Electrochemical Oxidation of Ergolines

✍ Scribed by Karlheinz Seifert; Nguyen Minh Phuong; Beverly R. Vincent

• Publisher: John Wiley and Sons
• Year: 1992
• Tongue: German
• Weight: 321 KB
• Volume: 75
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.19920750125

✦ Synopsis

An electrochemical procedure for the preparation of ~-3-alkoxy-halogen-2,3-dihydro-6-methyl-2-oxoergolines-I is described.

Introduction.

~ Ergot is a drug known to mankind for centuries, and some ergot derivatives such as ergotamine, 9,10-dihydroergotamine, and 2-bromo-a -ergocryptine are presently used as therapeutic agents. The search continues for more active and especially more specifically acting ergot compounds [ 11. For this reason, the oxidative electrochemical functionalization of the ergoline skeleton attracts interest [2] [3]. Results. ~ In the cyclic voltammetry of 9,lO-dihydrolysergic acid methyl ester (1; Scheme l ) , two irreversible peaks of oxidation at 1.01 V and 1.35 V are observed R* R2 1 C02CH3 2 CH20H Scheme I R2 graphite electrodes/HX/R1 OHIH20 € = 1.60V 3a