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Several 3-substituted 2-azidomethylindoles have been synthesized in high yields either by the reaction of 3-substituted 2-alkylindoles with iodine azide in dry acetonitrile or by treatment of 3-substituted 2-alkyl-3-chloroindolenines with sodium azide in acetic acid. 1, 3-Dipolar cycloaddition of the 2-azidomethylindoles with dimethyl acetylenedicarboxylate gives 2-triazolylmethylindole derivatives. Ozonolysis of 3-phenyl-2-azidomethylindoles in acetic acid gives 2-azidoacetamidobenzophenones, which cyclize to 1, 4-benzodiazepines by treating with triphenylphosphine in toluene at room temperature and then refluxing.

1 H -1-Benzazepines were synthesized by thermal ring opening of 2a,7b-dihydrocyclobut[ b ]indoles. The thermal and photochemical behavior of the 1 H -1-benzazepines is also described.

The intermittent plasma-assisted vacuum deposition technique has been found to introduce the effective electrocatalytic activity and stability for CO 2 reduction into metal phthalocyanine thin films formed on a glassy carbon. The film properties are significantly influenced by the chemical state of the film. It is suggested that the electrode process is determined by the surface chemical reaction involving adsorbed H and/or H + and a carbon containing intermediate.

Reaction of 2-methyltryptophol (1a) with 1 molar equivalent of iodine azide gives 3a-azido-8a-methyl-3,3a,8,8a-tetrahydro-2H-furo[2,3-b]indole, which isomerises to 2-azidomethyltryptophol in acetic acid at room temperature. Similar treatment of Nα-acetyl-2-methyltryptamine affords two products, 1-acetyl-3a-azido-8a-methyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole and Nα-acetyl-2-azidomethyltryptamine; the former does not isomerise to the latter in acetic acid. Tryptophol and Nα-acetyltryptamine also give the corresponding 3a-azidofuro and -pyrrolo-indole derivatives in low yields.

The regio- and stereo-selectivities in the [2 + 2] photocycloaddition of a series of 1-benzoylindoles with vinyl acetate and methyl acrylate have been investigated. With some exceptions, the 1 -benzoylindoles gave exclusively or predominantly the corresponding 1-acetoxy-3-benzoyl and 3-benzoyl-1-methoxycarbonyl-1,2,2a,7b-tetrahydro-3H-cyclobut[b]indoles as mixtures of stereoisomers.

Syntheses and thermolyses of 3-substituted 2a,7b-dihydro-3H-cyclobut[b]indoles and some 2a-methyl derivatives are described. X-Ray crystal-structure analyses were carried out on the 3-acetyl and 3-pivaloyl derivatives, which both crystallise in the monoclinic system; space group C2/c, Z= 8, a= 15.277(7), b= 9.035(5), c= 14.485(11)A, β= 104.27(5)° for the former, and space group P21/c, Z= 4, a= 8.696(7), b= 15.227(12), c= 9.428(8)A, β= 102.67(7)° for the latter. The crystal structures were solved by direct methods, and atomic parameters refined to R= 0.118 (for the acetyl derivative) and R= 0.108 (for the pivaloyl derivative). No abnormal results were found. Direct thermolyses of the dihydrocyclobut[b]indoles resulted in the formation of 1-substituted 1H-1-benzazepines, N-substituted 1-naphthylamines, and 1-substituted indoles, whose relative distributions depend upon the nature of the substrate and the reaction temperature. The presence of silver ion significantly lowered the temperature necessary for ring opening and gave the 1H-1-benzazepines in variable yields. The 3-benzoyl-2a-methyl derivative, when heated in the presence of silver ion, gave both the rearrangement product 1-methyl dihydro-3H-cyclobut[b]indole and its ring-opened derivative, in addition to the 2-methyl-1H-1-benzazepine. The thermal and photochemical behaviour of these 1 H-1-benzazepines is also described.