77340-84-2Relevant articles and documents
Synthesis of Indoles by Reductive Cyclization of Nitro Compounds Using Formate Esters as CO Surrogates
Ahmed Fouad, Manar,Ferretti, Francesco,Formenti, Dario,Milani, Fabio,Ragaini, Fabio
supporting information, p. 4876 - 4894 (2021/09/20)
Alkyl and aryl formate esters were evaluated as CO sources in the Pd- and Pd/Ru-catalyzed reductive cyclization of 2-nitrostyrenes to give indoles. Whereas the use of alkyl formates requires the presence of a ruthenium catalyst such as Ru3(CO)12, the reaction with phenyl formate can be performed by using a Pd/phenanthroline complex alone. Phenyl formate was found to be the most effective CO source and the desired products were obtained in excellent yields, often higher than those previously reported using pressurized CO. The reaction tolerates many functional groups, including sensitive ones like a free aldehydic group or a pendant pyrrole. Detailed experiments and kinetic studies allow to conclude that the activation of phenyl formate is base-catalyzed and that the metal doesn't play a role in the decarbonylation step. The reactions can be performed in a single thick-walled glass tube with as little as 0.2 mol-% palladium catalyst and even on a 2 g scale. The same protocol can be extended to other nitro compounds, affording different heterocycles.
Lewis-acid-catalyzed benzylic reactions of 2-methylazaarenes with aldehydes
Mao, Dan,Hong, Gang,Wu, Shengying,Liu, Xin,Yu, Jianjun,Wang, Limin
, p. 3009 - 3019 (2014/05/20)
Lewis-acid-catalyzed benzylic reactions of 2-methylazaarenes with aldehydes have been investigated. Series of azaarene derivatives were afforded by this reaction. 2-(Pyridin-2-yl)ethanols with common substituents were formed through the LiNTf2-promoted aldol reaction for the first time. 2-Alkenylpyridines, exclusively in the form of the E isomers, were synthesized in the presence of LiNTf2 cooperated with H2NTf. In the presence of La(Pfb)3 as catalysis, 2-alkenylquinolines were obtained in high yields through the reactions between 2-methylquinolines and aldehydes under air.
Kinetic Energy Release and Hammond Postulate During Intramolecular Aromatic Substitution in 2-Stilbazole Ions
Schubert, Ralf,Ramana, Devalla Venkata,Gruetzmacher, Hans-Friedrich
, p. 3758 - 3774 (2007/10/02)
In the mass spectra of 2-stilbazoles 1a - 1g and 3- and 4-stilbazoles (2 resp. 3), C13H10N+ ions, m/z = 180, are formed with high intensities by loss of a H-atom or of a substituent.This is the only fragmentation reaction available to metastable molecular
