1963-43-5Relevant academic research and scientific papers
Synthesis method of 2-aromatic acyl pyrrole compounds
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Paragraph 0025-0028; 0069-0072, (2021/06/12)
The invention relates to the field of organic synthesis, and discloses a synthesis method of 2-aromatic acyl pyrrole compounds, wherein the synthesis method comprises the steps: taking an N-aromatic acyl pyrrole compound as a raw material, and carrying ou
Total Synthesis and Antimalarial Activity of 2-(p-Hydroxybenzyl)-prodigiosins, Isoheptylprodigiosin, and Geometric Isomers of Tambjamine MYP1 Isolated from Marine Bacteria
Kancharla, Papireddy,Li, Yuexin,Yeluguri, Monish,Dodean, Rozalia A.,Reynolds, Kevin A.,Kelly, Jane X.
, p. 8739 - 8754 (2021/06/30)
Highly efficient and straightforward synthetic routes toward the first total synthesis of 2-(p-hydroxybenzyl)-prodigiosins (2-5), isoheptylprodigiosin (6), and geometric isomers of tambjamine MYP1 ((E/Z)-7) have been developed. The crucial steps involved in these synthetic routes are the construction of methoxy-bipyrrole-carboxaldehydes (MBCs) and a 20-membered macrocyclic core and a regioselective demethylation of MBC analogues. These new synthetic routes enabled us to generate several natural prodiginines24-27in larger quantity. All of the synthesized natural products exhibited potent asexual blood-stage antiplasmodial activity at low nanomolar concentrations against a panel ofPlasmodium falciparumparasites, with a great therapeutic index. Notably, prodiginines6and24-27provided curative in vivo efficacy against erythrocyticPlasmodium yoeliiat 25 mg/kg × 4 days via oral route in a murine model. No overt clinical toxicity or behavioral change was observed in any mice treated with prodiginines and tambjamines.
Aroylation of Electron-Rich Pyrroles under Minisci Reaction Conditions
Laha, Joydev K.,Kaur Hunjan, Mandeep,Hegde, Shalakha,Gupta, Anjali
, p. 1442 - 1447 (2020/02/22)
The development of Minisci acylation on electron-rich pyrroles under silver-free neutral conditions has been reported featuring the regioselective monoacylation of (NH)-free pyrroles. Unlike conventional Minisci conditions, the avoidance of any acid that could result in the polymerization of pyrroles was the key to success. The umpolung reactivity of the nucleophilic acyl radical, generated in situ from arylglyoxylic acid, could help explain the mechanism of product formation with electron-rich pyrroles. Alternatively, the nucleophilic substitution of the acyl radical on the electron-deficient pyrrole radical cation is proposed.
Method for synthesizing drug intermediate pyrrolidone compound
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Paragraph 0040; 0041; 0042; 0043; 0044, (2016/10/27)
The invention relates to a method for synthesizing a pyrrolidone compound which can be used as a drug intermediate as shown in a formula (III). The method comprises the following steps: reacting a compound as shown in a formula (I) with a compound as shown in a formula (II) in the presence of a catalyst, an organic ligand, an oxidant, an adjuvant and alkali in an organic solvent under a nitrogen atmosphere, and performing post-treatment after the reaction is completed to obtain the compound as shown in the formula (III), wherein R is H, C1-C6 alkyl, C1-C6 alkoxy, halogen or nitro. According to the method, a comprehensive reaction system of catalyst, ligand, oxidant, alkali and solvent is adopted, so that a target product is obtained with high yield. The pyrrolidone compound has an excellent application prospect and industrial production potential in the technical field of organic synthesis, especially drug intermediate synthesis.
Synthesis of 2-benzoylpyrrole derivatives via C-H functionalization adjacent to nitrogen of pyrrole
Guo, Zhiqiang,Wei, Xuehong,Hua, Yupeng,Chao, Jianbin,Liu, Diansheng
, p. 3919 - 3922 (2015/06/08)
A direct transition-metal-free synthesis of 2-benzoylpyrrole derivatives from free (N-H) pyrroles and benzaldehyde has been developed. The benzoylation reaction at the 2 or 5-position of pyrrole proceeded well under the alkali metalation system and with 2
Synthesis of a new compound family, 1-aryl-3H-pyrrolo[2,1-d][1,2,5] triazepin-4(5H)-ones
Milen, Mátyás,ábrányi-Balogh, Péter,Dancsó, András,Simig, Gyula,Volk, Balázs
, p. 465 - 476 (2014/01/06)
Representatives of a new family, 1-aryl-3H-pyrrolo[2,1-d][1,2,5]triazepin- 4(5H)-ones have been synthesized at our laboratory as bioisosters of biologically active 1-aryl-2,3-benzodiazepine-4-ones. The efficient synthetic route described applies the synth
Facile Synthesis of 9,10,19,20-Tetraarylporphycenes
Ganapathi, Emandi,Chatterjee, Tamal,Ravikanth, Mangalampalli
, p. 6701 - 6706 (2016/02/18)
A simple route was developed for the synthesis of 9,10,19,20-tetraarylporphycenes by combining both McMurry and oxidative synthetic strategies and using readily available precursors. The desired 5,6-diaryldipyrroethenes, which were prepared in multigram quantities over two steps, were used to prepare 9,10,19,20-tetraarylporphycenes under mild acid-catalyzed conditions. As 5,6-diaryldipyrroethene precursors can easily be prepared in multigram quantities, this method is useful for the preparation of meso-tetrarylporphycenes that contain different aryl substituents. The molecular structures of these macrocycles were determined by HRMS analysis as well as 1D and 2D NMR studies. The tetraarylporphycenes exhibited a strong Soret band at approximately 380 nm and three Q bands in the region of 580-655 nm. The tetraarylprophycenes are reasonably fluorescent and stable under redox conditions. A simple, rapid method was developed for the synthesis of meso-tetraarylporphycenes by employing a McMurry coupling followed by an oxidation reaction as the key steps. This synthetic strategy uses readily available precursors to afford 9,10,19,20-tetraarylporphycenes. The absorption, fluorescence, and electrochemical properties of these macrocycles were also studied.
Chemoselective reduction of 2-acyl-N-sulfonylpyrroles: Synthesis of 3-pyrrolines and 2-alkylpyrroles
You, Hai Tao,Grosse, Andrew C.,Howard, James K.,Hyland, Christopher J. T.,Just, Jeremy,Molesworth, Peter P.,Smith, Jason A.
experimental part, p. 3948 - 3953 (2011/06/21)
The partial reduction of pyrroles is not a common practice even though it offers a potential route to pyrroline building blocks, commonly used for synthesis. We have investigated the reduction of 2-acyl-N-sulfonylpyrroles and by varying the hydride source
A novel one-pot synthesis of 2-benzoylpyrroles from benzaldehydes
Sharma, Ratnesh,Chouhan, Mangilal,Nair, Vipin A.
experimental part, p. 2039 - 2043 (2010/06/14)
We herein report a novel one-pot reaction for benzoylation of pyrrole. The key step in the reaction is generation of di(1H-pyrrol-1-yl)zirconium(IV) chloride complex which reacts with benzaldehydes and methyl benzoates to give 2-benzoylpyrroles as the major product.
In Situ vinylpyrrole synthesis. Diels-alder reactions with maleimides to give tetrahydroindoles
Noland, Wayland E.,Lanzatella, Nicholas P.,Sizova, Elena P.,Venkatraman, Lakshmanan,Afanasyev, Oleg V.
scheme or table, p. 503 - 534 (2009/09/05)
(Chemical Equation Presented) A series of 108 tetrahydroindoles has been prepared by a one-pot synthesis from 2-alkylpyrroles, cyclic ketones, maleimides, and an acid catalyst. A 5-vinylpyrrole is formed by an acid-catalyzed condensation of a 2-alkyl-substituted pyrrole with a ketone, which is subsequently trapped in situ by a maleimide in a predominantly endo-addition Diels-Alder reaction. Isomerization of the double bond into the pyrrole ring gives a tetrahydroindole with predominant cis-fusion of the cycloalkane ring.
