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Synthesis of Thiazolidines, Oxadiazoles, Thiadiazoles and Triazoles derived from 6-nitro-2-quinolone | ||
| Al-Mustansiriyah Journal of Science | ||
| Article 1, Volume 21, Issue 5, 2010, Pages 244-250 | ||
| Author | ||
| Abdul-Hussain K. Sharba | ||
| Abstract | ||
| In this work, 6-nitro coumarin [1] has been prepared by nitration of coumarin and then converted into 6-nitro-1-aminoquinoline-2-one [2b]. The azomethines [3a-e] were prepared from the corresponding aryl aldehydes and ketones with [2b]. Treatment of compounds [3a-e] with mercapto acetic acid gave the thiazolidinone derivatives [4-5]. Moreover the reaction of compound [1] with glycine afforded the acetic acid derivative of 2-quinolone [6], which was converted into the acid hydrazide [7]. Treatment of compound [7] with carbon disulfide in potassium hydroxide gave the oxadiazole derivative [8]. The reaction of compound [6] with thiosemicarbazide yielded 2-[(6-nitro-2-oxoquinolin-1(2H)-yl)acetyl] hydrazine carbothioamide [9]. Reaction of compound [9] with NaOH leads to ring closure giving 1-[(5-mercapto-4H-1,2,4-triazol-3-yl)methyl]-6-nitro quinolin-2-(1H)-one [10a-b]. In addition, treatment of compound [9] with H2SO4 leads to ring closure also giving the thiadiazole derivative of 6-nitro-2-quinolone [11]. | ||
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