Reactions of ethyl 2-alkyl-3-oxobutanoate with thiourea and methylthiourea
1983 ◽
Vol 48
(7)
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pp. 1872-1877
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Keyword(s):
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.
Keyword(s):
2014 ◽
Vol 20
(3)
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pp. 345-352
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Keyword(s):
1995 ◽
Vol 64
(10)
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pp. 953-966
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1978 ◽
Vol 4
(6)
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pp. 529-535
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1987 ◽
Vol 65
(10)
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pp. 2428-2433
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2018 ◽
Vol 43
(4)
◽
pp. 347-357
2005 ◽
Vol 70
(6)
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pp. 869-877
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