1400899-99-1Relevant academic research and scientific papers
Synthesis of oxadiazoles encompassing naphtho [2,1-b] thiophene as novel antimicrobial agents
Kusuma,Vaidya,Nagashree,Mahadevan
, p. 309 - 314 (2013/09/24)
The required starting material ethyl naphtho [2,1-b] furan-2-carboxylate 2 has been synthesized by the reaction between ethyl chloroacetate and 2-hydroxy-1-naphthaldehyde 1, which in turn was obtained by employing Reimer-Tiemann reaction using 2-naphthol. The ester 2 on thionation with phosphorus pentasulphide produced two compounds viz., ethyl naphtho [2,1-b] thiophene-2-carboxylate 3 and ethyl naphtho [2,1-6] furan-2-carbothioate 4. The compounds 3 and 4 were separated by column chromatography and the compound 3 was converted into naphtho [2,1-b] thiophene-2-carbohydrazide 5 by reacting with hydrazine hydrate. The reaction of carbohydrazide 5 with various aromatic aldehydes resulted in the formation of corresponding Schiff bases 6a-e. The synthesis of 5-(naphtho [2,1-b] thiophen-2-yl)-3-(prop-1-en-2-yl)-2,3-dihydro-1, 3,4-oxadiazoles 7a-e was achieved by adopting a simple one pot procedure which involved reaction of Schiff bases 6a-e with acetic anhydride. All the synthesized compounds have been characterized by IR, 1H NMR spectroscopy and mass spectrometry. All the newly synthesized compounds showed moderate to mild antimicrobial activity when evaluated by cup-plate method. These findings indicated that the title compounds have the property to kill the microbes to some extent when compared with standard drug.
