Diphenylparabanic Acid as a Synthon for the Synthesis of α-Diketones and α-Ketocarboxylic Acids
…, M Hamano, S Todaka, T Asaeda, HK Ijuin…
Index: Watanabe, Nobuko; Hamano, Mitsutaka; Todaka, Shota; Asaeda, Takahiro; Ijuin, Hisako K.; Matsumoto, Masakatsu Journal of Organic Chemistry, 2012 , vol. 77, # 1 p. 632 - 639
Full Text: HTML
Citation Number: 2
Abstract
Diphenylparabanic acid was found to react with> 2 equiv of organolithiums at− 78° C to effectively give the corresponding symmetrical α-diketones. However, upon treatment with 1 equiv of organolithium, the parabanic acid gave mainly 5-substituted 5-hydroxyimidazolidine- 2, 4-diones. On the other hand, Grignard reagents were less reactive toward the parabanic acid at low temperature, and selectively gave the corresponding 5-hydroxyimidazolidine-2 ...
Related Articles:
Cleavage and some modifications of the 7-amide group of the cephamycins
[Shiozaki, Masao; Ishida, Noboru; Iino, Kimio; Hiraoka, Tetsuo Tetrahedron, 1980 , vol. 36, p. 2735 - 2740]
Manganese-catalyzed synthesis of hydantoin derivatives from terminal alkynes and isocyanates
[Kuninobu, Yoichiro; Kikuchi, Kou; Takai, Kazuhiko Chemistry Letters, 2008 , vol. 37, # 7 p. 740 - 741]
Chemistry of the adducts of N, N'-diphenylformamidine with oxalyl chloride and phosgene
[Barsa, E. A.; Richter, R. Journal of Organic Chemistry, 1986 , vol. 51, # 23 p. 4483 - 4485]
Urea cyclisation reaction studies
[Niddam, Valerie; Medou, Martial; Dessolin, Jean; Trabaud, Carole; Camplo, Michel; Kraus, Jean-Louis Journal of Heterocyclic Chemistry, 1997 , vol. 34, # 3 p. 829 - 833]
Reaction of oxalyl chloride and alkyloxalyl chlorides with isocyanates and isothiocyanates
[Richter, R.; Stuber, F. A.; Tucker, B. Journal of Organic Chemistry, 1984 , vol. 49, # 20 p. 3675 - 3681]