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.

中文翻译：

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新型苯并二氧杂环戊烯取代的4-螺[环烷(四氢吡喃)-6,7-二甲氧基-1,2,3,4-四氢异喹啉]的合成及其抗心律失常活性

摘要

1-(3,4-二甲氧基)苯基环烷甲烷-和4-(3,4-二甲氧基苯基)四氢吡喃-4-甲胺与苯并[ d ][1,3]间二氧杂环己烷-5-碳酰氯反应合成N -取代的苯并[ d ][1,3]间二氧杂环己烷-5-甲酰胺。后者与三氯氧磷环化得到二氢异喹啉，随后用硼氢化钠还原为螺取代的四氢异喹啉，随后进行埃施韦勒-克拉克反应得到N-甲基衍生物。起始胺与苯并[ d ][1,3]间二氧杂环己烷-5-甲醛缩合形成希夫碱，用硼氢化钠还原得到相应的仲胺——四氢异喹啉的无环类似物。后者产物在 Eschweiler-Clark 反应下环化，合成了N-苯并二氧杂环戊烯甲基取代的四氢异喹啉。