Assisted hydrolysis of cis-2-(3-phenylthioureido) cyclo pentane-carbonitrile in alkaline solution. Solvent dependent switch from hydrolysis to rearrangement of the …

…, IB Blagoeva, FL Chubb, JT Edward…

Index: Atay, Ergun; Blagoeva, Iva B.; Chubb, Francis L.; Edward, John T.; Pojarlieff, Ivan G.; Toteva, Maria M. Canadian Journal of Chemistry, 2000 , vol. 78, # 1 p. 84 - 94

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Citation Number: 5

Abstract

The cis and trans isomers of 2-(3-phenylthioureido) cyclopentanecarbonitrile, 1, and the respective carboxamides, 3, and acids, 4, have been prepared. Acid cyclization of both nitriles, faster with the cis isomer, gave the more stable cis-2-thiooxo-cyclopenta [d] pyrimidin- 4-one, 7. In base cis-1 formed the cis 4-imino-2-thiooxopyrimidine 2 which in aqueous alkali broke down via 3 to the acid 4; while in the presence of 66% acetonitrile 2 rearranged to ...