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Benz[ cd ]indoles. Part III. A New Stereospecific Synthesis of Dihydrolysergic Acid and an Entry to 14‐Substituted Derivatives
Author(s) -
Haefliger Walter E.
Publication year - 1984
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.19840670732
Subject(s) - chemistry , stereospecificity , ring (chemistry) , indole test , closure (psychology) , tricyclic , combinatorial chemistry , stereochemistry , organic chemistry , catalysis , economics , market economy
A new convenient synthesis of dihydrolysergic acid is described, which allows the preparation of substituted derivatives, especially those with different substitutents in the aromatic ring. Starting from appropriately substituted 5‐nitro‐2‐tetralones, the synthesis leads via a tricyclic isonitrile to the indole‐ring closure as the last step, thus circumventing the troublesome protection/deprotection of the latter.