REDUCTION AND CARBOXYLATION OF LOROMETHYG-6,7-DIMETHOXY-3,4-DIHYDROISOQUINOLINIUM SALTS - AN EASY ENTRY TO 1-HYDROXYMETHYL-1,2,3,4-TETRAHYDROISOQUINOLINE ALKALOIDS

Authors
SUAU R RUIZ I POSADAS N VALPUESTA M
Citation
R. Suau et al., REDUCTION AND CARBOXYLATION OF LOROMETHYG-6,7-DIMETHOXY-3,4-DIHYDROISOQUINOLINIUM SALTS - AN EASY ENTRY TO 1-HYDROXYMETHYL-1,2,3,4-TETRAHYDROISOQUINOLINE ALKALOIDS, Heterocycles, 43(3), 1996, pp. 545-550
Citations number
18
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Heterocycles → ACNP
ISSN journal
03855414
Volume
43
Issue
3
Year of publication
1996
Pages
545 - 550
Database
ISI
SICI code
0385-5414(1996)43:3<545:RACOL>2.0.ZU;2-H
Abstract
At 25 degrees C, the NaBH4/MeOH reduction of the title isoquinolinium salts gave the aziridine exclusively. At a low temperature (0 degrees C) in the presence of CO2/K2CO3, the 2-oxazolidinone was obtained in a lmost quantitative yield. Controlled hydrolysis of the borane complex derived from the isoquinolinium salts also gave the cyclic carbamate. (+/-)-Calycotomine and its N-Me derivative were obtained in high yield s.