, which are shown to be useful synthetic intermediates for indole derivatives.

Photochemistry of ethyl 4-substituted 2-cyano-1,2-dihydroquinoline-1-carboxylates (Reissert compounds): syntheses of cycloprop[b]indoles

Irradiation of ethyl 4-subslituted 2-cyano-1,2-dihydroquinoline-1-carboxylates (Reissert compounds) in ethanol gives ethyl 6b-substituted 1-cyano-1,1a.2,6b-tetrahydrocycloprop[b]indole-2-carboxylates. The stereochemistry of the products has been determined by n.m.r. spectroscopy.