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Synthesis and Some Transformations of Ethyl 6,7-Dimethoxy-2',3',5',6'-tetrahydro-3H-spiro[isoquinoline-4,4'-pyran]-1-carboxylate

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Abstract

The reaction of {[4-(3,4-dimethoxyphenyl)tetrahydro-2H-pyran-4-yl]methyl}amine with diethyl oxalate was used to synthesize ethyl 2-({[4-(3,4-dimethoxyphenyl)tetrahydro-2H-pyran-4-yl]methyl}amino)-2-oxoacetate, whose cyclization with phosphorus oxychloroxide under Bischler–Napieralski reaction conditions gave 1-carbethoxy-substituted dihydroisoquinoline. By treatment with methylamine the latter was converted to the corresponding N-methylcarboxamide derivative, which was reduced to obtain N-methyl-6,7-dimethoxy-2,2',3,3',5',6'-hexahydro-1H-spiro[isquinoline-4,4'-pyran]-1-carboxamide. A series of novel derivatives of 4-spirotetrahydropyran-substituted dihydro- and tetrahydroisoquinolines with various different substituents in the first and second positions of the heterocyclic ring were prepared.

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Authors and Affiliations

  1. Scientific Technological Center of Organic and Pharmaceutical Chemistry, National Academy of Sciences of Armenia, 0014, Yerevan, Armenia

    A. A. Aghekyan & H. A. Panosyan

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  1. A. A. Aghekyan
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  2. H. A. Panosyan
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Correspondence to A. A. Aghekyan.

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Translated from Zhurnal Organicheskoi Khimii, 2022, Vol. 58, No. 11, pp. 1159–1167 https://doi.org/10.31857/S0514749222110040.

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Aghekyan, A.A., Panosyan, H.A. Synthesis and Some Transformations of Ethyl 6,7-Dimethoxy-2',3',5',6'-tetrahydro-3H-spiro[isoquinoline-4,4'-pyran]-1-carboxylate. Russ J Org Chem 58, 1581–1588 (2022). https://doi.org/10.1134/S1070428022110045

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