(NHC)Cu-Catalyzed Mild C-H Amidation of (Hetero)arenes with Deprotectable Carbamates: Scope and Mechanistic Studies
Primary arylamines are an important unit broadly found in synthetic, biological, and materials science. Herein we describe the development of a (NHC)Cu system that mediates a direct C-H amidation of (hetero)arenes by using N-chlorocarbamates or their sodio derivatives as the practical amino sources. A facile stoichiometric reaction of reactive copper-aryl intermediates with the amidating reagent led us to isolate key copper arylcarbamate species with the formation of a C-N bond. The use of tBuONa base made this transformation catalytic under mild conditions. The present (NHC)Cu-catalyzed C-H amidation works efficiently and selectively on a large scale over a range of arenes including polyfluorobenzenes, azoles, and quinoline N-oxides. Deprotection of the newly installed carbamate groups such as Boc and Cbz was readily performed to afford the corresponding primary arylamines.
Xie, Weilong,Yoon, Jung Hee,Chang, Sukbok
supporting information
p. 12605 - 12614
(2016/10/07)
Synthesis of substituted benzo[d]thiazol-2-ylcarbamates as potential anticonvulsants
A series of substituted benzo[d]thiazol-2-ylcarbamates 4a-g and 5a-g were synthesized and evaluated for anticonvulsant activity. The structures of the synthesized compounds were confirmed on the basis of their physical and spectral data. The compounds were evaluated for anticonvulsant activity using PTZ-induced convulsion and maximal electroshock models. The target compounds have shown significant activity in these models.
Zinc promoted simple and convenient synthesis of carbamates: An easy access for amino group protection
Synthesis of alkyl, aryl, heterocyclic, carbohydrate and amino acid carbamates is described. The protection of the amino group in the presence of other functionality in amino acids demonstrates the importance of this method.
Yadav,Reddy, Gondi Sudershan,Reddy, M. Muralidhar,Meshram
p. 3259 - 3262
(2007/10/03)
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