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Transition‐Metal‐Catalyzed Hydroamination and Carboamination Reactions of Anthranilic Allenamides as a Route to 2‐Vinyl‐ and 2‐(α‐Styryl)quinazolin‐4‐one Derivatives
Author(s) -
Broggini Gianluigi,
Borsini Elena,
Fasana Andrea,
Poli Giovanni,
Liron Frédéric
Publication year - 2012
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201200353
Subject(s) - hydroamination , chemistry , anthranilic acid , intramolecular force , catalysis , isomerization , palladium , amination , combinatorial chemistry , organic chemistry
2‐Vinyl‐ and 2‐(α‐styryl)quinazolin‐4‐ones have been synthesized by intramolecular gold‐catalyzed hydroamination and palladium‐catalyzed carboamination of anthranilic allenamides, easily prepared by prototropic isomerization of the corresponding propargylamides. These procedures, which lead to N ‐Boc‐protected quinazolinones, represent a more flexible alternative to the reported palladium‐catalyzedamination of anthranilic allylamides, achievable only from N ‐tosylallylamides.