69111-49-5Relevant academic research and scientific papers
Synthesis of indolines via a SmI2 promoted domino nitro reduction-intramolecular aza-Michael reaction
Ramos, Josierika A. Ferreira,Araújo, Carolina S.,Nagem, Tanus J.,Taylor, Jason G.
, p. 54 - 58 (2015/01/30)
A simple and straightforward synthesis of substituted indolines based on a domino nitro reduction intramolecular aza-Michael reaction is described. The reaction employs Samarium diiodide under mild conditions for the addition of dibromoacetic acid to substituted 2-(2-nitrophenyl) acetaldehyde derivatives and their subsequent cyclization upon nitro group reduction to provide corresponding indoline heterocycles in good yields. This "one pot" strategy also permitted the expeditious synthesis of a 1,2,3,4-tetrahydroquinoline, whereas the seven-membered 2,3,4,5-tetrahydrobenzoazepines compounds were not formed under these reaction conditions.
Facile synthesis of indolines by a tandem nitro-reduction Aza Michael addition reaction
Ventura, Wellington Martins,Souza De Assis, Luiz Guilherme,Taylor, Jason Guy
, p. 2023 - 2029 (2013/10/22)
A diverse array of substrates are conveniently prepared by coupling diazonium salts to ethyl vinyl ether and subjecting the resultant aldehyde intermediate to a Wittig reaction to provide α,β-unsaturated esters with only one purification step. The cyclisation of 4-aryl-but-2-enoates is carried out in the presence of stoichiometric amounts of SnCl 22H2O and thus this one-pot strategy also permitted the expeditious synthesis of indolines in good yield. The Japan Institute of Heterocyclic Chemistry.
Facile, environmentally friendly synthesis of benzaldehyde and phenylacetaldehyde analogs from readily available toluene derivatives
Dai, Liyan,Yu, Jie,Chen, Yingqi,Yu, Shichao
, p. 3078 - 3084 (2011/09/14)
A facile environmentally friendly synthesis of bezaldehyde and phenylacetaldehyde analogs from readily available toluene derivatives is described. Oxidation of the styrylamines by H2O2 H2O2 affords benzaldehydes in moderate yields, while the hydrolysis of styrylamines afforded phenylacetaldehyde analogs in good yields. Copyright
Synthesis of Substituted Indoles via Meerwein Arylation
Raucher, Stanley,Koolpe, Gary A.
, p. 2066 - 2069 (2007/10/02)
A new method for the synthesis of substituted indoles is detailed.Meerwein arylation of 4- and 6-substituted 2-nitrobenzenediazonium chlorides with vinyl acetate or vinyl bromide and subsequent reductive cyclization of the resulting adducts affords the corresponding 6- and 4-substituted (CH3, OCH3, Cl, Br, CF3) indoles.The diazonium bisulfates of weakly basic 2-nitroanilines (4-Cl, 6-Br, 4-CF3) gave higher yields of Meerwein arylation adducts than the corresponding diazonium chlorides.Coupling of 2-nitrobenzenediazonium chloride with 2-acetoxy-1-alkenes followed byreductive cyclization affords 2-alkylindoles.
