Cyclocondensation of (±)-exo,exo-5,6-(Isopropylidenedioxy)-3-(pyrrolidinomethylene)bicyclo[2.2.1]heptan-2-one with N-C-N Dinucleophiles

ABSTRACT A number of protected 2-substituted 5,6,7,8-tetrahydro-5,8-methanoquinazoline-6,7-diols were prepared by condensation of amidines with (±)-EXO,EXO-5,6-(isopropylidenedioxy)-3-(pyrrolidinomethylene)bicyclo[2.2.1]heptan-2-one. Deprotection of the 2-phenyl derivative was followed by its one-po...

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Bibliographic Details
Published in:Synthesis (Stuttgart) 2007-05, Vol.2007 (9), p.1385-1391
Main Authors: Pérez-Castro, Isabel, Caamaño, Olga, García, Marcos D., Fernández, Franco, López, Carmen
Format: Article
Language:English
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Summary:ABSTRACT A number of protected 2-substituted 5,6,7,8-tetrahydro-5,8-methanoquinazoline-6,7-diols were prepared by condensation of amidines with (±)-EXO,EXO-5,6-(isopropylidenedioxy)-3-(pyrrolidinomethylene)bicyclo[2.2.1]heptan-2-one. Deprotection of the 2-phenyl derivative was followed by its one-pot transformation into a 1:1 mixture of (±)-CIS- and (±)-TRANS-2-phenyl-6,7-dihydro-5H-cyclopenta[D]pyrimidine-5,7-dimethanol by oxidative glycol cleavage and subsequent reduction with sodium borohydride.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-2007-965997