1021684-82-1Relevant articles and documents
One pot synthesis of pyrrolo[3,4-c]quinolinone/pyrrolo[3,4-c]quinoline derivatives from 2-aminoarylacrylates/2-aminochalcones and tosylmethyl isocyanide (TosMIC)
Lu, Xin-Mou,Li, Jian,Cai, Zhong-Jian,Wang, Rong,Wang, Shun-Yi,Ji, Shun-Jun
, p. 9471 - 9477 (2014)
An efficient and practical synthetic approach to access to 2H-pyrrolo[3,4-c]quinolin-4(5H)-one/2H-pyrrolo[3,4-c]quinoline derivatives by the reaction of 2-aminoarylacrylates/2-aminochalcones and tosylmethyl isocyanide (TosMIC) via a one pot van Leusen rea
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
, p. 3670 - 3678 (2013)
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
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.
On-Water Synthesis of 2-Substituted Quinolines from 2-Aminochalcones Using Benzylamine as the Nucleophilic Catalyst
Lee, So Young,Cheon, Cheol-Hong
, p. 13036 - 13044 (2018/11/20)
On-water synthesis of 2-substituted quinolines from 2-aminochalcone derivatives was developed using benzylamine as the nucleophilic catalyst. Various 2-aminochalcones could be applied to this protocol, and the desired 2-substituted quinoline products were isolated in excellent yields by simple filtration. Furthermore, we elucidated the role of benzylamine in this transformation and provided the detailed reaction mechanism. This protocol has several additional advantages, such as simple operation, broad substrate scope, good functional group tolerance, easy product isolation, recycling of the catalyst, and gram-scale synthesis.