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Synthesis and Conformation of (5 R ,8 R ,10 R )‐8‐(Methylthiomethyl)ergoline‐6‐carboxamidine
Author(s) -
Nordmann René,
Loosli HansRudolf
Publication year - 1985
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.19850680428
Subject(s) - chemistry , thiourea , cyanamide , stereochemistry , ring (chemistry) , guanidine , organic chemistry
Abstract The title compound 7 and two related novel ergolines have been synthesised from (5 R ,8 R ,10 R )‐8‐(methyl‐thiomethyl)ergoline‐6‐carbonitrile ( 4 ). The guanidine function of 7 induces a boat conformation of ergoline‐ring D, as demonstrated by a careful NMR spectroscopic analysis of 7 and its N ‐hydroxy congener 6 . Diphenylphosphinodithioic acid has been used to convert the cyanamide function of 4 into the thiourea function at (5 R ,8 R ,10 R )‐8‐(methylthiomethyl)ergoline‐6‐thiocarboxamide ( 5 ).