32998-26-8Relevant academic research and scientific papers
Development of an unexpected reaction pathway for the synthesis of 1,2,4-trisubstituted pyrrolo[1,2-a]quinoxalines through palladium-catalyzed cascade reactions
Keivanloo, Ali,Soozani, Atena,Bakherad, Mohammad,Mirzaee, Mahdi,Rudbari, Hadi Amiri,Bruno, Giuseppe
, p. 1633 - 1639 (2017/03/08)
1,2,4-trisubstituted pyrrolo[1,2-a]quinoxalines are synthesized through the multi-component reaction of 3-substituted 2-chloroquinoxalines, propargyl bromide, and excess secondary amines in the presence of a palladium copper catalytic system. This one-pot process provides an unexpected synthesis of new trisubstituted pyrrolo[1,2-a]quinoxalines by the introduction of two amine substituents onto the fused pyrrole rings in a single reaction procedure. The compounds formed are fully characterized by the analytical spectral data and X-ray analysis. A number of synthesized pyrrolo[1,2-a]quinoxaline derivatives are also screened against the three bacterial strains Micrococcus luteus, Pseudomonas aeruginos, and Bacillus subtilis. According to the results obtained, compounds 3b, 3c, and 3e are active against M.?luteus, compounds 3b and 3e are active against Ps. Aeruginos, and only compound 3f is active against all the three bacterial strains.
Novel multi-component synthesis of 1,4-disubstituted pyrrolo[1,2-a]quinoxalines through palladium-catalyzed coupling reaction/hetero-annulation in water
Keivanloo, Ali,Kazemi, Shaghayegh Sadat,Nasr-Isfahani, Hossein,Bamoniri, Abdolhamid
supporting information, p. 6536 - 6542 (2016/09/23)
1,4-Disubstituted pyrrolo[1,2-a]quinoxalines were prepared through the one-pot multi-component reactions of 3-substituted-2-chloroquinoxalines, propargyl alcohol, and secondary amines, catalyzed by Pd/Cu, in the presence of K2CO3and sodium dodecyl sulfate (SDS) in water. This process provided a facile, eco-friendly, and highly efficient method for the synthesis of new pyrrolo[1,2-a]quinoxalines in water with good yields.
NUCLEOPHILIC SUBSTITUTIONS ON 2-CHLORO-3-NITROQUINOXALINE
Nasielski-Hinkens, R.,Kaisin, M.,Grandjean, D.,Loos, M.,Nasielski, J.
, p. 919 - 926 (2007/10/02)
Piperidine, cyclohexylamine, methoxide ion and para-thiocresolate ion react with 2-chloro-3-nitroquinoxaline 1 by selectively substituting the nitro group, in contrast to be behavior of most ortho-chloronitroaromatics which loose halide when subjected to nucleophilic substitution reactions.This inversion is interpreted as being due to the lack of activation of the 2-position by the nitro group in the 3-position because of the low value of the ?-bond index between these two vertices.It is also suggested that the substitution by neutral reagents such as amines is strongly influenced by stabilizing interactions between the negatively charged nitro group and the ammonium moiety in the ? complex; this built-in solvation may be responsible for inversions in the chemoselectivity between chloro and nitro nucleofugicities.
