41957-65-7Relevant academic research and scientific papers
Catalytic arylation of a C-H bond in pyridine and related six-membered N-heteroarenes using organozinc reagents
Hyodo, Isao,Tobisu, Mamoru,Chatani, Naoto
supporting information; experimental part, p. 1357 - 1365 (2012/08/08)
Despite significant advances in the catalytic direct arylation of heteroarenes, the application of this reaction to pyridines has been met with limited success. An oxidative nucleophilic arylation strategy has been developed to overcome this problem. Pyridine, pyrazine, quinolone, and related electron-deficient N-heteroarenes can be arylated at the most electrophilic site using the developed nickel-catalyzed reaction. This protocol serves as a complementary method to catalytic direct arylation reactions. Less is more: Pyridine, pyrazine, quinoline and related electron-deficient N-heteroarenes can be arylated at the most electrophilic site using organozinc reagents through nickel catalysis. This protocol serves as a complementary method to catalytic direct arylation reactions. Copyright
One-pot friedlnder quinoline synthesis: Scope and limitations
Li, An-Hu,Beard, David J.,Coate, Heather,Honda, Ayako,Kadalbajoo, Mridula,Kleinberg, Andrew,Laufer, Radoslaw,Mulvihill, Kristen M.,Nigro, Anthony,Rastogi, Pawan,Sherman, Dan,Siu, Kam W.,Steinig, Arno G.,Wang, Ti,Werner, Doug,Crew, Andrew P.,Mulvihill, Mark J.
experimental part, p. 1678 - 1686 (2010/06/22)
A highly effective one-pot Friedlnder quinoline synthesis from o-nitroarylcarbaldehydes and ketones or aldehydes was developed and the scope and limitations of the method were examined. The o-nitroarylcarbaldehydes were reduced to o-aminoarylcarbaldehydes with iron in the presence of a catalytic amount of aqueous hydrochloric acid; the amino compounds were then condensed in situ with ketones or aldehydes to form mono- or disubstituted quinolines, respectively, in good-to-excellent yields (58-100%). Georg Thieme Verlag Stuttgart - New York.
A highly effective one-pot synthesis of quinolines from o-nitroarylcarbaldehydes
Li, An-Hu,Ahmed, Eilaf,Chen, Xin,Cox, Matthew,Crew, Andrew P.,Dong, Han-Qing,Jin, Meizhong,Ma, Lifu,Panicker, Bijoy,Siu, Kam W.,Steinig, Arno G.,Stolz, Kathryn M.,Tavares, Paula A. R.,Volk, Brian,Weng, Qinghua,Werner, Doug,Mulvihill, Mark J.
, p. 61 - 64 (2008/03/14)
A simple and an efficient one-pot quinoline synthesis using inexpensive and readily available reagents was proposed. The solids were removed by filtration and the filtrate was treated with ketone and powdered KOH. The o-Nitroarylcarbaldehydes were reduced to aminocarbaldehydes with iron in the presence of catalytic HCl and subsequently condensed in situ with aldehydes or ketones to form mono- or di-substituted quinolines in high yields. The method can be used to prepare 2,3-disubstituted quinolines. A mixture of isomers was generated when an unsymmetrical ketone was used, which proved to be easily separable by silica gel column chromatography. The one-pot procedure is mild enough to allow a phenyl-substituted α,β-unsaturated ketone for using as a reactant under basic conditions in refluxing ethanol without significant competition from 1,4-Michael addition. The method provides efficient means to synthesize biologically active natural and unnatural quinoline-derived compounds.
