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-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.

cyclocondensation - acetonide cleavage - oxidative cleavage - heterocycles - pyrimidine derivatives

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Anisotropy of the protons of the endocyclic methylene group of the trans-isomer arises from different intramolecular interactions of the hydroxymethylene groups.