Premium
Rapid Access to Polyfunctionalized 3,4‐Dihydroquinazolinones through a Sequential N ‐Acyliminium Ion Mannich Reaction Cascade
Author(s) -
Sawant Rajiv T.,
Stevens Marc Y.,
Odell Luke R.
Publication year - 2015
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.201501178
Subject(s) - chemistry , mannich reaction , amine gas treating , regioselectivity , functional group , combinatorial chemistry , alkyl , cascade , carbamate , cascade reaction , organic chemistry , catalysis , chromatography , polymer
A microwave‐promoted one‐pot, three‐component sequential cyclization‐Mannich reaction of unactivated ketones, o ‐formyl carbamates and primary amines has been developed. Cyclic N ‐acyliminium ions are generated in situ from the carbamate and amine starting materials. This metal‐free cascade protocol provides rapid access to structurally diverse 3,4‐dihydroquinazolinones in good to excellent yields with high regioselectivity for the terminal methyl group, in the case of unsymmetrical methyl alkyl ketones. Key features of the developed protocol include its operational simplicity, ease of product purification, and wide functional group tolerance.