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.
Zhang
J
J
Department of Chemistry, Advanced SynTech, 9800 Bluegrass Parkway, Louisville, KY 40299, USA.
Goodloe
W P
WP
Lou
B
B
Saneii
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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