Fischer cyclisation of phenylhydrazones of 1,3-disubstituted 4-piperidones leads, in general, to both tetrahydropyrimido[3,4-a]indoles and 3-substituted 2-(2-alkylaminoethyl)indoles (isotryptamines). The latter can also be synthesised in low yield from 3-substituted 2-methylindoles by the Mannich reaction. They are cyclised to tetrahydropyrimido[3,4-a]indoles by treatment with aldehydes.
C. J. Cattanach, A. Cohen and B. Heath-Brown, J. Chem. Soc. C, 1971, 359 DOI: 10.1039/J39710000359
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