Concomitant (3 + 3) Annulation/Fragmentation of Triazinanes with Enamines: Electrosynthesis of Multisubstituted Dihydropyrimidines

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: March 6, 2025

An electro-oxidative formal (3 + 3) annulation of 1,3,5-triazinanes with enamines toward multisubstituted 1,2-dihydropyrimidines is reported. This metal-free mild protocol offers wide functional group tolerance, and heterocycles an unexplored molecular scaffold were constructed in excellent yields. Mechanistically, the electro-oxidation triazinane nucleophilic reactivity enamine result a concomitant annulation-fragmentation process, leading to six-membered heterocyclic product.

Language: Английский

Divergent Sc(OTf)3‐Catalyzed Tandem Cyclization of o‐Hydroxyphenyl Enaminones with 1,3,5‐Triazinanes: Access to C3‐Aminomethyl Chromones and Tetrahydropyrimidines

Asian Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 9, 2024

Abstract A Sc(OTf) 3 ‐catalyzed tandem cyclization reaction of o ‐hydroxyphenyl enaminones with 1,3,5‐triazinanes has been developed to generate two distinct annulated products in moderate good yields, which is dominated by the electronic characteristics 1,3,5‐triazinanes. The 1,3,5‐triaryl‐1,3,5‐triazinane reacted as C−N synthon produce C3‐aminomethyl chromone, while 1,3,5‐trialkyl‐1,3,5‐triazinane acted C−N−C−N synthons deliver N , ‐dialkyl tetrahydropyrimidine a free hydroxyl group.

Language: Английский