1017572-70-1Relevant articles and documents
Synthesis of substituted pyridines and quinolines
Hill, Matthew D.,Movassaghi, Mohammad
, p. 1115 - 1119 (2007)
A variety of N-vinyl and N-aryl amides were converted to the corresponding pyridine and quinoline derivatives, respectively. Amide activation and nucleophilic addition of copper(I) (trimethylsilyl)acetylide efficiently provided the desired alkynyl imines. Ruthenium-catalyzed protodesilylation and cycloisomerization of these imines gave the corresponding azaheterocycles. Georg Thieme Verlag Stuttgart.
Domino 1,4- And 1,6-Addition Reactions of Ketene Silyl Acetals to Dialkynyl Imines Promoted by Aluminum Chloride: Synthesis of Multifunctionalized β-Lactams
Hachiya, Iwao,Nakamura, Kenta,Hara, Masaya,Sato, Koki,Shimizu, Makoto
, p. 14770 - 14794 (2019/11/13)
Domino 1,4- and 1,6-addition reactions of ketene silyl acetals to dialkynyl imines are disclosed. Aluminum chloride promoted domino 1,4- and 1,6-addition reactions of ketene silyl acetals to dialkynyl imines to give a variety of alkenyl iminocyclobutenones in moderate to good yields. The chemoselective reduction of alkenyl iminocyclobutenones and the subsequent thermal rearrangement of resulting alkenyl aminocyclobutenones in the presence of appropriate amines provided cis or trans multifunctionalized β-lactams in moderate to high yields with good to high diastereoselectivities.
Metal-free synthesis of alkynyl imines using an oxophosphonium-mediated approach at ambient temperatures
Dong, Qing-Li,Liu, Guan-Sai,Zhou, Hai-Bin,Chen, Lin,Yao, Zhu-Jun
, p. 1636 - 1640 (2008/09/18)
A metal-free approach was developed for the mild synthesis of N-aryl α-alkynyl imines from corresponding amide precursors for the first time. The electronic effects of substrates and the reaction mechanisms were investigated and discussed. This newly deve
Synthesis of substituted pyridine derivatives via the ruthenium-catalyzed cycloisomerization of 3-azadienynes
Movassaghi, Mohammad,Hill, Matthew D.
, p. 4592 - 4593 (2007/10/03)
We describe a two-step conversion of various N-vinyl and N-aryl amides to the corresponding substituted pyridines and quinolines, respectively. The process involves the direct conversion of amides, including sensitive N-vinyl amides, to the corresponding trimethylsilyl alkynyl imines followed by a ruthenium-catalyzed protodesilylation and cycloisomerization. A wide range of new alkynyl imines are prepared and readily converted to the corresponding azaheterocycles. Copyright
