1309371-20-7Relevant articles and documents
Visible-light driven synthesis of polycyclic benzo[: D] [1,3]oxazocine from 2-aminochalcone
Chen, Junhan,Gao, Yu-Qi,He, Yu-Peng,Hou, Yi,Li, Ruoxin,Xie, Weiqing,Zhang, Sheng-Yong,Zhu, Liming
supporting information, p. 6739 - 6742 (2020/07/13)
Herein, we report a tandem cycloisomerization/nucleophilic addition/cyclization of 2-amino chalcone with bifunctional nucleophiles driven by visible light. This cascade process is realized by the irradiation of a blue LED at room temperature, which provides a concise route to structurally diverse benzo[d][1,3]oxazocine scaffolds. Mechanistic studies show that the reaction is initiated with the E to Z isomerization of a C-C double bond upon the irradiation of visible light, followed by cyclization/rearomatization to generate a transient quinolinium intermediate, which is trapped by the nucleophile and cyclized to produce the polycyclic benzo[d][1,3]oxazocine.
Organocatalytic enantioselective cascade aza-michael/michael addition for the synthesis of highly functionalized tetrahydroquinolines and tetrahydrochromanoquinolines
Yang, Wen,He, Hai-Xiao,Gao, Yu,Du, Da-Ming
supporting information, p. 3670 - 3678 (2014/01/06)
An efficient organocatalytic highly asymmetric cascade aza-Michael/Michael addition reaction for the synthesis of tetrahydroquinolines and tetrahydrochromanoquinolines has been developed. This cascade reaction proceeds well at low catalyst loading with a broad substrate scope, furnishing the desired products in excellent yields with excellent diastereoselectivities and enantioselectivities (up to >99:1 dr, 99% ee) under mild conditions. Importantly, it is the first catalytic asymmetric method for tetrahydrochromanoquinolines. This protocol provides a straightforward entry to highly functionalized chiral tetrahydroquinoline and tetrahydrochromanoquinoline derivatives from simple starting materials. Copyright
Hydrogenation of ortho-nitrochalcones over Pd/C as a simple access to 2-substituted 1, 2, 3, 4-tetrahydroquinolines
Patti, Angela,Pedotti, Sonia
experimental part, p. 5607 - 5611 (2010/09/18)
The preparation of some 2-substituted-1, 2, 3, 4-tetrahydroquinoline has been achieved by the one-pot reductive intramolecular cyclization of ortho-nitrochalcones with gaseous hydrogen in the presence of a Pd/C catalyst and the best selectivity was observed using CH2Cl2 as solvent. The method is operationally simple and versatile since ortho-nitrocalchones are easily accessible by Claisen-Schmidt condensation of 2-nitrobenzaldehydes and enolizable ketones. Selected examples on structurally different substrates have been considered and a novel tetrahydroquinoline and a benzo[h]tetrahydroquinoline were prepared and characterised.