Journal of Organic Chemistry p. 477 - 481 (1989)
Update date:2022-08-04
Topics:
Fang, Jim-Min
Yang,Chau-Chen
Wang, Yu-Wen
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 chlorosulphonyl isocyanate.The diarylmethylamines 8-10, generated by cycloaddition of α-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-1-methylindole.
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