Novel Syntheses of Enantiopure Hexahydroimidazo[1,5-b]isoquinolines and Tetrahydroimidazo[1,5-b]isoquinolin-1(5H)-ones via Iminium Cation Cyclizations

Condensations of chiral diamines 11a−c with benzotriazole and formaldehyde gave benzotriazolyl intermediates 12a−c; similar condensations of α-amino-amides 10a−c with benzotriazole and paraformaldehyde gave 14a−c. Subsequent treatment of 12a−c and 14a−c with AlCl3 led to enantiopure tricyclic 1,2,3,...

Full description

Saved in:
Bibliographic Details
Published in:Journal of organic chemistry 2002-11, Vol.67 (23), p.8224-8229
Main Authors: Katritzky, Alan R, Suzuki, Kazuyuki, He, Hai-Ying
Format: Article
Language:English
Subjects:
Chemistry
Cyclization
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings
Imines
Inflammation Mediators - chemical synthesis
Isoquinolines - chemical synthesis
Organic chemistry
Preparations and properties
Stereoisomerism
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Condensations of chiral diamines 11a−c with benzotriazole and formaldehyde gave benzotriazolyl intermediates 12a−c; similar condensations of α-amino-amides 10a−c with benzotriazole and paraformaldehyde gave 14a−c. Subsequent treatment of 12a−c and 14a−c with AlCl3 led to enantiopure tricyclic 1,2,3,5,10,10a-hexahydroimidazo[1,5-b]isoquinolines 1a−c and 2,3,10,10a-tetrahydroimidazo[1,5-b]isoquinolin-1(5H)-ones 15a−c, respectively, via Lewis acid promoted iminium cation cyclizations.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo0203241