38055-79-7Relevant academic research and scientific papers
An indenone synthesis involving a new aminotransfer reaction and its application to dibenzopentalene synthesis
Katsumoto, Kenta,Kitamura, Chitoshi,Kawase, Takeshi
, p. 4885 - 4891 (2011/10/31)
o-(Phenylethynyl)phenyllithiums, generated by treatment of o-(phenylethynyl)bromobenzenes with tBuLi, were quenched with N,N-dimethylcarboamides to afford various 2-phenylindenone derivatives in moderate to good yields upon acidic workup. The choice of lithiation reagents was critical. When n-butyllithium was used the yields were reduced. The N-alkyl groups in the carboamides were also important: quenching with N,N-diethylbenzamides also afforded 2,3-diphenylindenones as the sole isolated products, but quenching with N-benzoylpiperidine led to 2-benzoyltolane in good yield. Control experiments revealed that the reactions proceed through a multi-step reaction sequence involving a novel intramolecular transamination to the α-acetylenic carbon of the alkynyl group. The method was applicable to the synthesis of dibenzopentalene derivatives as well as various indenone derivatives. A mechanism for the reaction is discussed.
α,β-UNSATURATED THIO COMPOUNDS. XX. -CYCLOADDITION OF 3-AMINO-2-ARYL-1-INDENETHIONES TO NITRILIUM BETAINES AND PHENYL AZIDE
Korchevin, N. A.,Usov, V. A.,Voronkov, M. G.,Borodina, N. M.
, p. 1150 - 1154 (2007/10/02)
N,N-Disubstituted 3-amino-2-aryl-1-indenethiones react with the N-oxides of aromatic nitriles or with benzonitrile phenylimine to form 5-spiroindene-substituted 1,4,2-oxathiazoles and 2-spiroindene-substituted 1,3,4-thiadiazolines.With phenyl azide only the transformation of the thiocarbonyl group into a phenylimine group occurs.In the reaction of N-unsubstituted aminoindenethione with benzonitrile N-oxide N,N-diacylation and the parallel transformation of the thione function into ketone function are observed.The reaction of 3-phenylamino-1-indenethione in the iminoenethiol form with benzonitrile N-oxide leads to the product from S-acylation and cycloaddition at the C=N bond with the formation of a 1,4,2-oxadiazoline ring.
α,β-UNSATURATED THIO COMPOUNDS. XII. SYNTHESIS AND PROPERTIES OF S-ALKYL DERIVATIVES OF 3-AMINOINDENE-1-THIONES
Korchevin, N. A.,Usov, V. A.,Oparina, L. A.,Dorofeev, I. A.,Tsetlin, Ya. S.,Voronkov, M. G.
, p. 1561 - 1566 (2007/10/02)
2-Substituted 3-amino-1-indenethiones are alkylated by alkyl iodides and triethyloxonium tetrafluoroborate with the formation of the corresponding salts of the S-alkyl derivatives or their bases.Hydrothiolysis, hydrolysis, and methanolysis of the N,N-disubstituted 3-alkylthio-2-arylindene-1-immonium salts lead to the production of new or little known types of organosulfur compounds.
