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Ruthenium catalyzes the synthesis of γ-butenolides fused with cyclohexanones
Thombal, Raju S.,Kim, Seoung-Tae,Baik, Mu-Hyun,Lee, Yong Rok The Royal Society of Chemistry 2019 Chemical communications Vol.55 No.20
<P>Ruthenium(II)-catalyzed reactions of cyclic diazodicarbonyl compounds with β-ketoamides for chemo- and stereoselective construction of cyclohexanone-fused γ-butenolides are described. This study represents the first example of the addition of an enol substrate which is formed by the tautomerization of the β-ketoamides to the electrophilic carbene center for unusual cyclization through amide cleavage. The combined experimental and computational studies shed light on the mechanistic pathway favouring the unusual ring formation reaction instead of the involvement of the general carbonyl ylide intermediates for the product generation.</P>
Thombal, Raju S.,Lee, Yong Rok American Chemical Society 2018 Organic letters Vol.20 No.15
<P>Indium(III)/silver(I)-catalyzed [2 + 2 + 1] annulation of arylhydrazine hydrochlorides with β-enamino esters via multicomponent reactions for the construction of diverse and multisubstituted <I>N</I>-arylpyrazoles has been demonstrated. The oxidative cycloaddition proceeds via a cascade triple Michael addition/elimination/air oxidation. This novel protocol provides a rapid and efficient synthetic route to various 3,4-diester-substituted <I>N</I>-arylpyrazoles. The synthesized compounds are further utilized for various synthetic transformations.</P> [FIG OMISSION]</BR>