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A Convenient and Facile Hantzsch Synthesis of Aryl Imidazo[1,2‐ b ]Isoxazolyl‐ N ‐aryl Thiazol Amines
Author(s) -
Rajanarendar E.,
Thirupathaiah K.,
Ramakrishna S.,
Nagaraju D.
Publication year - 2016
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.2518
Subject(s) - chemistry , aryl , chloroacetyl chloride , phenacyl , medicinal chemistry , phenacyl bromide , organic chemistry , chloride , alkyl
The Hantzsch synthesis of novel aryl imidazo[1,2‐ b ]isoxazolyl‐ N ‐aryl thiazol amines 5 analogues were described. Reaction of 3‐aminoisoxazole 1 with substituted phenacyl bromides 2 in dry ethanol afforded the corresponding 6‐methyl‐3‐arylimidazo[1,2‐ b ]isoxazoles 3 in good yields. Compounds 3 on reaction with chloroacetyl chloride in 1,4‐dioxane furnished the corresponding 2‐chloro‐1‐(6‐methyl‐3‐arylimidazo[1,2‐ b ]isoxazol‐2‐yl)ethanones 4 . Compounds 4 on heating with N ‐aryl thioureas in an oil bath underwent cyclization to afford the title compounds viz ., imidazo[1,2‐ b ]isoxazolyl‐ N ‐aryl thiazol amines 5 in moderate to good yields by Hantzsch synthesis.