Bischler-Napieralski cyclization of N-[2-(2-bromo-5-hydroxy-4-methoxyphenyl)ethyl]-N-[(S)-1-phenylethyl]-2-(2-bromo-4,5-dimethoxyphenyl)acetamide accompanied by elimination of chiral auxiliary

Authors
Miyatani, K Ohno, M Tatsumi, K Ohishi, Y Kunitomo, J Kawasaki, I Yamashita, M Ohta, S
Citation
K. Miyatani et al., Bischler-Napieralski cyclization of N-[2-(2-bromo-5-hydroxy-4-methoxyphenyl)ethyl]-N-[(S)-1-phenylethyl]-2-(2-bromo-4,5-dimethoxyphenyl)acetamide accompanied by elimination of chiral auxiliary, HETEROCYCLE, 55(3), 2001, pp. 589-595
Citations number
22
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
HETEROCYCLES
ISSN journal
03855414 → ACNP
Volume
55
Issue
3
Year of publication
2001
Pages
589 - 595
Database
ISI
SICI code
0385-5414(20010301)55:3<589:BCON>2.0.ZU;2-B
Abstract
N-[2-(2-Bromo-5-hydroxy-4-methoxyphenyl)ethyl]-N-[(S)-1-phenylethyl]-2-(2-b romo-4,5-dimethoxyphenyl)acetamide (5) was cyclized under N-dealkylation at the 2-position to the racemic 1-benzyl-1,2,3,4 tetrahydroisoquinoline deri vatives (6) by the Bischler-Napieralski cyclization followed by NaBH4 reduc tion (Polniaszek's method).