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The Synthesis of Spiro[tetrahydroisoquinoline‐piperidines] and related compounds
Author(s) -
Berney Daniel,
Jauner Theodor
Publication year - 1975
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19750580109
Subject(s) - chemistry , tetrahydroisoquinoline , stereochemistry , schmidt reaction , medicinal chemistry
The reaction of 3,4‐dimethoxyphenethylamine with some cyclic aminoketones in the presence of polyphosphoric acid afforded 1‐spiro‐tetrahydroisoquinolines. A two‐step procedure starting from veratrylamine and amino‐ketones gave 3‐spiro‐tetrahydroisoquinolin‐4‐ones. The Schmidt rearrangement of 5,6‐dimethoxy‐3‐spiro‐indan‐1‐ones yielded 4‐spiro‐tetrahydroisoquinolin‐1‐ones.