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Paper | Special issue | Vol 42, No. 2, 1996, pp.625-634
Published online, 1st January, 1970
DOI: 10.3987/COM-95-S54
tert-Butylcyclopentane Derivatives. Part 8. Synthesis of tert-Butylcyclopentane-fused Pyrimidin-4-ones

Zsolt Szakonyi, Ferenc Fülöp, Gábor Bernáth, and Pál Sohár

*Institute of Pharmaceutical Chemistry, Albert Szent-Györgyi Medical University, H-6701 Szeged, Eötv¨øs u.6., Hungary


In the reactions of ethyl (1R*,2S*,4S*)-2-amino-4-tert-butyl-1-cyclopentanecarboxylate (4) or (1R*,3S*,5S*)-3-tert-butyl-6-azabicyclo[3.2.0]heptan-7-one (2) or (1R*,2S*,4S*)-2-amino-4-tert-butyl-1-cyclopentanecarboxamide (6) with imidates or triethyl orthobenzoate, tert-butylcyclopentane-fused dihydropyrimidin-4-ones (7a-e) were prepared. The azetidinone (2) with lactim ethers furnished pyrrolo-, pyrido- and azepino[1,2-a]pyrimidin-4-ones (8-10) in ringenlargement reactions. Ethyl (1R*,2S*,4S*)-2-amino-4-tert-butyl-1-cyclopentanecarboxylate (4) and ethyl (1R*,2S*,4S*)-2-benzylamino-4-tert-butyl-1-cyclopentanecarboxylate (5) and potassium cyanate or phenyl isocyanate or potassium thiocyanate or phenyl isothiocyanate, yielded pyrimidine-2,4-diones or 2-thioxopyrimidin-4-ones (11-22).