34192-86-4

Upstream product

• 644-34-8 (E)-3-(benzo[d][1,3]dioxol-5-yl)-1-phenylprop-2-en-1-one 
• 712-97-0 6-nitro-1,3-benzodioxole-5-carbaldehyde 
• 98-86-2 acetophenone 
• 1136-86-3 methyl (3,4,5-trimethoxyphenyl) ketone 
• 70-11-1 α-bromoacetophenone 
• 20913-05-7 (Benzoylmethylene)triphenylphosphorane 

Downstream Products

• 57489-86-8 6,7-(methylenedioxy)-2-phenylquinoline 
• 1262240-95-8 6-phenyl-[1,3]dioxolo[4,5-g]quinoline N-oxide 
• 34192-82-0 (5H-[1,3]dioxolo[4,5-f]indol-6-yl)(phenyl)methanone 

Relevant academic research and scientific papers

N2H4-H2O Enabled Umpolung Cyclization of o-Nitro Chalcones for the Construction of Quinoline N-Oxides

Umpolung is a unique strategy which converts the property of an atom into the opposite one. An efficient and general method for the construction of quinoline N-oxides via umpolung of carbonyl groups was developed from ortho-nitro chalcones and hydrazine i

Continuous Flow Synthesis of Quinolines via a Scalable Tandem Photoisomerization-Cyclization Process

A continuous photochemical process is presented that renders a series of quinoline products via an alkene isomerization and cyclocondensation cascade. It is demonstrated that a high-power LED lamp generates the desired targets with higher productivity and efficiency than a medium-pressure Hg-lamp. The scope of this tandem process is established and allows for the generation of various substituted quinolines in high yields and with throughputs of greater than one gram per hour. Finally, this effective flow process is coupled with a telescoped hydrogenation reaction to render a series of tetrahydroquinolines including the antimalarial natural product galipinine.

Indium-mediated reductive cyclization of 2-nitrochalcones to quinolines

The reductive cyclization of 2-nitrochalcones using indium in an aqueous alcohol solution containing ammonium chloride produced the corresponding quinolines in reasonable yields.{A figure is presented}.

A novel one-pot synthesis of 2-arylquinolines through cascade reactions mediated by samarium reagents

A novel one-pot synthesis of 2-arylquinolines 4 from onitrobenzaldehydes 1 and α-haloketones 2 through SmI3 and Sm (II) mediated cascade reactions is reported. The advantages of this new one-pot procedure are easily accessible substrates, simple and mild reaction conditions.

Synthesis of 2-Acyl- and 2-Benzoylindoles

2-Nitrobenzaldehydes (3a-c) on reaction with phosphoranes (4a and 4b), and triphenyl phosphine in refluxing diphenylether provide 2-acylindoles (6a-c) and 2-benzoylindoles (6d-f). Alternatively 2-nitrobenzaldehydes (3a-c) on reaction with phosphoranes (4a and 4b) give nitroketones (5a-f) which on refluxing with triphenyl phosphine in refluxing diphenyl ether furnish 2-acyl- and 2-benzoylindoles (6a-f).

PHARMACOLOGICALLY ACTIVE COMPOUNDS, METHODS FOR THE PREPARATION THEREOF AND COMPOSITIONS CONTAINING THE SAME

Pharmacologically active catechol derivatives of formula I I wherein R1 and R2 independently comprise hydrogen, alkyl, acyl, optionally substituted aroyl, lower alkylsulfonyl or alkylcabamoyl or taken together form a lower alkylidene or cycloalkylidene, X comprises an electronegative substituent such as halogen, nitro, cyano, lower alkylsulfonyl, sulfonamido, aldehyde, caboxyl or trifluoromethyl and R3 comprises hydrogen, halogen, hydroxy alkyl, amino, nitro, cyano, trifluoromethyl, lower alkylsulfonyl, sulfonamide, aldehyde, alkyl carbonyl, aralkylidene carbonyl or carboxyl or a group selected from wherein R4 comprises hydrogen, alkyl, cyano, carboxyl or acyl and R5 comprises hydrogen, cyano, carboxyl, alkoxycarbonyl, carboxyalkenyl, nitro, acyl, optionally substituted aroyl or heteroaroyl, hydroxyalkyl or carboxyalkyl or R4 and R5 together form a five to seven membered substituted cycloalkanone ring; -(CO)n(CH2)m-COR wherein n is 0-1 and m is 0-7 and R comprises hydroxy, alkyl, carboxyalkyl, optionally substituted alkene, alkoxy or optionally substituted amino; wherein R8 and R9 independently comprise hydrogen or one of the following optionally substituted groups; alkyl, alkenyl, alkynyl, cycloalkyl, aralkyl, or together form an optionally substituted piperidyl group; -NH-CO-R10 wherein R10 comprises a substituted alkyl group