Solvent-Free C-3 Coupling of Azaindoles with Cyclic Imines

By direct coupling 7-azaindole and cyclic imines, such as 3,4-dihydroisoquinoline, 6,7-dihydrothieno[3,2-c]pyridine, 3,4-dihydro-beta -carboline, and 4,5-dihydro-3H-benz[c]azepine, new 3-substituted 7-azaindole derivatives have been synthesized. The reaction was extended to 4-azaindoles and 6-azaind...

Teljes leírás

Elmentve itt :
Bibliográfiai részletek
Szerzők: Belasri Khadija
Fülöp Ferenc
Szatmári István
Dokumentumtípus: Cikk
Megjelent: 2019
Sorozat:MOLECULES 24 No. 19
doi:10.3390/molecules24193578

mtmt:30963345
Online Access:http://publicatio.bibl.u-szeged.hu/17871
Leíró adatok
Tartalmi kivonat:By direct coupling 7-azaindole and cyclic imines, such as 3,4-dihydroisoquinoline, 6,7-dihydrothieno[3,2-c]pyridine, 3,4-dihydro-beta -carboline, and 4,5-dihydro-3H-benz[c]azepine, new 3-substituted 7-azaindole derivatives have been synthesized. The reaction was extended to 4-azaindoles and 6-azaindoles, as electron-rich aromatic compounds. The lowest reactivity was observed in the case of C-3 substitution of 5-azaindole. In this case, the aza-Friedel-Crafts reaction took place by using 10 mol % of p-toluenesulfonic acid (p-TSA) as the catalyst. The role of the acid catalyst can be explained by the different pKa values of the azaindoles. All reactions were performed in solvent-free conditions by using both classical heating and microwave irradiation. In all cases, microwave heating proved to be more convenient to synthesize new C-3-substituted azaindole derivatives.
Terjedelem/Fizikai jellemzők:Azonosító: 3578-Terjedelem: 10 p
ISSN:1420-3049