Abstract
Some factors affecting the formation of tryptamtnes from arylhydrazines and halogenocarbonyl compounds have been studied. It has been shown by calculations using the LCAO MO method that the Β-nitrogen atom of the arylhydrazone must undergo intramolecular quaternization, and the formation of a C-C bond takes place by electrophilic attack of the benzene ring. It has been shown that conformational factors play an important part in the reaction, sometimes changing the direction of the process. Thus, γ-chloropropyl phenyl ketone, which exists only in the syn form, cyclizes into 1,3-diphenyltetrahydropyridazine and not into 2-phenyltryptamine.
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For Communication VII, see [1].
Translated from Khimiya Geterotsiklicheskikh Soedinenii, Vol. 6, No. 6, pp. 750–755, June, 1970.
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Grandberg, I.I., Zuyanova, T.I., Przheval'skii, N.M. et al. Indoles. Chem Heterocycl Compd 6, 693–697 (1970). https://doi.org/10.1007/BF00470519
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DOI: https://doi.org/10.1007/BF00470519