Diazabenzobicyclo[3.3.1]nonane系化合物の研究(第3報) : (8-Methoxy-1,2,3,4,5,6-hexahydro-1,5-imino-3-benzazocine誘導体の合成とN→N' Acyl転位の一新例について
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Methyl 1-phthalimidomethyl-6-methoxy-3,4-dihydroisoquinoline-3-carboxylate (IV) was obtained by a Bischler-Napieralski reactioh of methyl m-methoxy α-(phthalimidoacet-amido)hydrocinnamate (III), which was prapared by the condensation of 3-(m-methoxy-phenyl)-alanine. (I) with phthalimidoacetyl chloride followed by esterification. IV was catalytically hydrogenated to afford a 1,2,3,4-tetrahydroisoquinoline derivative (V). Treatment of V with hydrazine hydrate and then with hydrochloric acid gave 8-methoxy-1,2,5,6-tetrahydro-1,5-imino-3-benzazocin-4(3H)-one(VI). Reduction of VI with lithium aluminum hydride afforded 8-methoxy-1,2,3,4,5,6-hexahydro-1,5-imino-3-benzazocine (VII). 3,11-Dimethyl-8-methoxy-1,2,3,4,5,6-hexahydro-1,5-imino-3-benzazocine (VIII) was obtained by methylation of VII with methyl iodide in the presence of potassium carbonate. Finally, VII was acetylated with acetic anhydride and the product was reduced with lithium aluminum hydride to 3,11-diethyl derivative (XI). A new example of N→N' acyl migration is presented. When 8-methoxy-11-acetyl-1,2,5,6-tetrahydro-1,5-imino-3-benzazocin-4(3H)-one (XII) was reduced with lithium aluminum hydride followed by acetylation, a normal product (XIV) and an N→N' acetyl-migrated product (XIV') were obtained.
- 公益社団法人日本薬学会の論文
- 1966-03-25
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