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Synthesis and Conformation of (5R,8R,10R)-8-(Methylthiomethyl)ergoline-6-carboxamidine

✍ Scribed by René Nordmann; Hans-Rudolf Loosli

Publisher: John Wiley and Sons
Year: 1985
Tongue: German
Weight: 376 KB
Volume: 68
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.19850680428

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✦ Synopsis

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).

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