3066-44-2Relevant articles and documents
Benzylic C-H isocyanation/amine coupling sequence enabling high-throughput synthesis of pharmaceutically relevant ureas
Krska, Shane W.,Lin, Shishi,Nkulu, Leah E.,Stahl, Shannon S.,Suh, Sung-Eun
, p. 10380 - 10387 (2021/08/12)
C(sp3)-H functionalization methods provide an ideal synthetic platform for medicinal chemistry; however, such methods are often constrained by practical limitations. The present study outlines a C(sp3)-H isocyanation protocol that enables the synthesis of diverse, pharmaceutically relevant benzylic ureas in high-throughput format. The operationally simple C-H isocyanation method shows high site selectivity and good functional group tolerance, and uses commercially available catalyst components and reagents [CuOAc, 2,2′-bis(oxazoline) ligand, (trimethylsilyl)isocyanate, andN-fluorobenzenesulfonimide]. The isocyanate products may be used without isolation or purification in a subsequent coupling step with primary and secondary amines to afford hundreds of diverse ureas. These results provide a template for implementation of C-H functionalization/cross-coupling in drug discovery.
N-methylimidazole-catalyzed synthesis of carbamates from hydroxamic acids via the lossen rearrangement
Yoganathan, Sabesan,Miller, Scott J.
, p. 602 - 605 (2013/04/11)
An efficient, one-pot, N-methylimidazole (NMI) accelerated synthesis of aromatic and aliphatic carbamates via the Lossen rearrangement is reported. NMI is a catalyst for the conversion of isocyanate intermediates to the carbamates. Moreover, the utility of arylsulfonyl chloride in combination with NMI minimizes the formation of often-observed hydroxamate-isocyanate dimers during the sequence. Under the present conditions, lowering of temperatures is also possible, enabling a mild protocol.
Triphenylphosphine/2,3-dichloro-5,6-dicyanobenzoquinone (DDQ)/[n-Bu4N]OCN as a useful system for the efficient conversion of tetrahydropyranyl (THP) ethers to the corresponding alkyl isocyanates
Akhlaghinia, Batool,Samiei, Sima
experimental part, p. 2525 - 2529 (2010/03/31)
Triphenylphosphine/2,3-dichloro-5,6-dicyanobenzoquinone/tetrabutylammonium cyanate was used as an efficient system for the conversion of tetrahydropyranyl ethers to the corresponding alkyl isocyanates. Taylor & Francis Group, LLC.
