30454-83-2Relevant academic research and scientific papers
Microwave-assisted solid-phase synthesis of 4,5-dihydroxy-1,3-dialkyl-4,5- diarylimidazolidine-2-thione and thiohydantoins
Ghanbari, Mohammad M.,Mahdavinia, Gholam H.,Safari, Javad,Naeimi, Hossein,Zare, Mehdi
experimental part, p. 2414 - 2420 (2011/08/05)
4,5-Dihydroxy-1,3-dialkyl-4,5-diarylimidazolidine-2-thione are obtained in good yields from the 1:1 addition reaction between benzil derivatives and thiourea derivatives in the solid phase. These compounds undergo smooth rearrangement followed by a hydrogen shift to produce thiohydantoins in excellent yields.
Mechanistic Studies in the Chemistry of Thiourea. Part 1. Reaction with Benzil Under Alkaline Conditions
Broan, Christopher J.,Butler, Anthony R.,Reed, David,Sadler, Ian H.
, p. 731 - 740 (2007/10/02)
Benzil reacts under alkaline conditions with 1,3-dimethylthiourea to form 4,5-dihydroxy-1,3-dimethyl-4,5-diphenyltetrahydroimidazole-2-thione (1); with 1-methylthiourea to form 3-methyl-5,5-diphenyl-2-thiohydantoin (9); and with thiourea to form both the corresponding hydantoin and 3a,7a-diphenyltetrahydroimidazoimidazole-2,5-dithione (19).The use of high field n. m. r. spectroscopy and benzil labelled with carbon-13 in the carbonyl group has permitted delineation of the reaction mechanisms and detection of a number of transient intermediates.
