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
tert-Butoxide-Mediated Synthesis of 3,4′-Biquinolines from 2-Aminochalcones
Jeon, Jiye,Lee, So Young,Cheon, Cheol-Hong
, p. 2360 - 2364 (2019)
A novel protocol to synthesize 3,4’-biquinolines from 2-aminochalcones in the presence of a stoichiometric amount of sodium tert-butoxide as the nucleophilic promotor was developed. Conjugate addition of tert-butoxide to 2-aminochalcones provided the corresponding enolates, which underwent Michael addition to another molecule of 2-aminochalcone to afford a dimeric species of 2-aminochalcones. Subsequent cyclization between the amino and carbonyl groups followed by aromatization provides 3,4’-biquinoline products. Various 2-aminochalcones were submitted to this protocol and the desired 3,4’-biquinoline products were obtained in good to high yields in a short reaction time. (Figure presented.).
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.
Continuous Flow Synthesis of Quinolines via a Scalable Tandem Photoisomerization-Cyclization Process
Di Filippo, Mara,Baumann, Marcus
, p. 6199 - 6211 (2020/08/26)
A continuous photochemical process is presented that renders a series of quinoline products via an alkene isomerization and cyclocondensation cascade. It is demonstrated that a high-power LED lamp generates the desired targets with higher productivity and efficiency than a medium-pressure Hg-lamp. The scope of this tandem process is established and allows for the generation of various substituted quinolines in high yields and with throughputs of greater than one gram per hour. Finally, this effective flow process is coupled with a telescoped hydrogenation reaction to render a series of tetrahydroquinolines including the antimalarial natural product galipinine.
Synthesis of 2-Substituted Quinolines from 2-Aminostyryl Ketones Using Iodide as a Catalyst
Lee, So Young,Jeon, Jiye,Cheon, Cheol-Hong
, p. 5177 - 5186 (2018/05/15)
A new protocol for the synthesis of 2-substituted quinolines from 2-aminostyryl ketones has been developed using iodide as a nucleophilic catalyst. Conjugate addition of iodide to 2-aminostyryl ketones yielded the corresponding β-iodoketones, which could have a conformation where the amino and carbonyl groups are proximal through free rotation about the Cα-Cβ single bond. Subsequent condensation between the amino and carbonyl groups followed by elimination of hydrogen iodide provided the corresponding quinolines, with regeneration of the iodide catalyst.
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.
Blue-light-promoted carbon-carbon double bond isomerization and its application in the syntheses of quinolines
Chen, Xinzheng,Qiu, Shuxian,Wang, Sasa,Wang, Huifei,Zhai, Hongbin
supporting information, p. 6349 - 6352 (2017/08/10)
A blue-light-promoted carbon-carbon double bond isomerization in the absence of any photoredox catalyst is reported. It provides rapid access to a series of quinolines in good to excellent yields under simple aerobic conditions. The protocol is direct, catalyst-free and operationally convenient.
Cross-Cycloaddition of Two Different Isocyanides: Chemoselective Heterodimerization and [3+2]-Cyclization of 1,4-Diazabutatriene
Hu, Zhongyan,Yuan, Haiyan,Men, Yang,Liu, Qun,Zhang, Jingping,Xu, Xianxiu
supporting information, p. 7077 - 7080 (2016/07/06)
A new cross-cycloaddition reaction between a wide range of isocyanides and 2-isocyanochalcones (or analogues) was developed for the expeditious synthesis of pyrrolo[3,4-b]indoles under thermal conditions. On the basis of the experimental results and DFT c
A new and direct synthesis of chalcones via TFAA-H3PO 4 mediated c-c bond forming reaction
Kankanala, Kavitha,Reddy, Lingam Venkata,Reddy, Vangala Ranga,Mukkantia, Khagga,Pal, Sarbani
scheme or table, p. 53 - 59 (2012/04/18)
A number of α,β-unsaturated carboxylic acids were reacted with electron rich arenes or heteroarene in the presence of trifluoroacetic anhydride (TFAA) and H3PO4 at room temperature to give a variety of chalcone derivatives in good to
