A copper-catalyzed cascade reaction using isatins and amidine hydrochlorides for the synthesis of 2-(1,3,5-triazin-2-yl)aniline derivatives has been developed. This reaction features commercially available starting materials, mild reaction conditions and good functional group tolerance.
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Mechanistic Study of Asymmetric Alkynylation of Isatin-Derived Ketimine Mediated by a Copper/Guanidine Catalyst.
J Org Chem
September 2022
Key Laboratory of Green Chemistry and Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu, Sichuan 610064, P. R. China.
In this work, we performed a mechanistic study of asymmetric alkynylation of isatin-derived -Boc ketimine that was first reported by Feng, Liu, and co-workers ( , , 678-681). Guanidine-amide promoted the formation of highly nucleophilic copper acetylene species by abstracting the terminal proton of phenylacetylene with an imine moiety. The guanidinium salt-Cu(I) complex was the most active species in the addition of the C═N bond, in which copper acetylene coordinated to the O atom of the amide moiety, and the isatin-derived ketimine substrate was activated by hydrogen bonding as well as -butoxycarbonyl···Cu(I) coordination.
View Article and Find Full Text PDFSynthesis of Novel α-amidino Carboxylic Acids and their Use as H-Bond Catalysts in Strecker Reaction.
Comb Chem High Throughput Screen
August 2019
Department of Chemistry, Science and Research Branch, Islamic Azad University, Tehran, Iran.
Aim And Objective: A wide variety of synthesized amidine derivatives are bioactive compounds. They show a vast range of medical properties. Therefore, a simple route for synthesis of novel class of amidine derivatives called amidino carboxylic acids and their use as catalysts in Strecker reaction has been reported in the current work.
View Article and Find Full Text PDFCopper-catalyzed ambient-temperature decarboxylative annulation of isatins with amidine hydrochlorides: a facile access to 2-(1,3,5-triazin-2-yl)aniline derivatives.
Org Biomol Chem
June 2018
School of Chemistry and Environmental Engineering, Wuhan Institute of Technology, Wuhan 430073, China.
A copper-catalyzed cascade reaction using isatins and amidine hydrochlorides for the synthesis of 2-(1,3,5-triazin-2-yl)aniline derivatives has been developed. This reaction features commercially available starting materials, mild reaction conditions and good functional group tolerance.
View Article and Find Full Text PDFThe influence of substituents on the reactivity and cytotoxicity of imidazothiazolotriazinones.
Mol Divers
August 2018
N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Prosp., Moscow, Russian Federation, 119991.
A series of tetrahydroimidazo[4,5-e]thiazolo[3,2-b]-1,2,4-triazine-2,7(1H, 6H)-diones were synthesized via the reaction of imidazotriazinethiones and bromoacetic acid followed by condensation with isatins. Amidine skeletal rearrangement of 3,3a,9,9a-tetrahydroimidazo[4,5-e]thiazolo[3,2-b]-1,2,4-triazine-2,7 (1H, 6H)-diones into 1,3a,4,9a-tetrahydroimidazo[4,5-e]thiazolo[2,3-c]-1,2,4-triazine-2,8 (3H, 7H)-diones under KOH treatment has been studied. The influence of substituents at positions 1,3,3a,6,9a of imidazothiazolotriazine on the ability to undergo rearrangement was analyzed based on experimental data and theoretical calculations.
View Article and Find Full Text PDFDivergent Synthesis of Quinazolin-4(3H)-ones and Tryptanthrins Enabled by a tert-Butyl Hydroperoxide/K3PO4-Promoted Oxidative Cyclization of Isatins at Room Temperature.
Org Lett
June 2016
Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Hubei, Wuhan 430079, P. R. China.
A synergetic tert-butyl hydroperoxide/K3PO4-promoted oxidative cyclization has been developed for the facile synthesis of various functionalized quinazolin-4(3H)-ones from commercially available isatins and amidine hydrochlorides at room temperature. The synthetic utility of this strategy was illustrated by the convenient synthesis of tryptanthrin derivatives via a self-dimerization of isatins under the same conditions.
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