Direct Access to CF₃-Containing 4H-1,3-Oxazines and 2-Aminopyrimidines Via a [4 + 2] Annulation Using In Situ Generated Carbodiimide Anions

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

Published: March 11, 2025

The carbodiimide anions which were generated in situ from N-cyano-N-aryl-p-toluenesulfonamides (NCTS) the presence of base participated annulations that remain less reported to date. Herein, we have developed for first time an efficient and environmentally friendly [4 + 2] annulation reaction CF3-substituted hetero-1,3-dienes with NCTS synthesis 4H-1,3-oxazines 2-aminopyrimidines under transition-metal-free conditions. methodology demonstrates advantages readily available substrates, simple operation, good functional group tolerance, broad substrate scope, providing a promising route structurally diverse scaffolds. products followed by transformations provide facile TAS2R14 agonist analogues.

Language: Английский

Additive‐free and Diastereoselective Synthesis for trans‐Disubstituted‐2,3‐dihydro‐benzofurans via [4 + 1] Annulation between p‐QMs and TFISYs

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

Published: Oct. 14, 2024

Abstract An additive‐free and diastereoselective [4+1] annulation between ortho ‐hydroxyphenyl‐substituted para ‐quinone methides CF 3 ‐substituted imidoyl sulfoxonium ylides is developed, providing a facile practical route to diverse trans ‐2,3‐dihydrobenzofurans with high efficiency. This protocol features mild conditions, broad substrate scope easy operate.

Language: Английский