51409-82-6Relevant academic research and scientific papers
Iodine(III)-Promoted Ring Contractive Cyanation of Exocyclic β-Enaminones for the Synthesis of Cyanocyclopentanones
Bhattacherjee, Dhananjay,Thakur, Vandna,Sharma, Saurabh,Kumar, Sandeep,Bharti, Richa,Reddy, C. Bal,Das, Pralay
supporting information, p. 2209 - 2214 (2017/07/07)
A highly efficient hypervalent iodine-promoted regiocontrolled ring contractive cyanation (RCC) reaction of exocyclic β-enaminones for the synthesis of cyanocyclopentanone (CCP) was demonstrated at ambient temperature with a wide substrate scope. The meth
Hypervalent Iodine-Promoted Aromatization of Exocyclic β-Enaminones for the Synthesis of meta-N,N-Diarylaminophenols
Bhattacherjee, Dhananjay,Thakur, Vandna,Shil, Arun K.,Das, Pralay
supporting information, p. 2202 - 2208 (2017/07/07)
A metal- and additive-free milder cascade approach for the synthesis of meta-N,N-diarylaminophenols (DAAP) starting from exocyclic β-enaminones has been developed. The feasibility of the process is rationalized by the suitable molecular geometry of β-enaminones for tandem N-arylative α-iodination and aromatization under milder basic conditions. Furthermore, the developed strategy has been extended to the synthesis of meta-N-benzyl-N-arylaminophenols (BAAP). 4-Ethylpropionyl-2-cyclohexenone has been explored to give 7-diarylaminochroman-2-one (DAAC) by employing a similar one-pot approach. The plausible mechanistic steps were deduced based upon isolation of a stable intermediate and structural identification through X-ray crystallographic analysis. (Figure presented.).
NMR of enaminones part 3 ? - 1H, 13C and 17O NMR spectroscopic studies of acyclic and cyclic N-aryl enaminones: Substituent effects and intramolecular hydrogen bonding
Zhuo, Jin-Cong
, p. 311 - 322 (2007/10/03)
17O, 13C and 1H NMR spectra for para-and meta-substituted 4-arylaminopent-3-en-2-ones (acyclic enaminones, 1 and 2) and 3-arylaminocyclohex-2-en-1-ones (cyclic enaminones, 3 and 4) are reported. The 17O, 13C and 1H shift values of these enaminones correlate well with σm0 and σp- constants in the correlations for meta and para derivatives, and with pKa values of the corresponding anilines. Dual substituent parameters analyses were also performed. Correlations of 17O and 13C chemical shifts of the carbonyl groups with those of the corresponding N-acylanilines indicate that the enaminone moiety as a whole has electronic properties similar to those of the RCONH group. The 17O shift values of the carbonyl O atoms of enaminones correlate well with their 1H and 13C data. Shieldings of 33-45 ppm for O atoms are observed for 1 and 2 compared with 3 and 4, respectively. This is attributed to intramolecular hydrogen bonding.
