Selective N-alkylation of isoquinolines, benzazepines and thienopyridines with aromatic aldehydes and naphthols Dedicated to the memory of Professor A. R. Katritzky
Abstract The reactions of 1- or 2-naphthol, benzaldehyde or substituted benzaldehydes with tetrahydroisoquinoline, tetrahydrobenzo[d]azepine, tetrahydrobenzo[c]azepine or tetrahydrothieno[3,2-c]pyridine under solvent-free conditions, allowed a series of tertiary aminonaphthols to be prepared. The re...
Elmentve itt :
| Szerzők: | |
|---|---|
| Dokumentumtípus: | Cikk |
| Megjelent: |
2015
|
| Sorozat: | TETRAHEDRON
71 No. 39 |
| doi: | 10.1016/j.tet.2015.03.011 |
| mtmt: | 2934139 |
| Online Access: | http://publicatio.bibl.u-szeged.hu/6004 |
| Tartalmi kivonat: | Abstract The reactions of 1- or 2-naphthol, benzaldehyde or substituted benzaldehydes with tetrahydroisoquinoline, tetrahydrobenzo[d]azepine, tetrahydrobenzo[c]azepine or tetrahydrothieno[3,2-c]pyridine under solvent-free conditions, allowed a series of tertiary aminonaphthols to be prepared. The reactions were accelerated by the use of microwave irradiation, and the yields were also improved. As an exception, the aminoalkylation of 2-naphthol with 1,2,3,4-tetrahydroisoquinoline in the presence of benzaldehyde led to the parallel N-alkylation and redox α-arylation of the tetrahydroisoquinoline in a ratio of 4:1. The reaction of 1-naphthol with 2,3,4,5-tetrahydro-1H-benzo[c]azepine led to the formation of the N-alkylated compound as a single product, illustrating that the reaction route depends on the structures of the cyclic amine and the naphthol. © 2015 Elsevier Ltd. |
|---|---|
| Terjedelem/Fizikai jellemzők: | 7216-7221 |
| ISSN: | 0040-4020 |