Bibliographic Details
| Title: |
Synthesis and Some Transformations of Ethyl 6,7-Dimethoxy-2',3',5',6'-tetrahydro-3H-spiro[isoquinoline-4,4'-pyran]-1-carboxylate. |
| Authors: |
Aghekyan, A. A.1 (AUTHOR) aaghekyan@mail.ru, Panosyan, H. A.1 (AUTHOR) |
| Source: |
Russian Journal of Organic Chemistry. Nov2022, Vol. 58 Issue 11, p1581-1588. 8p. |
| Subject Terms: |
*TETRAHYDROISOQUINOLINES, *OXALATES, *RING formation (Chemistry), *AMINES, *CARBOXAMIDES, *PHOSPHORUS |
| 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. [ABSTRACT FROM AUTHOR] |
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