104803-80-7Relevant articles and documents
Rhodium(II)-catalyzed intramolecular annulation of 1-sulfonyl-1,2,3- triazoles with pyrrole and indole rings: Facile synthesis of N-bridgehead azepine skeletons
Yang, Jin-Ming,Zhu, Cheng-Zhi,Tang, Xiang-Ying,Shi, Min
supporting information, p. 5142 - 5146 (2014/05/20)
A convenient and efficient synthetic method has been developed to construct highly functionalized N-bridgehead azepine skeletons, which are of great importance in biological and pharmaceutical industry. The reaction proceeds through a rhodium(II) azavinyl carbene intermediate, which initiated the intramolecular C-H functionalization with pyrrolyl and indolyl rings. A variety of azepine derivatives were obtained in moderate to good yields under mild reaction conditions with high chemoselectivity. Several interesting derivatizations of the resulting products demonstrate that this method is synthetically valuable and useful. Heads up: A convenient and efficient synthetic method of highly functionalized N-bridgehead azepine skeletons was developed using a rhodium(II)-catalyzed intramolecular annulation of pyrrolyl and indolyl triazoles. Several interesting transformations of the products into poly-heterocyclic products and the reaction mechanism are disclosed. Ts=4-toluenesulfonyl.
Photosensitized oxidations of substituted pyrroles: Unanticipated radical-derived oxygenated products
Alberti, Mariza N.,Vougioukalakis, Georgios C.,Orfanopoulos, Michael
supporting information; experimental part, p. 7274 - 7282 (2010/01/16)
(Chemical Equation Presented) Photooxidation of pyrrole adducts 7-10 has been investigated in order to establish a general reaction pattern andmechanism for the formation of the resulting oxygenated products. The reactions were performed in several solvents utilizing both type I and type II sensitizers. In most cases, photooxidations gave complex mixture of products. Among these products, 5,5- or 6,5-bicyclic lactams (11, 15, and 19), maleimide 12 unsaturated γ-lactams (16 and 20), 5-hydroxylactams (13, 17, and21), and 5-methoxylactams (14, 18, and22) wereisolated and characterized. Photooxidation of 2,5-dimethyl-substituted pyrrole 10 in aprotic solvents unexpectedly afforded aldehyde 23 as the major product. Moreover, photooxidation of pyrrole adduct 10 in protic solvents exclusively gave the unprecedented solvent-trapped products 24-27. The formation of products 11-22 was rationalized by the intermediacy of a commonendoperoxide intermediate, whichcould be formedby both type I and type II mechanisms. Compounds 23-27 were most probably formed via an electron-transfer mechanism. 2009 American Chemical Society.