128668-89-3Relevant articles and documents
Saturated Heterocyles, 248. Synthesis of 2,4-Dioxo and 4-Oxo-2-thioxo Derivatives of Octahydrocyclopentapyrimidines
Fueloep, Ferenc,Szakonyi, Zsolt,Bernath, Gabor,Sohar, Pal
, p. 1211 - 1218 (2007/10/03)
Unsubstituted and 1-benzyl-substituted cis-cyclopentapyrimidine-2,4-diones and cis-2-thioxocyclopentapyrimidin-4-ones 9a,b and 10a,b were prepared from the corresponding cis-2-amino-1-cyclopentanecarboxylates 3 and 5 with potassium cyanate and thiocyanate.It was found that the cis-derivatives 7a-h readily underwent ring closure, resulting in 3-substituted cis-2,4-cyclopentapyrimidinediones and cis-2-thioxocyclopentapyrimidin-4-ones 11a-d and 12a-d, whereas the trans counterparts 8a-d failed to cyclize, but gave hydrolyzed amino acid derivatives 13a,b and 14.This difference in the reactivities of the cis and trans isomers is a further example of the difficulty of preparing cyclopentane trans-fused six-membered 1,3-heterocycles by ring closure.