Synthesis of 3-aminomethyl-2-aryl- 8-bromo-6-chlorochromones.
[reaction: see text] An efficient synthetic route to Cbz-protected 3-aminomethyl-2-aryl-8-bromo-6-chlorochromones has been developed. 3-Aryl-1-(3-bromo-5-chloro-2-hydroxyphenyl)-2-propen-1-one or 2-aryl-8-bromo-6-chlorochroman-4-one could be reacted under Mannich conditions yielding 2-aryl-8-bromo-6-chloro-3-methylenechroman-4-one, which was further converted to the target compound via an aza-Michael reaction followed by an SeO(2) oxidation. This procedure represents a new method to introduce a primary aminomethyl group at the 3-position of a 2-arylchromone scaffold. The Cbz-protected 3-aminomethyl-2-aryl-8-bromo-6-chlorochromones can, e.g., be used in the synthesis of chromone-based beta-turn peptidomimetics.
Wallén
Erik A A
EA
Department of Chemistry, Medicinal Chemistry, Göteborg University, SE-412 96 Göteborg, Sweden.
Dahlén
Kristian
K
Grøtli
Morten
M
Luthman
Kristina
K
D000588:Amines / Q000737:chemistry; D040761:Biomimetic Materials / Q000737:chemistry; D002867:Chromones / Q000737:chemistry*; D005419:Flavonoids / Q000138:chemical synthesis*; D008956:Models, Chemical; D010084:Oxidation-Reduction; D010455:Peptides / Q000737:chemistry; D018036:Selenium Compounds / Q000737:chemistry; D064588:Selenium Oxides; D013237:Stereoisomerism
D000588:Amines; D002867:Chromones; D005419:Flavonoids; D010455:Peptides; D018036:Selenium Compounds; D064588:Selenium Oxides