139437-20-0Relevant articles and documents
A ring expansion strategy towards diverse azaheterocycles
Li, Ruirui,Li, Bo,Zhang, Hongpeng,Ju, Cheng-Wei,Qin, Ying,Xue, Xiao-Song,Zhao, Dongbing
, p. 1006 - 1016 (2021)
The development of innovative strategies for the synthesis of N-heterocyclic compounds is an important topic in organic synthesis. Ring expansion methods to form large N-heterocycles often involve the cycloaddition of strained aza rings with π bonds. However, in some cases such strategies suffer from some limitations owing to the difficulties in controlling the regioselectivity and the accessibility of specific π-bond synthons. Here, we report the development of a general ring expansion strategy that involves a formal cross-dimerization between three-membered aza heterocycles and three- and four-membered-ring ketones through synergistic bimetallic catalysis. These formal cross-dimerizations of two different strained rings are efficient and scalable, and provide a straightforward and broadly applicable means of assembling diverse N-heterocycles, such as 3-benzazepinones, dihydropyridinones and uracils, which are versatile units in numerous drugs and biologically active compounds. Preliminary mechanistic studies revealed that the C–C bond of strained ring ketones is first cleaved by the Pd0 species during the reaction. [Figure not available: see fulltext.].
Synthesis of novel tetrahydrobenzazepinones
Busacca, Carl A.,Johnson, Robert E.
, p. 165 - 168 (2007/10/02)
The synthesis of novel tetrahydrobenzazepinones 1, 2, and 3 is described, as well as an improved synthesis of 4. The palladium catalyzed arylation approach to 1, 2, and 4 allows facile entry to benzazepinones lacking electron donating substituents on the
