Synthesis of 3-dialkylaminochromans via thallium(III)-induced cyclization of allyl aryl ethers.
The sulfur-containing 3-alkylaminochromans, 5-methoxy-3-[N-(2- methylthioethyl)-propylamino]chroman (15), 5-hydroxy-3-[N-(2-methylthioethyl)propylamino]chroman (5) and 5-methoxy-8-methylthio-3-(dipropylamino)chroman (6), have been prepared from 8-bromo-5-methoxy-3-chromanol (11). This precursor was synthesized from 3-allyloxy-4-bromoanisole (8), by a thallium(III)-mediated ring-closure reaction. Compound 11 also served as starting material for the synthesis of 8-bromo-3-(dipropylamino)-5-methoxychroman (7).
Andersson
B
B
Department of Pharmacology, University of Göteborg, Sweden.
Wikström
H
H
Hallberg
A
A
D002839:Chromans / Q000138:chemical synthesis* / Q000494:pharmacology; D003500:Cyclization; D015259:Dopamine Agents; D015394:Molecular Structure; D011985:Receptors, Serotonin / Q000187:drug effects; D013329:Structure-Activity Relationship; D013793:Thallium
D002839:Chromans; D015259:Dopamine Agents; D011985:Receptors, Serotonin; D013793:Thallium