Studies on the Syntheses of Heterocyclic Compounds. CDLXXXIII. Synthesis of Homoaporphine and Attempts to Synthesize C-Noraporphine by Pschorr Reaction

TETSUJI KAMETANI; TAKUO NAKANO; CHIZUKO SEINO; SHIROSHI SHIBUYA; KEIICHIRO FUKUMOTO; T.R. GOVINDACHARI; K. NAGARAJAN; B.R. PAI; P.S. SUBRAMANIANI

doi:10.1248/cpb.20.1507

Studies on the Syntheses of Heterocyclic Compounds. CDLXXXIII. Synthesis of Homoaporphine and Attempts to Synthesize C-Noraporphine by Pschorr Reaction

TETSUJI KAMETANI, TAKUO NAKANO, CHIZUKO SEINO, SHIROSHI SHIBUYA, KEIICHIRO FUKUMOTO, T.R. GOVINDACHARI, K. NAGARAJAN, B.R. PAI, P.S. SUBRAMANIANI

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JOURNAL FREE ACCESS

1972 Volume 20 Issue 7 Pages 1507-1512

DOI https://doi.org/10.1248/cpb.20.1507

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Abstract

Photolysis of the diazonium salt derived from 1-(2-amino-4-hydroxy-5-methoxy-phenethyl)-7-hydroxy-1, 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 1-(2-aminophenyl)-1, 2, 3, 4-tetrahydro-6, 7-dimethoxy-2-methylisoquinoline (XXI) gave an abnormal product, 3, 4-dihydro-6, 7-dimethoxy-1-phenylisoquinoline (XXV), in addition to the deamination product (XXII) and the phenolic isoquinoline (XXIII).

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