A simple approach for the regioselective synthesis of imidazo[1,2-a]pyrimidiones and pyrimido[1,2-a]pyrimidinones |
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| Authors: | David Font Montserrat Heras José M Villalgordo |
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| Institution: | a Department of Chemistry, Faculty of Sciences, University of Girona, Campus de Montilivi, 17071 Girona, Spain
b Institute of Organic Chemistry, University of Zürich, Winterthurerstrasse 190, CH-8057 Zürich, Switzerland |
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| Abstract: | Several imidazo and pyrimido1,2-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 H2SO4 provided an efficient and operationally simple one-pot hydrolysis-cyclization procedure for obtaining imidazo and pyrimido1,2-a]pyrimidinones 1 in good yields as the sole regioisomeric bicyclic product. |
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| Keywords: | Imidazo[1 2-a]pyrimidinone Pyrimido[1 2-b]pyrimidinone Mitsunobu reaction ipso-Substitution Acidic hydrolysis |
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