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Synthesis of 1‐halophenyl 4‐(2‐imidazolyl)‐1‐butanones and 5‐(2‐imidazolyl)‐1‐pentanones and their ketalization with glycerol
Author(s) -
Huang LiangFu,
Bauer Ludwig
Publication year - 1997
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570340405
Subject(s) - chemistry , amidine , hydrochloric acid , ketone , medicinal chemistry , ethanol , dimethoxyethane , dioxolane , organic chemistry , stereochemistry , electrode , electrolyte
An alternate synthesis of 1‐(2,4‐dichlorophenyl)‐4‐(2‐imidazolyl)‐1‐butanones 5d is presented after 1‐[(dimethylamino)methyl‐ and 1‐methyl]‐2‐lithioimidazole failed to be substituted satisfactorily by 2‐(2,4‐dichlorophenyl)‐2‐(3‐iodopropyl)‐1,3‐dioxolane ( 3b ). The Pinner addition of ethanol to 2‐(2,4‐dichlorophenyl)‐2‐(3‐cyanopropyl)‐1,3‐dioxolane yielded the corresponding imidate which was reacted with 1‐amino‐2,2‐dimethoxyethane to form an amidine. Hot dilute hydrochloric acid converted this ami‐dine to the 2‐imidazolyl ketone 5b . Syntheses of homologous 1‐(4‐chloro‐ and 2,4‐dichlorophenyl)‐4‐(2‐imidazolyl)‐1‐pentanones 20 are described. Ketalizations of 5 and 20 with glycerol formed imidazolyl 1,3‐dioxolanyl alcohols. Selective N ‐ and O ‐alkylations of some of these imidazolyl alcohols are described.