3749-11-9Relevant academic research and scientific papers
A Cascade of acid-promoted c-o bond cleavage and redox reactions: From oxa-bridged benzazepines to benzazepinones
Zhang, Yuewei,Yang, Fengzhi,Zheng, Lianyou,Dang, Qun,Bai, Xu
, p. 6041 - 6043 (2015/01/09)
A sequence of C-O bond cleavage and redox reactions in oxa-bridged azepines was realized under acid promoted conditions. This protocol provides an atom-economical and straightforward approach to access benzo[b]azepin-5(2H)-ones in high yields. The formal synthesis of tolvaptan was achieved by exploiting this new transformation.
Intramolecular Pd(0)-catalyzed reactions of (2-iodoanilino)-aldehydes: A joint experimental-computational study
Sole, Daniel,Mariani, Francesco,Fernandez, Israel,Sierra, Miguel A.
, p. 10272 - 10284 (2013/01/15)
An extensive joint experimental-computational density functional theory (DFT) study has been carried out to gain insight into the factors that control the chemoselectivity (i.e., acylation vs α-arylation reaction) of palladium-catalyzed cyclizations of (2-iodoanilino)-aldehydes. To this end, the nature of the tethers joining the aniline nitrogen and the aldehyde moiety, different palladium precatalysts and reaction conditions (base and temperature), as well as different additives (mono- and bidendate ligands) has been explored. The adequate selection of these variables allows for the control of the selectivity of the process. Thus, (2-iodoanilino)-aldehydes generally lead to the formation of nucleophilic addition derived products when Cs 2CO3/Et3N is used as base. In contrast, the use of stronger bases like KtOBu (in the presence of PhOH) mainly forms α-arylation reaction products. The different reaction pathways leading to the experimentally observed reaction products have been studied by means of computational tools.
