1122-25-4Relevant articles and documents
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Spencer,T.A. et al.
, p. 5727 - 5729 (1967)
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Base-promoted ring expansion of 3-aminopyrimidine-2-thiones into 1,2,4-triazepine-3-thiones
Fesenko, Anastasia A.,Shutalev, Anatoly D.
supporting information, p. 2560 - 2573 (2016/04/26)
A base-promoted ring expansion of 3-amino-4-hydroxyhexahydropyrimidine-2-thiones into 2,4,5,6-tetrahydro-3H-1,2,4-triazepine-3-thiones has been developed. Experimental data and DFT calculations showed that the reaction proceeded through fast formation of intermediate acyclic isomers of pyrimidines followed by their slow cyclization into triazepines. The starting hydroxypyrimidines were prepared by reaction of α,β-unsaturated ketones or β-alkoxy ketones with HNCS followed by treatment of the obtained β-isothiocyanato ketones with hydrazine. Triazepine-3-thiones were transformed into their 3-oxo analogs by oxidation with H2O2 under basic conditions.
NEW DEVELOPMENTS OF THE WHARTON TRANSPOSITION
Dupuy, C.,Luche, J. L.
, p. 3437 - 3444 (2007/10/02)
The synthetically useful Wharton transposition can be improved by using a more adequate procedure in the critical step of the intermediate α-epoxyhydrazone cleavage.Either for stable hydrazones or unstable ones, the yield of the transposed allylic alcohol is increased by treatment under anhydrous conditions with highly basic reagents (KDA in the former case, NEt3 in the latter).
Reaction of Enamines with Acetals or Trialkyl Orthoformates Activated by Lewis Acids
Takazawa, Osamu,Kogami, Kunio,Hayashi, Kazuo
, p. 1876 - 1881 (2007/10/02)
Enamines, prepared readily from various carbonyl compounds, react with acetals or trialkyl orthoformates in the presence of Lewis acids such as BF3.OEt2 to give corresponding β-alkoxy carbonyl compounds or α-dialkoxymethyl carbonyl compounds in good yields.The reaction of dienamines with acetals or trialkyl orthoformates also selectively gives corresponding β,χ-unsaturated α-(α-alkoxyalkyl) carbonyl compounds or β,χ-unsatureted α-dialkoxymethyl carbonyl compounds in good yields.