Studies on the syntheses of heterocyclic compounds. Part CDXXI. General synthesis of 7,8-dioxygenated 1-benzyl-1,2,3,4-tetrahydroisoquinolines and elucidation of the structure of caseadine
{"title":"Studies on the syntheses of heterocyclic compounds. Part CDXXI. General synthesis of 7,8-dioxygenated 1-benzyl-1,2,3,4-tetrahydroisoquinolines and elucidation of the structure of caseadine","authors":"T. Kametani, T. Nakano, K. Shishido, K. Fukumoto*","doi":"10.1039/J39710003350","DOIUrl":null,"url":null,"abstract":"Bischler–Napieralski reactions of the phenolic bromo-amides (11c and d)[prepared by condensation of 5-benzyloxy-2-bromo-4-methoxyphenethylamine (9) with 3,4-dimethoxy-(10a) and 3,4-methylenedioxy-phenacetyl chloride (10b) followed by debenzylation] and reduction of the resultant benzyldihydroisoquinolines (12a and b) gave the 1-benzyl-5-bromo-1,2,3,4-tetrahydro-8-hydroxy-7-methoxyisoquinolines (13a and b). The former (13a) was converted into 1-hydroxy-2,10,11-trimethoxyberbine (3), which was different from caseadine.","PeriodicalId":17245,"journal":{"name":"Journal of The Chemical Society C: Organic","volume":"40 1","pages":"3350-3354"},"PeriodicalIF":0.0000,"publicationDate":"1971-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"5","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of The Chemical Society C: Organic","FirstCategoryId":"1085","ListUrlMain":"https://doi.org/10.1039/J39710003350","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
引用次数: 5
Abstract
Bischler–Napieralski reactions of the phenolic bromo-amides (11c and d)[prepared by condensation of 5-benzyloxy-2-bromo-4-methoxyphenethylamine (9) with 3,4-dimethoxy-(10a) and 3,4-methylenedioxy-phenacetyl chloride (10b) followed by debenzylation] and reduction of the resultant benzyldihydroisoquinolines (12a and b) gave the 1-benzyl-5-bromo-1,2,3,4-tetrahydro-8-hydroxy-7-methoxyisoquinolines (13a and b). The former (13a) was converted into 1-hydroxy-2,10,11-trimethoxyberbine (3), which was different from caseadine.