827-60-1Relevant 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.
A facile synthesis of diaryl pyrroles led to the discovery of potent colchicine site antimitotic agents
Romagnoli, Romeo,Oliva, Paola,Salvador, Maria Kimatrai,Manfredini, Stefano,Padroni, Chiara,Brancale, Andrea,Ferla, Salvatore,Hamel, Ernest,Ronca, Roberto,Maccarinelli, Federica,Rruga, Fatlum,Mariotto, Elena,Viola, Giampietro,Bortolozzi, Roberta
, (2021/02/09)
Three different series of cis-restricted analogues of combretastatin A-4 (CA-4), corresponding to thirty-nine molecules that contained a pyrrole nucleus interposed between the two aryl rings, were prepared by a palladium-mediated coupling approach and evaluated for their antiproliferative activity against six human cancer cell lines. In the two series of 1,2-diaryl pyrrole derivatives, results suggested that the presence of the 3′,4′,5′-trimethoxyphenyl moiety at the N-1 position of the pyrrole ring was more favorable for antiproliferative activity. In the series of 3,4-diarylpyrrole analogues, three compounds (11i-k) exhibited maximal antiproliferative activity, showing excellent antiproliferative activity against the CA-4 resistant HT-29 cells. Inhibition of tubulin polymerization of selected 1,2 pyrrole derivatives (9a, 9c, 9o and 10a) was similar to that observed with CA-4, while the isomeric 3,4-pyrrole analogues 11i-k were generally from 1.5- to 2-fold more active than CA-4. Compounds 11j and 11k were the only compounds that showed activity as inhibitors of colchicine binding comparable to that CA-4. Compound 11j had biological properties consistent with its intracellular target being tubulin. This compound was able to block the cell cycle in metaphase and to induce significant apoptosis at a concentration of 25 nM, following the mitochondrial pathway, with low toxicity for normal cells. More importantly, compound 11j exerted activity in vivo superior to that of CA-4P, being able to significantly reduce tumor growth in a syngeneic murine tumor model even at the lower dose tested (5.0 mg/kg).
Rearrangement and cyclisation reactions on the 1-Arylpyrrol-2-iminyl-2-Aryliminopyrrol-1-yl radical energy surface
Borthwick, Scott,Foot, Jonathan,Ieva, Maria,McNab, Hamish,McNab, Lilian,Rozgowska, Emma J.,Wright, Andrew
supporting information, p. 161 - 175 (2021/02/02)
Independent generation of the iminyl (X = N) and pyrrol-1-yl (X = N) radicals by flash vacuum pyrolysis of the corresponding oxime ether and N-(dimethylamino) compound, respectively, provides two regioisomeric pyrrolo1,2-A]quinoxalines compounds. This shows that the radical species interconvert via the spirodienyl moeity at high temperatures. Corresponding generation of the pyrrol-1-yl (X = CH) radical gives the pyrrolo[1,2-A]quinoline as the only cyclised product. In this case, DFT calculations suggest that direct cyclisation of the pyrrol-1-yl takes place, rather than formation of the spirodienyl species and exclusive migration of the C-N bond.
Utilization of caffeine carbon supported cobalt catalyst in the tandem synthesis of pyrroles from nitroarenes and alkenyl diols
Balasubramaniam, Bhuvaneshwari,Dhara, Partha,Gupta, Raju K.,Kundu, Sabuj,Panja, Dibyajyoti,Sau, Anirban
, p. 244 - 254 (2021/09/07)
Employing bio-waste caffeine carbon-supported heterogeneous cobalt catalyst, synthesis of various substituted pyrrole derivatives is reported. In this methodology, pyrroles were synthesized through coupling between nitroarenes and alkenyl diols in a tandem manner. Among all the heterogeneous catalysts Co(OAc)2-CC-800 displayed the highest catalytic activity. Preparative scale synthesis of pyrroles and synthesis of anti-tubercular agent 5-(4-(1H-pyrrol-1-yl)phenyl)-1,3,4-oxadiazole-2-thiol revealed the practical applicability of this protocol. Several kinetic experiments and Hammett studies were conducted to understand the probable mechanism and electronic effects on this transformation.
Metal-Free Synthetic Shortcut to Octahydro-Dipyrroloquinoline Skeletons from 2,5-Cyclohexadienone Derivatives and l -Proline
Zhang, Can,Li, Jianbin,Wang, Xin,Shen, Xuan,Zhu, Dunru,Shen, Ruwei
, p. 10397 - 10406 (2021/07/31)
The tandem decarboxylative condensation-dimerization reaction of l-proline with 2,5-cyclohexadienones including p-quinone monoacetals, p-quinol ethers, and p-quinols is reported to provide a concise and rapid synthesis of octahydro-dipyrroloquinoline comp
Ligand and Cu freeN-arylation of indoles, pyrroles and benzylamines with aryl halides catalyzed by a Pd nanocatalyst
Paul, Abhijit,Chatterjee, Debnath,Banerjee, Srirupa,Yadav, Somnath
supporting information, p. 14447 - 14452 (2020/09/21)
Herein, theN-arylation of aromatic heterocycles like indoles and pyrroles is reported by a Pd nanocatalyst under ligand- and Cu-free conditions. The reaction conditions tolerate several functional groups and work very efficiently for aryl iodides and bromides. Aryl chlorides are also successful as the coupling partners albeit with lower yields. The methodology is also applicable for theN-arylation of aliphatic primary amines as demonstrated by the reactions of benzylamine with several aryl iodides as well as bromides. The recyclable Pd nanocatalyst catalyzes the reaction by a heterogeneous mechanism, which has been demonstrated by several techniques including the three phase test and thein situICP-MS analysis of the reaction mixture.
Lactam derivatives and preparation method and application thereof
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Paragraph 0048-0052; 0076; 0085, (2020/02/10)
The invention relates to lactam derivatives and a preparation method and application thereof. Compared with the prior art, the invention provides lactam compounds with a novel structure. The compoundsand compositions thereof have remarkable activity in inhibition of the proliferation of cancer cells (including, but not limited to, the liver cancer cell line HepG2 and the lung cancer cell line A549), and the activity of multiple compounds is in the same order of magnitude as the activity of the commercial drug adriamycin or superior to the activity of adriamycin. The compounds of the inventioncan be prepared from N-substituted pyrrole compounds through a reaction, and the preparation method is convenient, rapid and efficient.
Nickel/Photoredox-Catalyzed Methylation of (Hetero)aryl Chlorides Using Trimethyl Orthoformate as a Methyl Radical Source
Kariofillis, Stavros K.,Shields, Benjamin J.,Tekle-Smith, Makeda A.,Zacuto, Michael J.,Doyle, Abigail G.
supporting information, p. 7683 - 7689 (2020/04/22)
Methylation of organohalides represents a valuable transformation, but typically requires harsh reaction conditions or reagents. We report a radical approach for the methylation of (hetero)aryl chlorides using nickel/photoredox catalysis wherein trimethyl orthoformate, a common laboratory solvent, serves as a methyl source. This method permits methylation of (hetero)aryl chlorides and acyl chlorides at an early and late stage with broad functional group compatibility. Mechanistic investigations indicate that trimethyl orthoformate serves as a source of methyl radical via β-scission from a tertiary radical generated upon chlorine-mediated hydrogen atom transfer.
A Co-Cu bimetallic magnetic nanocatalyst with synergistic and bifunctional performance for the base-free Suzuki, Sonogashira, and C-N cross-coupling reactions in water
Allahresani, Ali,Kazemnejadi, Milad,Nasseri, Mohammad Ali,Rezazadeh, Zinat
, p. 10645 - 10660 (2020/09/18)
A novel magnetically recyclable bimetallic catalyst was prepared by anchoring imidazolium moiety and PEG chains on Fe3O4 NPs and named as Fe3O4?PEG/Cu-Co. It was found to be a powerful catalyst for the Sonogashira, Suzuki, and C-N cross-coupling reactions in water as a green solvent without the need for any external base. Fe3O4?PEG/Cu-Co was well characterized with FT-IR, FE-SEM, TEM, VSM, EDX, ICP, UV-visible, CV, and XPS analyses. Optimum ranges of parameters such as time, temperature, and amount of catalyst were investigated by Design-Expert 10.0.7 software for C-C Suzuki, Sonogashira, and C-N cross-coupling reactions to find the optimum conditions. The catalyst was compatible with a variety of aryl halides and N-arenes and gave favorable coupling products with good to high yields for all of them. Hot filtration and Hg poisoning tests involving the nanocatalyst revealed the stability, low metal leaching, and heterogeneous nature of the catalyst. Reaction mechanisms were proposed by study of the UV-visible spectra in situ as well as hydroquinone tests during the progress of reactions. In situ XPS analysis was also used to study the reaction mechanism. To prove the synergistic performance of Co and Cu in the catalyst, its various homologues were synthesized and applied to a model reaction separately, and then their catalytic activities were investigated. Finally, the catalyst could be recovered from the reaction mixture simply, and reused for several cycles with a minimum loss in catalytic activity and performance.
A facile synthesis of 1-aryl pyrroles by clauson-Kaas reaction using oxone as a catalyst under microwave irradiation
Gullapelli, Kumaraswamy,Brahmeshwari,Ravichander
, p. 143 - 148 (2019/03/21)
A new and efficient methodology to synthesize N-substituted pyrrole derivatives by Clauson Kaas reaction employing Oxone as catalyst was developed. The transformation was performed in acetonitrile under microwave irradiation. This procedure has several advantages such as high yield, clean product formation, and short reaction time.
