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

✍ Scribed by Helmi Hussain; Ebrahim Kianmehr; Tony Durst

Book ID: 104230207
Publisher: Elsevier Science
Year: 2001
Tongue: French
Weight: 112 KB
Volume: 42
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)00130-7

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✦ Synopsis

Reaction of the azaallyllithiums derived from imines of a-amino esters with benzynes results in the formation of 1,3-dihydroisoindoles and 4-hydroxyisoquinolines via 3+2 and 2+2 cycloadditions, respectively. The initially formed 1-carboethoxy-1,3-dihydroisoindoles rearrange under basic reaction conditions to form 3-(2H)-isoquinolinones.

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