Effective Synthesis of N-Alkyl-3-(Indol-3-yl)Pyrazoles from Ag2CO3-Catalyzed Regioselective Aza-Michael Addition of 5-(Indol-3-yl)-1HPyrazoles

Letters in Organic Chemistry, Journal Year: 2024, Volume and Issue: 21(10), P. 898 - 908

Published: March 12, 2024

Abstract: In this study, the synthesis of N-alkyl-3-(indol-3-yl)pyrazoles was carried out from Ag2CO3 catalyzed regioselective aza-Michael addition 5-(indol-3-yl)-1H-pyrazoles to α, β-unsaturated carbonyl compounds. presence 10 mol% Ag2CO3, reaction smoothly occurred in dichloroethane (DCE) at 120°C preferentially afford a series high yields with good regioselectivity. It found that 1-methyl-3-(3-methyl-1H-pyrazol-5-yl)-2-phenyl- 1H-indole, 1-benzyl-3-(3-methyl-1H-pyrazol-5-yl)-1H-indole, ketone, and β- unsaturated amide exclusively gave 3-(pyrazol-3-yl)indoles yields. This features regioselectivity, mild conditions, substrate scope yields, commercially available catalyst. Meanwhile, also proven be quite practical by gram-scale excellent

Language: Английский

---

Five-membered ring systems: With more than 1 N atom

Progress in heterocyclic chemistry, Journal Year: 2024, Volume and Issue: unknown, P. 211 - 257

Published: Jan. 1, 2024

Language: Английский

---