Tetralin, 8-hydroxy-2- synthesis

Whilst studying the metabolism of dopaminergic and serotonergic agonists, WikstrSm etdl required the S- and 8-hydroxy-2-(di-n-propylamino)tetralins. The synthesis of the S-isomer (11) is shown in Scheme 4. The yield with nitrobenzene was poor, but this was the best reagent for the required conversion. 

Table 5.1. Synthesis of tetralines by intermolecular trapping of hydroxy-o-quinodimethanes.

SYNTHESIS To a solution of 49.2 g 5,6,7,8-tetrahydronaphthol (5-hydroxy-tetralin) in 100 mL MeOH, there was added 56 g methyl iodide followed by a... 

Naphthalene 1,2-oxide. Yagi and Jerina have reported a new method for synthesis of arene oxides. The starting material for the preparation of naphthalene 1,2-oxide (5) is I-hydroxy-2-bromotetralin, (I), which is acetylated with irifluoroacctic anhydride in chloroform to give (2) in 84 % yield. This is converted into the dibromide (3) by treatment with NBS (note that tetralin 1,2-epoxidc is uiLstable to bromination with NBS). The... 

Glase, S.A. (1995) Synthesis and dopaminergic activity of pyridine analogs of 5-hydroxy-2-(di-//-propylamino)tetralin. J. Med. Chem. 38, 3132-3137. 

Zhuang, Z. (1993) Synthesis of (R,S)-trans-8-hydroxy-2-[N- -propyl-N-(3 -iodo-2 -propenyl)amino]tetralin (trans-8-OH-PIPAT) a new 5-HT1A receptor ligand. J. Med. Chem. 36,3161-3165. 

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