Synthesis of isoquinoline alkaloid, (+/-)-salsolidine, using thiazolino[2,3-a]isoquinolinone S-oxide as intermediate

Authors
Rozwadowska, MD Sulima, A
Citation
Md. Rozwadowska et A. Sulima, Synthesis of isoquinoline alkaloid, (+/-)-salsolidine, using thiazolino[2,3-a]isoquinolinone S-oxide as intermediate, POL J CHEM, 75(12), 2001, pp. 1847-1852
Citations number
22
Categorie Soggetti
Chemistry
Journal title
POLISH JOURNAL OF CHEMISTRY
ISSN journal
01375083 → ACNP
Volume
75
Issue
12
Year of publication
2001
Pages
1847 - 1852
Database
ISI
SICI code
0137-5083(200112)75:12<1847:SOIA(U>2.0.ZU;2-F
Abstract
Thiazolino[2,3-a] isoquinlinones have been oxidized to the corresponding S- oxides and their I Ob-methyl derivatives desulfurized with Raney nickel to give (+/-) N-acyl salsolidine. Base-catalyzed hydrolysis of the N-acetyl de rivative afforded (+/-)-salsolidine. C-Methylation reactions of the title h eterocyclic system have been investigated throughly. Stereochemistry of the synthesized compounds has been established.