One-Pot Regioselective Synthesis of Spiroimidazolidinones via a Sequential Ugi 4CR/Azide-Isocyanide Coupling/Cyclization/Rearrangement/Hydroxylation Reaction

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

Published: Jan. 24, 2025

Herein a novel and robust methodology to spiroimidazolidinones has been developed under mild reaction. The reaction of (Z)-2-azido-3-phenylacrylic acids 1, aldehydes 2, amines 3, isocyanides 4, 6 produced regioselectively in 71–88% yields via sequential Ugi 4CR/Pd(0) catalyzed azide-isocyanide coupling/cyclization/rearrangement/hydroxylation Furthermore, the easily accessible starting materials, high bond-forming efficiency, broad substituent tolerance make this strategy useful synthetic medicinal chemistry.

Language: Английский

Diastereoselective Synthesis of Highly Functionalized γ‐Lactams via Ugi Reaction/Michael Addition

Chemistry - An Asian Journal, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 10, 2024

Abstract The γ‐lactam ring is a prominent feature in medicinal chemistry, and its synthesis has garnered significant interest due to valuable properties. Among the γ‐lactams, 2‐oxopyrrolidine‐3‐carbonitrile derivatives stand out as versatile synthons that can be readily transformed into variety of other functional groups. In this work, we successfully synthesized highly functionalized 3‐cyano‐2‐pyrrolidinones with moderate good overall yields using Ugi reaction followed by intramolecular Michael addition. process demonstrated excellent diastereoselectivity showed tolerance range isonitriles carbonyl compounds.

Language: Английский

Triflic-acid promoted post-Ugi condensation for the assembly of 2,6-diarylmorpholin-3-ones

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

A two-step one-pot synthesis of 2,6-diarylmorpholin-3-ones involving Ugi reaction followed by a triflic acid-promoted intramolecular condensation accompanied loss the isocyanide-originated amide moiety is described.

Language: Английский