Some reactions of 3-cyano-4-(p-methoxyphenyl)-5-oxo-5,6,7,8-tetrahydro-quinoline-2(1H)-thione; Synthesis of new tetrahydroquinolines and tetrahydrothieno[2,3-b]quinolines | ||||
| Assiut University Journal of Multidisciplinary Scientific Research | ||||
| Volume 45, Issue 1, June 2016, Page 24-32 PDF (303.88 K) | ||||
| Document Type: Novel Research Articles | ||||
| DOI: 10.21608/aunj.2016.221638 | ||||
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| Abstract | ||||
| In this paper, 3-cyano-4-(p-methoxyphenyl)-5-oxo-5,6,7,8-tetrahydroquinoline-2(1H)-thione (2) was prepared and reacted with methyl iodide to give the corresponding 2-methylthio derivative 3. Fusion of compound 2 or 3 with hydrazine hydrate produced the aminopyrazolotetrahydroquinoline-5-hydrazone 4. Reaction of both compounds 2 and 3 with phenylhydrazine or thiosemicarbazide led to the formation of condensation products 6a,b and 9a,b respectively. Reaction of cyanoquinolinethione 2 with some α-halocarbonyl compounds namely; ethyl chloroacetate, chloroacetamide, chloro-N-(p-tolyl)acetamide and phenacyl bromide gave the corresponding alkylated products 10a-d. On treatment of the latter compounds with sodium ethoxide in boiling ethanol, they underwent intramolecular Thorpe-Zeigler cyclization affording the corresponding tetrahydrothieno[2,3-b] quinolines 11a-d. The elemental analyses and spectroscopic data of all compounds are in agreement with their proposed structures. | ||||
| Keywords | ||||
| hydrazono compounds; thiosemicarbazones; tetrahydroquinolines; tetrahydrothienoquinolines | ||||
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