126401-65-8Relevant articles and documents
Formamides as Isocyanate Surrogates: A Mechanistically Driven Approach to the Development of Atom-Efficient, Selective Catalytic Syntheses of Ureas, Carbamates, and Heterocycles
Bruffaerts, Jeffrey,Von Wolff, Niklas,Diskin-Posner, Yael,Ben-David, Yehoshoa,Milstein, David
supporting information, p. 16486 - 16493 (2019/10/14)
Despite the hazardous nature of isocyanates, they remain key building blocks in bulk and fine chemical synthesis. By surrogating them with less potent and readily available formamide precursors, we herein demonstrate an alternative, mechanistic approach to selectively access a broad range of ureas, carbamates, and heterocycles via ruthenium-based pincer complex catalyzed acceptorless dehydrogenative coupling reactions. The design of these highly atom-efficient procedures was driven by the identification and characterization of the relevant organometallic complexes, uniquely exhibiting the trapping of an isocyanate intermediate. Density functional theory (DFT) calculations further contributed to shed light on the remarkably orchestrated chain of catalytic events, involving metal-ligand cooperation.
Ring Cleavage Reaction of 1,3-Oxazine-2,4(3H)-dione Derivatives with Amines
Kinoshita, Toshio,Takeuchi, Kozue,Kondoh, Masaya,Furukawa, Sunao
, p. 2026 - 2029 (2007/10/02)
The reactions of 3,6-dimethyl -1,3-oxazine-2,4(3H)-diones (1a, 1b, and 1c) with various amines were investigated under various conditions.Several reactions products were obtained such as the pyrimidines (3a, 3b, 3c, and 3d), the acetoacetamides (4a, 4b, and 4c), (4-chlorophenyl)urethane (5a), and ethyl acetoacetate (4d) with primary amines, and the acetoacetamides (4e and 4f), the urethanes (5a and 5b), the carboxamides (5c, 5d, 5e, and 5f), and the butenamides (7a, 7b, and 7c) with secondary amines.In the case of 1c with amine, alcohol used as a solvent reacted as a nucleophile to give the urethane (5a or 5b).
