1264932-08-2Relevant academic research and scientific papers
TBAI/TBHP-catalyzed [3 + 2]cycloaddition/oxidation/aromatization cascade and online ESI-MS mechanistic studies: Synthesis of pyrrolo[2,1-a]isoquinolines and indolizino[8,7-b]indoles
Nekkanti, Shalini,Kumar, Niggula Praveen,Sharma, Pankaj,Kamal, Ahmed,Nachtigall, Fabiane M.,Forero-Doria, Oscar,Santos, Leonardo S.,Shankaraiah, Nagula
, p. 2671 - 2677 (2016)
A facile [3 + 2]cycloaddition/oxidation/aromatization cascade reaction for the synthesis of pyrrolo[2,1-a]isoquinolines and indolizino[8,7-b]indoles has been developed. This tandem approach was accomplished by employing tert-butyl hydroperoxide (TBHP) as
Chlorophyll-catalyzed tandem oxidation /[3+2] cycloaddition reactions toward the construction of pyrrolo[2,1-a]isoquinolines under visible light
Hosseini-Sarvari, Mona,Koohgard, Mehdi
, (2021)
Chlorophyll as a green, cheap, and affordable natural pigment was used in the one-pot synthesis of pyrrolo[2,1-a]isoquinoline scaffold under visible light. This photocatalytic approach has handled oxidation/[3 + 2] cycloaddition/aromatization cascade reac
Building a Pyrazole–Benzothiadiazole–Pyrazole Photosensitizer into Metal–Organic Frameworks for Photocatalytic Aerobic Oxidation
Jin, Ji-Kang,Wu, Kun,Liu, Xin-Yi,Huang, Guo-Quan,Huang, Yong-Liang,Luo, Dong,Xie, Mo,Zhao, Yifang,Lu, Weigang,Zhou, Xiao-Ping,He, Jian,Li, Dan
supporting information, p. 21340 - 21349 (2021/12/17)
Charge separation plays a crucial role in regulating photochemical properties and therefore warrants consideration in designing photocatalysts. Metal–organic frameworks (MOFs) are emerging as promising candidates for heterogeneous photocatalysis due to their structural designability and tunability of photon absorption. Herein, we report the design of a pyrazole–benzothiadiazole–pyrazole organic molecule bearing a donor–acceptor–donor conjugated π-system for fast charge separation. Further attempts to integrate such a photosensitizer into MOFs afford a more effective heterogeneous photocatalyst (JNU-204). Under visible-light irradiation, three aerobic oxidation reactions involving different oxygenation pathways were achieved on JNU-204. Recycling experiments were conducted to demonstrate the stability and reusability of JNU-204 as a robust heterogeneous photocatalyst. Furthermore, we illustrate its applications in the facile synthesis of pyrrolo[2,1-a]isoquinoline-containing heterocycles, core skeletons of a family of marine natural products. JNU-204 is an exemplary MOF platform with good photon absorption, suitable band gap, fast charge separation, and extraordinary chemical stability for proceeding with aerobic oxidation reactions under visible-light irradiation.
Dual organic dyes as a pseudo-redox mediation system to promotion of tandem oxidation /[3+2] cycloaddition reactions under visible light
Koohgard, Mehdi,Hosseinpour, Zeinab,Hosseini-Sarvari, Mona
, (2021/05/10)
An atom- and step-economy protocol has been developed to synthesize some new biologically active pyrrolo[2,1-a]isoquinoline alkaloids via redox mediation system under visible light irradiation. A vast variety of double and triple bonds, as dipolarophiles, treated with in situ generated azomethine ylides to prepare corresponding products in good to excellent yields. This metal-free method effectively promoted oxidation/[3 + 2] cycloaddition/oxidative/aromatization domino reaction without further oxidant using dual organic dyes as pseudo-redox mediation system. Besides, for most of the products, product precipitate was readily separated from reaction media. To the best of our knowledge, this is the first report of dual dyes as a pseudo-redox mediation system.
CuBr/NHPI co-catalyzed aerobic oxidative [3 + 2] cycloaddition-aromatization to access 5,6-dihydro-pyrrolo[2,1-: A] isoquinolines
Xie, Zhiyu,Li, Fei,Niu, Liangfeng,Li, Hongbing,Zheng, Jincai,Han, Ruijing,Ju, Zhiyu,Li, Shanshan,Li, Dandan
, p. 6889 - 6898 (2020/10/02)
An efficient and enviromentally friendly CuBr/NHPI co-catalyzed aerobic oxidative [3 + 2] cycloaddition-aromatization cascade was realized with N-substituted tetrahydroisoquinolines and electron-deficient olefins. Under the mild conditions, the reaction p
Solvent-free and room temperature visible light-induced C-H activation: CdS as a highly efficient photo-induced reusable nano-catalyst for the C-H functionalization cyclization of: T -amines and C-C double and triple bonds
Firoozi, Somayeh,Hosseini-Sarvari, Mona,Koohgard, Mehdi
, p. 5540 - 5549 (2019/01/03)
Nano-sized CdS was successfully prepared, fully characterized and applied as a highly efficient reusable photocatalyst for the synthesis of pyrrolo[3,4-c]quinolone and pyrrolo[2,1-a]isoquinoline-8-carboxylate derivatives through a condensation reaction of N,N-dimethylanilines or alkyl 2-(3,4-dihydroisoquinolin-2(1H)-yl)acetates with maleimides via a C-H activation approach under benign and eco-friendly conditions at room temperature without using any solvent and oxidant under visible light irradiation. Besides, the prepared photocatalyst has been successfully applied for the condensation reaction of N,N-dimethylanilines with alkyl but-2-ynedioates or phenyl acetylenes for the synthesis of novel 1,2-dihydroquinoline-3,4-dicarboxylate and aryl-1,2-dihydroquinoline derivatives for the first time. Using this method, all favourable products were obtained in good yields and relatively short reaction times under benign conditions with the application of visible light irradiation, a renewable energy source. The catalyst was easily recovered and reused several times without any loss of its activity.
Pyrrole [2,1-a] isoquinoline alkaloid and preparation method and application thereof
-
Paragraph 0055; 0056; 0057, (2018/03/24)
The invention discloses pyrrole [2,1-a] isoquinoline alkaloid and a preparation method and medical application thereof, and belongs to the field of medicinal chemistry. The structural general formula of the pyrrole [2,1-a] isoquinoline alkaloid is as show
A diiodo-BODIPY postmodified metal-organic framework for efficient heterogeneous organo-photocatalysis
Quan, Ying,Li, Qiu-Yan,Zhang, Quan,Zhang, Wen-Qiang,Lu, Han,Yu, Jun-Hao,Chen, Jian,Zhao, Xinsheng,Wang, Xiao-Jun
, p. 23995 - 23999 (2016/03/15)
The organic photosensitizer diiodo-BODIPY has been covalently conjugated into a Zr(iv)-based metal-organic framework with UiO topology via postsynthetic modification, which serves as a highly active and recyclable heterogeneous photocatalyst for aerobic c
Sequential Photo-oxidative [3 + 2] Cycloaddition/Oxidative Aromatization Reactions for the Synthesis of Pyrrolo[2,1-a]isoquinolines Using Molecular Oxygen as the Terminal Oxidant
Fujiya, Akitoshi,Tanaka, Masanori,Yamaguchi, Eiji,Tada, Norihiro,Itoh, Akichika
, p. 7262 - 7270 (2016/08/30)
We report an efficient method for the synthesis of pyrrolo[2,1-a]isoquinoline derivatives using sequential [3 + 2] cycloaddition/oxidative aromatization reactions catalyzed by methylene blue with fluorescent light irradiation under an oxygen atmosphere. T
A general, simple and green process to access pyrrolo[2,1-a]isoquinolines using a KI/TBHP catalytic system
Huang, Huan-Ming,Huang, Fang,Li, Yu-Jin,Jia, Jian-Hong,Ye, Qing,Han, Liang,Gao, Jian-Rong
, p. 27250 - 27258 (2014/07/21)
A novel KI/TBHP-catalyzed 1,3-dipolar cycloaddition/oxidation/aromatization cascade reaction provided general, efficient and green access to biologically important pyrrolo[2,1-a]isoquinolines. The product pyrrolo[2,1-a]isoquinolines were obtained from rea
