69907-27-3Relevant academic research and scientific papers
A solvent-free manganese(II) -catalyzed Clauson-Kaas protocol for the synthesis of N-aryl pyrroles under microwave irradiation
Rohit, Kizhakkekuttu Radhakrishnan,Meera, Gopinadh,Anilkumar, Gopinathan
supporting information, p. 194 - 200 (2021/10/12)
The first manganese-catalyzed modified Clauson-Kaas reaction for N-substituted pyrrole synthesis using 2,5-dimethoxytetrahydrofuran with variously substituted aromatic amines has been developed (up to 89% yield). This interesting neat strategy is free from additives including co-catalysts, ligands, and acids. Relatively low cost, environmentally benign, and handy Mn(NO3)2·4H2O is employed as the catalyst under microwave conditions with a very short reaction time (20?min). The above qualities attest to the green nature of this reaction.
Synthesis of 1,3-Azaphospholes with Pyrrolo[1,2- a]quinoline Skeleton and Their Optical Applications
Wu, Di,Chen, Lingfeng,Ma, Shuangliang,Luo, Huiying,Cao, Jing,Chen, Runfeng,Duan, Zheng,Mathey, Francois
, p. 4103 - 4106 (2018/07/15)
A facile synthesis of 1,3-azaphospholes with a pyrrolo[1,2-a]quinoline skeleton has been described. These new annulated 1,3-azaphospholes exhibit good photoelectric performance and can be used as the emitting dopant in organic light-emitting diodes (OLEDs) and dye for bioimaging.
Synthesis of pyrrolo[1,2-a] quinolines and ullazines by visible light mediated one- and twofold annulation of N-arylpyrroles with arylalkynes
Das, Amrita,Ghosh, Indrajit,K?nig, Burkhard
supporting information, p. 8695 - 8698 (2016/07/15)
1-(2-Bromophenyl)-1H-pyrrole and 1-(2,6-dibromophenyl)-1H-pyrrole react in the presence of catalytic amounts of rhodamine 6G (Rh-6G) and N,N-diisopropylethylamine (DIPEA) under blue light irradiation with aromatic alkynes and subsequently cyclize intramol
A novel and convenient method for the preparation of 5-(diphenylmethylene)-1H-pyrrol-2(5H)-ones; synthesis and mechanistic study
Faigl, Ferenc,Deák, Szilvia,Mucsi, Zoltán,Hergert, Tamás,Balázs, László,Sándor, Boros,Balázs, Barbara,Holczbauer, Tamás,Nyerges, Miklós,Mátrav?lgyi, Béla
, p. 5444 - 5455 (2016/08/04)
An efficient, regioselective synthesis has been developed for the preparation of 5-(diphenylmethylene)-1H-pyrrol-2(5H)-ones from readily available 1H-pyrroles by sequential dibromination and selective organometallic bromine/lithium exchange followed by reaction with benzophenone. Comparison of various N-substituents was shown to demonstrate the high tolerance of the transformation to functional groups. The structures of the new products were determined by spectroscopic methods and confirmed by single-crystal X-ray diffraction measurement. In addition, theoretical study of the reaction mechanism and selective functionalization of the endocyclic double bond were also presented.
Steric vis-à-vis electronic influence of phosphines on biaryl motif: Ligand design for coupling reactions with Chloroarenes
Saha, Debajyoti,Ghosh, Raju,Dutta, Ranjan,Mandal, Achintya Kumar,Sarkar, Amitabha
, p. 89 - 97 (2015/01/09)
In order to assess relative contribution of steric factors and electron-richness of phosphine ligands on biaryl-type scaffolds, a set of 1-aryl-pyrazole/pyrrole derived ligands L1-L6 featuring either aryldicyclohexylphosphino or aryldiphenylphosphino donor group was synthesized. A bidentate coordination mode of ligands L1 or L2 was evident from a representative crystal structure that implied a possible hemilabile participation to facilitate catalytic steps. With N-arylpyrroles (L3-L5), where the second nitrogen donor on the heterocycle is absent, coupling reactions of unactivated chloroarenes still proceeded with comparable efficiency. Thus, suitably endowed triarylphosphines were found to be as efficient as more expensive aryldialkylphosphine analogs in reactions with chloroarenes, extending the scope of ligand design.
Steric vis-??-vis electronic influence of phosphines on biaryl motif: Ligand design for coupling reactions with Chloroarenes
Saha, Debajyoti,Ghosh, Raju,Dutta, Ranjan,Mandal, Achintya Kumar,Sarkar, Amitabha
, p. 89 - 97 (2015/03/05)
In order to assess relative contribution of steric factors and electron-richness of phosphine ligands on biaryl-type scaffolds, a set of 1-aryl-pyrazole/pyrrole derived ligands L1-L6 featuring either aryldicyclohexylphosphino or aryldiphenylphosphino donor group was synthesized. A bidentate coordination mode of ligands L1 or L2 was evident from a representative crystal structure that implied a possible hemilabile participation to facilitate catalytic steps. With N-arylpyrroles (L3-L5), where the second nitrogen donor on the heterocycle is absent, coupling reactions of unactivated chloroarenes still proceeded with comparable efficiency. Thus, suitably endowed triarylphosphines were found to be as efficient as more expensive aryldialkylphosphine analogs in reactions with chloroarenes, extending the scope of ligand design.
One-Pot Synthesis of Pyrrolo[1,2- a ]quinoxaline Derivatives via a Copper-Catalyzed Aerobic Oxidative Domino Reaction
Liu, Huanhuan,Duan, Tiantian,Zhang, Zeyuan,Xie, Caixia,Ma, Chen
supporting information, p. 2932 - 2935 (2015/06/30)
A copper-catalyzed process for the synthesis of pyrrolo[1,2-a]quinoxalines from readily available α-amino acids and 1-(2-halophenyl)-1H-pyrroles is described. Different functional groups were well tolerated to give the corresponding products.
L-(+)-Tartaric acid and choline chloride based deep eutectic solvent: An efficient and reusable medium for synthesis of N-substituted pyrroles via Clauson-Kaas reaction
Wang, Ping,Ma, Fei-Ping,Zhang, Zhan-Hui
, p. 259 - 262 (2014/11/07)
l-(+)-Tartaric acid-choline chloride based deep eutectic solvent has been found to be an effective promoted medium for Clauson-Kaas reaction of aromatic amines and 2,5-dimethoxytetrahydrofuran. Structurally diverse N-substituted pyrroles were obtained in high to excellent yields under mild conditions. The deep eutectic solvent is inexpensive, non-toxic, reusable and biodegradable.
2-(1-benzotriazolyl)pyridine: A robust bidentate ligand for the palladium-catalyzed C-C (Suzuki, Heck, Fujiwara-Moritani, Sonogashira), C-N and C-S coupling reactions
Verma, Akhilesh K.,Jha, Rajeev R.,Chaudhary, Ritu,Tiwari, Rakesh K.,Danodia, Abhinandan K.
, p. 421 - 438 (2013/05/08)
A new class of bidentate ligand, 1-(pyridine-2-yl)-1H-benzo[d][1,2,3] triazole has been designed and employed for the palladium-catalyzed C-C (Suzuki, Heck, Fujiwara-Moritani, and Sonogashira), C-N and C-S coupling reactions. The ligand was found to be inexpensive, thermally stable, easy to synthesize from easily accessible starting materials on a multigram scale, show simplicity in use, and robustness in application, making this ligand effective for different coupling reactions. Suitably, the donor ability of the N=N bond of the benzotriazole ring and lone pair of electrons on the N of the pyridine ring enhance the bidentate ability of the ligand.
A recyclable magnetic nanoparticles supported antimony catalyst for the synthesis of N-substituted pyrroles in water
Ma, Fei-Ping,Li, Pei-He,Li, Bao-Le,Mo, Li-Ping,Liu, Ning,Kang, Hui-Jun,Liu, Ya-Nan,Zhang, Zhan-Hui
, p. 34 - 41 (2013/06/26)
A new magnetic nanoparticle-supported antimony catalyst was prepared and evaluated as a recoverable catalyst for Clauson-Kaas reaction. The reaction proceeds efficiently in aqueous medium to give the corresponding N-substituted pyrroles in high yield. The immobilized catalyst could be easily recovered by magnetic separation and recycled for six times without significant loss of its catalytic activity.
