Studies on the synthesis of heterocyclic compounds CDLXXXIII. Synthesis of homoaporphines and attempts to synthesize C-noraporphines by Pschorr reaction

Kametani, Tetsuji ; Nakano, Takuo ; Seino, Chizuko ; Shibuya, Shiroshi ; Fukumoto, Keiichiro ; Govindachari, T. R. ; Nagarajan, K. ; Pai, B. R. ; Subramaniani, P. S. (1972) Studies on the synthesis of heterocyclic compounds CDLXXXIII. Synthesis of homoaporphines and attempts to synthesize C-noraporphines by Pschorr reaction Chemical & Pharmaceutical Bulletin (Tokyo), 20 . pp. 1507-1512. ISSN 0009-2363

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Abstract

Photolysis of the diazonium salt derived from l-(2-amino-4-hydroxy-5-methoxy-phenethyl)-7-hydrox}'-l;2,3,4-tetrahydro-6-methoxy-2-methylisoquinoline (V) gave, 1,11-dihydroxy-2,10-dimethoxyhomoaporphine (IX), which was identical with the rearranged product of kreysiginone (VII) by acid. The same reaction of l-(2-aminophenyl)-l,2,3,4-tetrahydro-6,7-dimethoxy-2-methylisoquinoline (XXI) gave an abnormal product, 3,4-dihydro-6,7-dimethoxy-l-phenylisoquino]ine (XXV), in addition to the deamination product (XXII) and the phenolic isoquinoline (XXIII).

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Deposited On:19 Jun 2012 07:21
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