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Isoquinolines, Part 1 (The Chemistry of Heterocyclic by Guenter Grethe

By Guenter Grethe

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999 1V. Reactions 31 protonated form proved to be linearly correlated with those of the free base and do not display a different reactivity pattern, thus suggesting that different mechanisms of substitution must be involved to result in the observed orientations. Under conditions of lower acidity. 2dihydroisoquinoline system 101 (Scheme 5). The r-electron densities for this intermediate have been calculated. and a strong preference for electrophilic attack at C-4 is predicted. jcbemc 5 A more quantitative comparison o f the susceptibilities of sites to electrophilic substitution was obtained by the technique of acid-catalyzed deuterium e ~ c h a n g e .

12). When 159 is similarly reducedZMa mixture of 160 and 161 is produced (Eq. 13). Birch reduction of ,-methyl6-methoxy-1,2,3,4-tetrahydroisoquinoline (162) yields the expected hexahydro compound 163,2h7and similar treatment"' of 164 gave 165. In a Properties and Reactions of Isoquinolines SO I &Me OMe 155 156 later studyZh" 2-methyl- 1,2,3,4-tetrahydroisoquinoline was reduced to 166 by using lithium in liquid ammonia in the presence of ethanol. An interestMe0 Me0 NU-MeOti-NH, m N 162 164 M e W N M e 163 165.

A further sequence of addition reactions2w was studied in which the intermediate 1,2-dihydroisoquinoIine was dehydrogenated to the aromatic structure with chloranil (Eq. 10). B. Reduction and Oxidation (a) Introduction The various oxidation states of the heteroring in isoquinoline derivatives are summarized in Schemes 11 and 12, together with an indication of the possible modes of interconversion using oxidation or reduction reactions. 45 IV. t 48 I Me-CHOCOMe 9 --CH2NMeCH0 15 h k N 3 12 0 Scheme 11 (b) Reducrion (i) CATALYTIC.

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