23893-30-3Relevant academic research and scientific papers
A new synthetic strategy towards 2,4,5-trisubstituted 1H-imidazoles and highly substituted pyrrolo[1,2-c]imidazoles by use of α-azidochalcones via Michael addition-cyclization followed by Wittig reaction
Adib, Mehdi,Peytam, Fariba,Rahmanian-Jazi, Mahmoud,Bijanzadeh, Hamid Reza,Amanlou, Massoud
, p. 6696 - 6705 (2017/10/25)
Efficient and facile protocols for the preparation of highly functionalized 1H-imidazoles and 5H-pyrrolo[1,2-c]imidazoles are described. Heating a mixture of an α-azidochalcones and N,N,N′,N′-tetramethyl guanidine under neat conditions gave the corresponding 2,4,5-trisubstituted 1H-imidazole via Michael addition-cyclization in excellent yields. Subsequently, the prepared 1H-imidazoles undergo addition-Wittig reaction with acetylenic esters in presence of triphenylphosphine in dichloromethane to afford 5H-pyrrolo[1,2-c]imidazoles in high yields.
Experimental and Theoretical Study of an Intramolecular CF3-Group Shift in the Reactions of α-Bromoenones with 1,2-Diamines
Muzalevskiy, Vasily M.,Ustynyuk, Yury A.,Gloriozov, Igor P.,Chertkov, Vyacheslav A.,Rulev, Alexander Yu.,Kondrashov, Evgeniy V.,Ushakov, Igor A.,Romanov, Alexey R.,Nenajdenko, Valentine G.
, p. 16982 - 16989 (2015/11/16)
The reactions of trifluoromethylated 2-bromoenones and N,N′-dialkyl-1,2-diamines have been studied. Depending on the structures of the starting compounds, the formation of 2-trifluoroacetylpiperazine or 3-trifluoromethylpiperazine-2-ones was observed. The mechanism of the reaction is discussed in terms of multistep processes involving sequential substitution of bromine in the starting α-bromoenones and intramolecular cyclization of the captodative aminoenones as key intermediates to form the target heterocycles. The results of theoretical calculations are in perfect agreement with the experimental data. The unique role of the trifluoromethyl group in this reaction is demonstrated.
Ecofriendly bromination of chalcones and synthesis of flavones using grinding technique
Jakhar, Komal,Makrandi
, p. 141 - 145 (2013/02/23)
Selective bromination of chalcones and 2'-hydroxychalcones has been carried out with ammonium bromide and ammonium persulphate using grinding technique at RT under aqueous moist condition to give α,β-dibromochalcones and α,β-dibromo-2'- hydroxychalcones respectively. α,β- Dibromo-2'-hydroxychalcones have been cyclodehydrobrominated with barium hydroxide moist and ethanol at RT to give flavones using grinding technique.
Poly(vinylpyrrolidone)-bromine complex; a mild and efficient reagent for selective bromination of alkenes and oxidation of alcohols
Lakouraj, Moslem Mansour,Tajbakhsh, Mahmood,Mokhtary, Masoud
, p. 481 - 483 (2007/10/03)
Poly(vinylpyrrolidone)-bromine complex (PVP-Br2) is easily prepared and used as a mild and convenient reagent for selective bromination of alkenes and at the position α-hydrogen of active carbonyl compounds. Selective oxidation of benzylic alcohols in the presence of aliphatic alcohols were also achieved at room temperature.
