33238-58-3Relevant academic research and scientific papers
REACTIONS OF ETHYL 2-ALKYL-3-OXOBUTANOATE WITH THIOUREA AND METHYLTHIOUREA
Kavalek, Jaromir,Machacek, Vladimir,Sterba, Vojeslav
, p. 1872 - 1877 (2007/10/02)
The reaction of ethyl-3-oxobutanoate with N-methylthiourea in alkoxide medium gives a mixture (1:20) of 1,6-dimethyl-2-thiouracil and 3,6-dimethyl-2-thiouracil: the latter isomer has been isolated from the mixture and the former isomer has been prepared by independent synthesis.Dissociation constants of ethyl 2-alkyl-3-oxobutanoates (alkyl = methyl, butyl or isopropyl) have been measured in methanol.Reaction of these esters with thiourea and N-methylthiourea gives the corresponding alkyl derivatives of 6-methyl-2-thiouracil.Kinetics of these reactions have been measured in methoxide medium.Effects of the alkyl groups on the reaction rates have been investigated, and a reaction mechanism is suggested.
STUDY OF REACTION OF THIOUREA WITH ETHYL 3-OXOBUTANOATE
Kavalek, Jaromir,El-Bahaie, Said,Machacek, Vladimir,Sterba, Vojeslav
, p. 732 - 739 (2007/10/02)
Base-catalyzed formation of 6-methyl-2-thiouracil (III) by reaction of thiourea (I) with ethyl 3-oxobutanoate (II) involves N-(3-oxobutanoyl)thiourea (XI) as the reaction intermediate.In acid medium the compounds I and II do not react.In contrast to literature data, base-catalyzed cyclization of ethyl 3-thioureido-2-butenoate (IV) does not produce the compound III, but produces 2-amino-4-methyl-6-oxo-1,3-thiazine.
