Abstract
The reaction of 1-(3,4-dimethoxy)phenylcycloalkanemethane- and 4-(3,4-dimethoxyphenyl)tetrahydropyran-4-methanamines with benzo[d][1,3]dioxol-5-carbonyl chloride was used to synthesize N-substituted benzo[d][1,3]dioxol-5-carboxamides. The cyclization of the latter with phosphorus oxychloride gave dihydroisoquinolines, whose subsequent reduction with sodium borohydride to spiro-substituted tetrahydroisoquinolines followed by Eschweiler–Clark reaction gave N-methyl derivatives. The condensation of the starting amines with benzo[d][1,3]dioxol-5-carbaldehyde formed Schiff bases, which were reduced with sodium borohydride to obtain the corresponding secondary amines―acyclic analogs of tetrahydroisoquinolines. The cyclization of the latter products under Eschweiler–Clark reaction resulted in the synthesis of N-benzodioxolmethyl-substituted tetrahydroisoquinolines.
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Translated from Zhurnal Organicheskoi Khimii, 2023, Vol. 59, No. 11, pp. 1446–1454 https://doi.org/10.31857/S051474922311006X.
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Arustamyan, Z.S., Margaryan, R.E., Aghekyan, A.A. et al. Synthesis and Antiarrhythmic Activity of New Benzodioxol- substituted 4-Spiro[cycloalkane(tetrahydropyran)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolines]. Russ J Org Chem 59, 1884–1891 (2023). https://doi.org/10.1134/S1070428023110064
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DOI: https://doi.org/10.1134/S1070428023110064