Use of α-Anilino Dienenitriles as Nucleophiles in Cycloadditions
Resource
Journal of Organometallic Chemistry, v.54, p.477-481
Journal
Journal of Organometallic Chemistry
Journal Volume
v.54
Pages
477-481
Date Issued
1989
Date
1989
Author(s)
Abstract
The α-anilino dienenitriles 1–5 were prepared. The dienes 1–3 reacted with dichlorocarbene and electrophiles containing electron-deficient double bonds such as maleic anhydride, benzoquinone, dimethyl acetylenedicarboxylate, tetracyanoethylene, and chlorosulfonyl isocyanate. The diarylmethylamines 8–10, generated by cycloaddition of a-anilino dienenitriles and maleic anhydride, were successfully transformed into acridones 15–17. Intramolecular cyclization of trienes 4 and 5 yielded the carbazoles and dihydro derivatives, accompanied by formation of 2-cyano-l-methylindole. © 1989, American Chemical Society. All rights reserved.
Type
journal article