1051853-01-0Relevant articles and documents
Enantioselective Nickel-Catalyzed Alkyne-Azide Cycloaddition by Dynamic Kinetic Resolution
Liu, En-Chih,Topczewski, Joseph J.
supporting information, p. 5308 - 5313 (2021/05/04)
The triazole heterocycle has been widely adopted as an isostere for the amide bond. Many native amides are α-chiral, being derived from amino acids. This makes α-N-chiral triazoles attractive building blocks. This report describes the first enantioselective triazole synthesis that proceeds via nickel-catalyzed alkyne-azide cycloaddition (NiAAC). This dynamic kinetic resolution is enabled by a spontaneous [3,3]-sigmatropic rearrangement of the allylic azide. The 1,4,5-trisubstituted triazole products, derived from internal alkynes, are complementary to those commonly obtained by the related CuAAC reaction. Initial mechanistic experiments indicate that the NiAAC reaction proceeds through a monometallic Ni complex, which is distinct from the CuAAC manifold.
A direct and sustainable synthesis of tertiary butyl esters enabled by flow microreactors
Degennaro, Leonardo,Maggiulli, Daniela,Carlucci, Claudia,Fanelli, Flavio,Romanazzi, Giuseppe,Luisi, Renzo
supporting information, p. 9554 - 9557 (2016/08/01)
Tertiary butyl esters find large applications in synthetic organic chemistry. A straightforward method for the direct introduction of the tert-butoxycarbonyl group into a variety of organic compounds has been developed using flow microreactor systems. The resultant flow process was more efficient, versatile and sustainable compared to the batch.
Synthesis and structure-activity relationships of phenyl-substituted coumarins with anti-tubercular activity that target FadD32
Kawate, Tomohiko,Iwase, Noriaki,Shimizu, Motohisa,Stanley, Sarah A.,Wellington, Samantha,Kazyanskaya, Edward,Hung, Deborah T.
supporting information, p. 6052 - 6059 (2013/11/06)
In an effort to develop new and potent agents for therapy against tuberculosis, a high-throughput screen was performed against Mycobacterium tuberculosis strain H37Rv. Two 6-aryl-5,7-dimethyl-4-phenylcoumarin compounds 1a and 1b were found with modest activity. A series of coumarin derivatives were synthesized to improve potency and to investigate the structure-activity relationship of the series. Among them, compounds 1o and 2d showed improved activity with IC90 of 2 μM and 0.5 μM, respectively. Further optimization provided compound 3b with better physiochemical properties with IC90 0.4 μM which had activity in a mouse model of infection. The role of the conformation of the 4- and 6-aryl substituents is also described.
