6533b851fe1ef96bd12a96fb

RESEARCH PRODUCT

Partialsynthese neuer Ergolinderivate aus Clavinalkaloiden, 4. Mitt. N-1-, C-2- und N-6-monosubstituierte Agroclavine

E. EichChristoph BeckerReinhold Sieben

subject

Indole testchemistry.chemical_classificationPotassium amideStereochemistryIodidePharmaceutical ScienceAlkylationErgolinechemistry.chemical_compoundchemistryDrug DiscoverymedicineAgroclavineCyanogen bromideAlkylmedicine.drug

description

Agroclavin (1) wird in flussigem Ammoniak/Kaliumamid mit Alkyliodid am Indolstickstoff alkyliert. 1 last sich mit N-Iodsuccinimid zu 2-Iod-1 (3) umsetzen. Mit der Bromcyan-Methode wird 6-Nor-1 (4b) gewonnen und danach an N-6 alkyliert. Partial Synthesis of New Ergoline Derivatives from Clavine Alkaloids, IV: Agroclavines Monosubstituted at N-1, C-2, and N-6 Agroclavine (1) is alkylated at the indole nitrogen with alkyl iodide in ammonia/potassium amide. It is convertible to 2-iodo-1 (3) with N-iodosuccinimide. Compound 6-nor-1 can be prepared by means of the cyanogen bromide method; alkylation at N-6 is described exemplarily for the ethyl derivative.

https://doi.org/10.1002/ardp.19853180306