Synthesis and Conformation of (5 R ,8 R ,10 R )‐8‐(Methylthiomethyl)ergoline‐6‐carboxamidine | Zendy

Nordmann René | Zendy; Loosli HansRudolf | Zendy

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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

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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