158432-46-3Relevant academic research and scientific papers
Synthesis of tetrahydro-2(1H)quinazolinones, cyclopenta[d]-2(1H) pyrimidinones, and their thioxo analogs from 2-trifluoroacetyl-1- methoxycycloalkenes
Bonacorso, Helio G.,Costa, Michelle B.,Lopes, Itamar S.,Oliveira, Marli R.,Drekener, Roberta L.,Martins, Marcos A. P.,Zanatta, Nilo,Flores, Alex F. C.
, p. 3055 - 3064 (2007/10/03)
A series of six (8)-alkyl-4-trifluoromethyl-5,6,7,8-tetrahydro-2(1 H)quinazolinones, 4-trifluoromethyl-cyclopenta[d]-2(1 H)pyrimidinones, and their thioxo analogs from the reaction of five β-alkoxyvinyl trifluoromethyl ketones, derived from alkylated cyclohexanones and cyclopentanone with urea and thiourea, is reported. The reactions were carried out in a single step in propan-2-ol as solvent and boron trifluoride diethyl etherate as catalyst in 18-65% yield. Copyright Taylor & Francis, Inc.
Synthesis, 17O NMR spectroscopy and structure of 2-trifluoroacetyl-1-methoxycycloalkenes
Bonacorso, Helio G.,Costa, Michelle B.,Moura, Sidnei,Pizzuti, Lucas,Martins, Marcos A.P.,Zanatta, Nilo,Flores, Alex F.C.
, p. 1396 - 1402 (2007/10/03)
Among the synthesis of a series of five well-known 2-trifluoroacetyl-1- methoxycycloalkenes derived from cyclopentanone and substituted cyclohexanones, this paper describes the synthesis of three new 2-trifluoroacetyl-1- methoxycycloalkenes derived from cycloheptanone, cyclooctanone and cyclododecanone in 60-68% yield. Subsequently, the 17O NMR chemical shift analysis of the carbonyl and the methoxy groups for these cyclic molecules clearly showed the electron push-pull phenomenon and revealed large and irregular variations of 17O NMR chemical shifts with the ring size. Finally, a more stable conformation of these trifluoroacetyl-containing cycloalkenes was determined by energy minimization calculations using Austin Model 1 (AM1) semi-empirical method and correlations between 17O NMR data and torsion angles or oxygen net charge calculated by AM1 semi-empirical method were performed.
