933217-40-4Relevant academic research and scientific papers
Palladium-catalyzed aerobic oxidative coupling of allylic alcohols with anilines in the synthesis of nitrogen heterocycles
Kumar, Gangam Srikanth,Singh, Diksha,Kumar, Manish,Kapur, Manmohan
, p. 3941 - 3951 (2018/04/14)
We report herein an unprecedented and expedient Pd-catalyzed oxidative coupling of allyl alcohols with anilines to afford β-amino ketones which are converted into substituted quinolines in a one-pot fashion. The exclusive preference for N-alkylation over N-allylation makes this approach unique when compared to those reported in literature. Detailed mechanistic investigations reveal that the conjugate addition pathway was the predominant one over the allylic amination pathway. The notable aspects of the present approach are the use of readily available, bench-stable allyl alcohols and molecular oxygen as the terminal oxidant, in the process dispensing the need for unstable and costly enones. Further, we explored the synthetic utility of β-amino ketones through an intramolecular α-arylation methodology and a one-pot domino annulation, thereby providing rapid access to indolines and quinolines.
Conversion of 3-benzoyl-1-methyl-4-phenyl-γ-piperidol by arylamines and arylhydrazines. Synthesis of 3-arylamino-1-oxo-1-phenylpropanes and 1,3-diarylpyrazoles and their fragmentation under electron impact
Volkov,Kutyakov,Levov,Polyakova,An, Le Tuan,Soldatova,Terentiev,Soldatenkov
, p. 1260 - 1268 (2008/09/19)
It has been established that on heating, 3-benzoyl-4-hydroxy-1-methyl-4- phenylpiperidine is ring-opened in the presence of arylamines by a type of retroaldol reaction, with subsequent transamination of the intermediate Mannich base and the formation of 3-arylamino-1-oxo-1-phenylpropanes. When using arylhydrazines this γ-piperidol is recyclized with the formation of 1,3-diarylpyrazoles and their 4,5-dihydro derivatives. The mass spectral behavior of a series of 3-arylamino-substituted 1-phenylpropanones has been studied.
Reaction of 3-benzoyl-1-methyl-4-phenyl-γ-piperidol with arylamines and arylhydrazines. Synthesis of 3-arylamino-1-oxo-1-phenylpropanes and 1,3 diarylpyrazoles and their fragmentation under electron impact
Volkov,Kutyakov,Levov,Polyakova,Anh, Le Tuan,Soldatova,Terentiev,Soldatenkov
, p. 445 - 453 (2008/12/20)
Upon heating in the presence of arylamines 3-benzoyl-4-hydroxy-1-methyl-4- phenylpiperidine decyclizes via a retroaldol type reaction with subsequent transamination of the intermediate Mannich base to give 3-arylamino-1-oxo-1- phenylpropanes. In the case of the use of arylhydrazines this γ-piperidol recyclizes to give 1,3-diarylpyrazoles and their 4,5-dihydro derivatives. The mass spectroscopic behavior of a series of 3-arylamino-substituted 1-phenylpropanones has been studied.
