Competitive 3+2 and 2+2 cycloadditions of ester stabilized azaallyl anionsto benzynes. Ring expansion of initial 3+2 products to isoquinolin-3-ones

Authors
Hussain, H Kianmehr, E Durst, T
Citation
H. Hussain et al., Competitive 3+2 and 2+2 cycloadditions of ester stabilized azaallyl anionsto benzynes. Ring expansion of initial 3+2 products to isoquinolin-3-ones, TETRAHEDR L, 42(12), 2001, pp. 2245-2248
Citations number
11
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
42
Issue
12
Year of publication
2001
Pages
2245 - 2248
Database
ISI
SICI code
0040-4039(20010318)42:12<2245:C3A2CO>2.0.ZU;2-8
Abstract
Reaction of the azaallyllithiums derived from imines of alpha -amino esters with benzynes results in the formation of 1,3-dihydroisoindoles and 4-hydr oxyisoquinolines via 3+2 and 2+2 cycloadditions, respectively. The initiall y formed 1-carboethoxy-1,3-dihydroisoindoles rearrange under basic reaction conditions to form 3-(2H)-isoquinolinones. (C) 2001 Published by Elsevier Science Ltd.