Asymmetric induction in the reactions of azinones with C-nucleophiles

Abstract

Effect of acylating agents on the course of addition of C nucleophiles to 1,2,4 and 1,3,5 triazinones, as well as to quinoxalin 2(1H) one, was studied. A series of new azinone derivatives was obtained. A method for the preparation of diastereomerically pure addition products of indoles to 1,2,4 triazinones and quinoxalin 2(1H) one in the presence of N Ts L amino acid acyl chlorides was suggested.

New opportunities for the synthesis of quinoxaline derivatives

“…The synthesis of (2-oxo-1,2-dihydroquinoxalin-3-yl)methyl ketones in reaction of quinoxalin-2-one with ketones in dimethyl sulfate is described earlier [17]. 3-Indolyl derivative of quinoxalin-2-one was prepared from its reaction with indole in the presence of acylating reagents [30].…”

Monoimine Derived from trans-1,2-Diaminocyclohexane and Ethyl Glyoxylate: An Intermediate in Aza-Diels–Alder and Mannich Reactions

“…Quinoxalinones, imines containing a lactam functionality closely related to 6 , were applied in the Friedel–Crafts reaction to yield indolyl derivatives . Asymmetric induction was observed in the reaction of various azinones with nucleophiles . Diastereoselective Barbier allylation of dihydropyrazinones followed by cyclization afforded chiral bicyclic and tricyclic piperazinones .…”

“…13 Asymmetric induction was observed in the reaction of various azinones with nucleophiles. 14 Diastereoselective Barbier allylation of dihydropyrazinones followed by cyclization afforded chiral bicyclic and tricyclic piperazinones. 15 In conclusion, the stereoselective addition of pyrrole and furan to bicyclic imine under Diels−Alder conditions described herein (see Scheme 2) provides an interesting route to new chiral heterocyclic compounds, which will be tested as (N,X)donating ligands for asymmetric catalysis.…”