30490-54-1Relevant academic research and scientific papers
A simple way to some sophisticated fused nitrogen heterocycles
Wróbel, Zbigniew
, p. 1929 - 1932 (2004)
Selected nitroarenes were found to react with arylmethylene compounds prone to form benzylic-type carbanion to give fused nitrogen heterocycles in the presence of silylating agent.
Efficient formation of σH-adducts as a key step in the synthesis of acridines via Lewis acid-promoted transformations of the nitro group
Bobin, Mariusz,Kwast, Andrzej,Wróbel, Zbigniew
, p. 11048 - 11054 (2008/02/12)
A step-by-step methodology was applied in the Lewis acid-promoted synthesis of fused heterocyclic systems from carbanions and nitroarenes. Efficient formation of σH-adducts of substituted nitrobenzenes and phenylacetonitrile derivatives followed by reductive transformation of the nitro group with silylating or acylating agents leads to 9-cyanoacridines. The method was found to be superior to the earlier one-pot approach, resulting in better yields and a broader scope of the reaction.
REACTION OF 4-CHLORO-1-NITROBENZENE WITH o-SUBSTITUTED PHENYLACETONITRILES; SYNTHESIS OF 8-CHLORO-1-METHYL(AND METHYLTHIOMETHYL)-6-(2-SUBSTITUTED PHENYL)-4H-s-TRIAZOLO-1,4-BENZODIAZEPINES
Vejdelek, Zdenek,Holubek, Jiri,Ryska, Miroslav,Koruna, Ivan,Svatek, Emil,et.al.
, p. 2545 - 2563 (2007/10/02)
Reactions of 4-chloro-1-nitrobenzene with 2-methyl-, 2-methoxy- and 2-(methylthio)phenylacetonitrile in methanolic potassium hydroxide gave mixture from which the excepted 3-aryl-5-chloro-2,1-benzisoxazoles Ia-c were isolated in addition to the 2H-indoles IIIa and IIIc and acridines VIII and IX.The 2,1-benzisoxazoles were reduced to the 2-aminobenzophenones XIIa-c which were transformed via the phthalimidoacetamido compounds XIIIa-c to 5-aryl-7-chloro-1,3-dihydro-1,4-benzodiazepine-2-ones XVa-c.Treatment with phosphorus pentasulfide led to the thiones XVIa-c which reacted in boiling butanol either with acetohydrazide or with (methylthio)acetohydrazide to give the title compounds XVIIa-c and XVIIIa-c.They showed only weak anticonvulsant, incoordinating and central depressant effects.
