Arif M. Ismiyev, A. Maharramov, R. Aliyeva
Jan 30, 2013
Citations
0
Influential Citations
8
Citations
Journal
Journal of Molecular Structure
Abstract
Abstract The condensation of diethyl 4-hydroxy-4-methyl-6-oxo-2-(4-substitutedphenyl)-cyclohexane-1,3-dicarboxylates and N′-(2-chloropropyl)ethane-1,2-diamine leads to diethyl 1-(2-chloropropyl)-9-hydroxy-9-methyl-7-phenyl-1,4-diazaspiro[4.5]decane-6,8-dicarboxylate ( 2 ) and its para -substituted methyl ( 1 ), chloro ( 3 ), bromo ( 4 ), and nitro ( 5 ) derivatives with a new stereogenic center, which were fully characterized by elemental analysis, ESI-MS, IR, 1 H and 13 C NMR spectroscopies and X-ray single-crystal analysis (for 2 ). The condensation reaction is regioselective, only cyclohexanone carbonyl moiety undergoes the transformation, leaving the β-keto ester carbonyls unreacted. Withing the compounds 1 – 5 , the increase in the Hammett’s σ p , related normal σ p n , inductive σ I , negative σ p - and positive σ p + polar conjugation and Taft’s σ p o substituent constants generally leads to the corresponding drift of δ O H and δ N H NMR chemical shifts to lower field.