A simple approach for the regioselective synthesis of imidazo[1,2- a]pyrimidiones and pyrimido[1,2- a]pyrimidinones

Several imidazo and pyrimido[1,2- a]pyrimidinones of type 1 and 2 were synthesized through intramolecular cyclization of pyrimidines 9 or pyrimidinones 10 bearing a variety of β and γ-aminoalcohols at the 2-position. Ring closure of the pyrimidinones of type 10 under Mitsunobu conditions lead to mix...

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Bibliographic Details
Published in:Tetrahedron 2006-02, Vol.62 (7), p.1433-1443
Main Authors: Font, David, Linden, Anthony, Heras, Montserrat, Villalgordo, José M.
Format: Article
Language:English
Subjects:
Acidic hydrolysis
Imidazo[1,2- a]pyrimidinone
ipso-Substitution
Mitsunobu reaction
Pyrimido[1,2- b]pyrimidinone
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Summary:Several imidazo and pyrimido[1,2- a]pyrimidinones of type 1 and 2 were synthesized through intramolecular cyclization of pyrimidines 9 or pyrimidinones 10 bearing a variety of β and γ-aminoalcohols at the 2-position. Ring closure of the pyrimidinones of type 10 under Mitsunobu conditions lead to mixtures of both bicyclic regioisomers 1 and 2 . Treatment of pyrimidines of type 9 with H 2SO 4 provided an efficient and operationally simple one-pot hydrolysis–cyclization procedure for obtaining imidazo and pyrimido[1,2- a]pyrimidinones 1 in good yields as the sole regioisomeric bicyclic product. Graphical Abstract
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2005.11.014