Isoquinoline, 1 -bromo-5,6,7,8-tetrahydro

The mechanism of palladium-catalyzed intramolecular cyclization of o-bromo(aminoalkyl)benzenes has been discussed earlier (see Scheme 50 in Section IV,A,4). An example illustrating the use of this approach for the synthesis of 2,3,4,5-tetrahydro-l//-2-benzazepin-l-ones is given in Scheme 17386 and examples indicating the synthesis of isoquinoline derivatives are given earlier (see Scheme 146 in Section V,A,4). 

A solution of N-(2-aminobenzyl)-l-phenyl-2-methylaminoethanol-l was prepared by the reaction of a-bromo-acetophenone and (2-nitrobenzyl)methylamine, followed by hydrogenation of the nitro group by means of nickel on diatomaceous earth at room temperature and reduction of the CO group by means of sodium borohydride. The intermediate thus produced was dissolved in 100 ml of methylene chloride and introduced dropwise into 125 ml of sulfuric acid at 10° to 15°C. After a short standing, the reaction mixture was poured onto ice and rendered alkaline by means of a sodium hydroxide solution. By extraction with ether, there was obtained l,2,3,4-tetrahydro-2-methyl-4-phenyl-8-amino-isoquinoline. The base is reacted with maleic acid to give the maleate melting point of the maleate 199° to 201°C (from ethanol). 

C25Hllt04 152906-16-6) sec Orlistat 6 -(acetyloxy)-5-bromo-2, 3 ,8, 8 a-tetrahydro-5,-meth-oxy-r-methylspiro[2-cyclohexene-l,7 (r//)-cyclopent[i/l-isoquinolin]-4-onc... 

Recently, the antieancer mechanism of noscapine derivative Red-Br-nos, (/ )-9-bromo-5-((iS)-4,5 -dimethoxy-1,3 -dihydroisobenzofuran-1 -yl)-4-methoxy-6-methyl-5,6,7,8-tetrahydro-[l,3]-dioxolo[4,5-g]isoquinoline, has been described in human prostate eaneer PC-3 eells... 

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