Solid-phase synthesis of tetrahydro-1,4-benzodiazepin-2-one derivatives.
An efficient method for solid-phase construction of tetrahydro-1,4-benzodiazepin-2-one scaffold is described. Polymer-bound 4-(bromomethyl)-3-nitrobenzoic acid was reacted with alpha-amino acid methyl esters, followed by nitro group reduction and hydrolysis. Subsequent intramolecular cyclization and alkylation at N(4) afforded the structurally diverse products in high yields and excellent purities.
Department of Chemistry, Advanced SynTech, 9800 Bluegrass Parkway, Louisville, KY 40299, USA.
J
J
Zhang
W P
WP
Goodloe
B
B
Lou
H
H
Saneii
D000478:Alkylation; D001569:Benzodiazepines / Q000737:chemistry*; D001570:Benzodiazepinones / Q000138:chemical synthesis* / Q000737:chemistry*; D020650:Combinatorial Chemistry Techniques; D003500:Cyclization; D008401:Gas Chromatography-Mass Spectrometry; D006868:Hydrolysis; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D010084:Oxidation-Reduction; D011108:Polymers / Q000737:chemistry*; D014466:Ultraviolet Rays
D001570:Benzodiazepinones; D011108:Polymers; D001569:Benzodiazepines; C022854:tetrahydro-1,4-benzodiazepin-2-one