Paper
Studies on 3, 5-Dioxopiperidines and Related Compounds : Synthesis of 5-(3-tert-Butylamino-2-hydroxy) propoxy-1, 2, 3, 4-tetrahydro-2-oxo-1, 7-naphthyridine
Published Sep 25, 1981 · Y. Tamura, Ching Ling Chen, M. Fujita
Chemical & Pharmaceutical Bulletin
1
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Abstract
The 7-aza analog (1·HCl) of 5-(3-tert-butylamino-2-hydroxy) propoxy-3, 4-dihydrocarbostyril·hydrochloride (2·HCl, carteolol·HCl) was prepared as part of a search for new adrenergic receptor antagonists. Thermal treatment of 1-acetyl-3-benzylamino-5-oxo-3, 4-dehydropiperidine (3), derived from N-acetylpiperidine-3, 5-dione (4a) by treatment with acryloyl chloride, gave 7-acetyl-1-benzyl-2, 5-dioxo-1, 2, 3, 4, 5, 6, 7, 8-octahydro-1, 7-naphthyridine (7). Dehydrogenation of 7 on 5% palladium carbon, and subsequent reductive debenzylation with liquid ammonia and sodium gave 5-hydroxy-1, 2, 3, 4-tetrahydro-2-oxo-1, 7-naphthyridine (5). Alkylation of 5 with epichlorohydrin, treatment with alkali and amination with tert-butylamine gave 5-(3-tert-butylamino-2-hydroxy)-propoxy-1, 2, 3, 4-tetrahydro-2-oxo-1, 7-naphthyridine·hydrochloride (1·HCl) in 45% overall yield from 5.
5-(3-tert-butylamino-2-hydroxy) propoxy-1, 2, 3, 4-tetrahydro-2-oxo-1, 7-naphthyridinehydrochloride (1HCl) is a novel adrenergic receptor antagonist with potential therapeutic
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