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Reactivity of Hydroxy and Amino Derivatives of 2‐Phenyl‐1 H ‐imidazoline and 2‐Phenyl‐1 H ‐imidazole toward Isocyanates: Synthesis of Appropriate Carbamates and Ureas
Author(s) -
Pařík Patrik,
Jansa Josef,
Holešová Sylva,
Marek Aleš,
Klimešová Věra
Publication year - 2013
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.984
Subject(s) - chemistry , imidazole , reactivity (psychology) , isocyanate , imidazoline receptor , medicinal chemistry , diethylamine , ring (chemistry) , amidine , organic chemistry , polyurethane , medicine , alternative medicine , pathology
Reactivity of 2‐(4‐hydroxyphenyl)‐1 H ‐imidazoline and 2‐(4‐hydroxyphenyl)‐1 H ‐imidazole toward substituted phenyl isocyanates was studied. When mentioned imidazoline was treated with 2.5 equiv of substituted phenyl isocyanate, three N , O ‐dicarboxamides were prepared (substituents are H, 4‐NO 2 , and 4‐CH 3 ). Subsequently, N , O ‐diacetylated 2‐(4‐hydroxyphenyl)‐1 H ‐imidazoline was prepared and selective deprotection method was developed for preparation of 1‐acetyl‐2‐(4‐hydroxyphenyl)‐1 H ‐imidazoline using diethylamine in acetone. Six carbamates derived from this imidazoline were then prepared using 1.1 equiv of substituted phenyl isocyanates (substituents are H, 4‐CH 3 , 4‐OCH 3 , 4‐NO 2 , 4‐CN, and 3‐CF 3 ). Finally, two carbamates were prepared from 2‐(4‐hydroxyphenyl)‐1 H ‐imidazole (substituents are 4‐NO 2 and 4‐CN). No reactivity to imidazole ring was observed in this case. Eight derivatives were subjected to antimycobacterial screening. Concurrently, reactivity of 2‐(2‐aminophenyl)‐ and 2‐(2‐hydroxyphenyl)‐1 H ‐imidazole toward aliphatic and aromatic isocyanates was studied. Eight ureas were prepared using equivalent mixture of 2‐(2‐aminophenyl)‐1 H ‐imidazole and isocyanate (Et, Pr, isoPr, terc‐Bu, Cy, Ph, 4‐CH 3 C 6 H 4 , 4‐CNC 6 H 4 ). Similar attempts to obtain related carbamates from 2‐(2‐hydroxyphenyl)‐1 H ‐imidazole lead only to three substituted phenyl carbamates (substituents are 4‐CH 3 , 4‐NO 2 , and 4‐CN). In both cases, no reactivity to imidazole ring was observed again.