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Abstract
In this paper the synthesis of 4-substituted benzoxazole [3,4-b] imidazole (9,10) and 4-aryl hexahydrobenzoxazole [3,4-b] imidazole (13,14) is reported. Glycine was treated with benzoyl chloride or p-nitrobenzoyl chloride to give N-aroyl glycine (1,2), the reaction of N-aroyl glycine with thionyl chloride followed by treatment the product (3,4) with ammonium hydroxide to give N-aroyl glycine amide (5,6). Treatment of the amide with 1-bromocyclohexanone gave N-methylene-2-hexahydrobenzoxazole) aryl amide (7,8), cyclization of this gave product (9,10), whereas the compounds (13,14) was synthesized from o-aminophenol and the acid chlorides to give N-methylene (2-benzoxazole) aryl amide (11,12) which cyclized with phosphorous oxychloride to give the products (13,14). The structure of all synthesized compounds were confirmed by physical and spectral data.
Highlights
The preparation of 2-methyl benzoxazole by Ladenbyrg (1876) marks the first recognition of oxazole(1), but the name of these compounds comes from Hantzsch (1887) when gave that name to this class of compounds(2)
Preparation of N-aroyl glycine (1,2)(10) (0.02 mol, 1.5 g) of glycine in 20 ml of 1 N sodium hydroxide was cooled at 0-5 °C and the cold solution was added dropwise to a solution of (0.02 mol) of acid chloride in (30 ml) of chloroform
The reaction mixture was cooled and the formed solid was collected by filtration
Summary
The preparation of 2-methyl benzoxazole by Ladenbyrg (1876) marks the first recognition of oxazole(1), but the name of these compounds comes from Hantzsch (1887) when gave that name to this class of compounds(2). Benzoxazole may be prepared by the reaction between oaminophenols and carboxylic acid(4) as a simple method. Preparation of N-aroyl glycine (1,2)(10) (0.02 mol, 1.5 g) of glycine in 20 ml of 1 N sodium hydroxide was cooled at 0-5 °C and the cold solution was added dropwise to a solution of (0.02 mol) of acid chloride in (30 ml) of chloroform.
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