5883-82-9Relevant articles and documents
Synthesis of Indoles and Pyrroles Utilizing Iridium Carbenes Generated from Sulfoxonium Ylides
Vaitla, Janakiram,Bayer, Annette,Hopmann, Kathrin H.
, p. 4277 - 4281 (2017/04/03)
Metal carbenes can undergo a myriad of synthetic transformations. Sulfur ylides are potential safe precursors of metal carbenes. Herein, we report cascade reactions that involve carbenoids derived from sulfoxonium ylides for the efficient and regioselective synthesis of indoles and pyrroles. The tandem action of iridium and Br?nsted acid catalysts enables rapid assembly of the heterocycles from unmodified anilines or readily accessible enamines under microwave irradiation. The key mechanistic steps are the catalytic transformation of the sulfoxonium ylide into an iridium–carbene complex, followed by N?H or C?H functionalization of an aniline or enamine, respectively, and a final acid-catalyzed cyclization. The present method was successfully applied to the synthesis of the densely functionalized pyrrole subunit of atorvastatin.
A selective reductive amination of aldehydes by the use of Hantzsch dihydropyridines as reductant
Itoh, Takashi,Nagata, Kazuhiro,Miyazaki, Michiko,Ishikawa, Hiroyuki,Kurihara, Ayako,Ohsawa, Akio
, p. 6649 - 6655 (2007/10/03)
Direct reductive amination of an aldehyde was carried out using a Hantzsch dihydropyridine as the reductant in the presence of a catalytic amount of scandium triflate. The reaction was highly selective towards aldehydes over ketones, and other reducible functional groups did not affect the reaction.
Reaction of Symmetric N1 ,N2-Diarylamidines with α-Bromoacetophenone and Ethyl 2-Bromoethanoate
Gomaa, Mohsen Abdel-Motaal
, p. 654 - 655 (2007/10/03)
2-Bromo-1-{aryl[1-(arylimino)ethyl]amino}-1-phenylethanol derivatives 3a, 3b were obtained from the reaction of N1 ,N2-diarylacetamidines 1a, 1b with α-bromoacetophenone 2, while 1a, 1b with ethyl 2-bromoethanoate 4 afforded 2-{[1-(arylimino)]ethyl}aminoethanoic acid derivatives 5a, 5b; N1,N2-diarylformamidines 6a, 6b reacted with 2 and 4 to give the arylaminoacetophenones 8a, 8b and N-arylglycine ethyl esters 11a, 11b respectively together with the corresponding formanilides 9a, 9b.