- Two complementary routes to 7-substituted chlorins. Partial mimics of chlorophyll b
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(Chemical Equation Presented) Chlorophyll a and chlorophyll b exhibit distinct spectra yet differ only in the nature of a single substituent (7-methyl versus 7-formyl, respectively). Two complementary approaches have been developed for the synthesis of 7-
- Muthiah, Chinnasamy,Ptaszek, Marcin,Nguyen, Tien M.,Flack, Kyle M.,Lindsey, Jonathan S.
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Read Online
- Synthesis method of 2-aromatic acyl pyrrole compounds
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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
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Paragraph 0025-0032
(2021/06/12)
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- Extended Multicomponent Reactions with Indole Aldehydes: Access to Unprecedented Polyheterocyclic Scaffolds, Ligands of the Aryl Hydrocarbon Receptor
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The participation of reactants undergoing a polarity inversion along a multicomponent reaction allows the continuation of the transformation with productive domino processes. Thus, indole aldehydes in Groebke–Blackburn–Bienaymé reactions lead to an initial adduct which spontaneously triggers a series of events leading to the discovery of novel reaction pathways together with direct access to a variety of linked, fused, and bridged polyheterocyclic scaffolds. Indole 3- and 4-carbaldehydes with suitable isocyanides and aminoazines afford fused adducts through oxidative Pictet–Spengler processes, whereas indole 2-carbaldehyde yields linked indolocarbazoles under mild conditions, and a bridged macrocycle at high temperature. These novel structures are potent activators of the human aryl hydrocarbon receptor signaling pathway.
- Ghashghaei, Ouldouz,Pedrola, Marina,Seghetti, Francesca,Martin, Victor V.,Zavarce, Ricardo,Babiak, Michal,Novacek, Jiri,Hartung, Frederick,Rolfes, Katharina M.,Haarmann-Stemmann, Thomas,Lavilla, Rodolfo
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supporting information
p. 2603 - 2608
(2020/11/30)
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- Selective PdII-Catalyzed Acylation of Pyrrole with Aldehydes. Application to the Synthesis of Celastramycin Analogues and Tolmetin
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The PdII-catalyzed C-2 acylation of pyrrole with aldehydes in the presence of TBHP as oxidant has been studied for the synthesis of di(hetero)aryl ketones. The use of 2-pyrimidine as directing group leads to 2-acylpyrroles in moderate to good yields, although 2,5-diacylpyrroles are obtained as by products. This side-reaction could be avoided using 3-methy-2-pyridine as directing group, obtaining selectively 2-acylpyrroles. The reaction has been extended to a series of aromatic and heteroaromatic aldehydes, obtaining the best results with electron rich aromatic aldehydes. The methodology has been applied in the synthesis of pyrrolomycin alkaloid Celastramycin analogues and for an improved synthesis of Tolmetin, a nonsteroidal anti-inflammatory drug.
- Santiago, Carlos,Rubio, Ibon,Sotomayor, Nuria,Lete, Esther
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p. 4284 - 4295
(2020/05/25)
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- Aroylation of Electron-Rich Pyrroles under Minisci Reaction Conditions
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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.
- Laha, Joydev K.,Kaur Hunjan, Mandeep,Hegde, Shalakha,Gupta, Anjali
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p. 1442 - 1447
(2020/02/22)
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- Method for synthesizing drug intermediate pyrrolidone compound
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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.
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Paragraph `0045; 0046; 0047; 0048; 0049
(2016/10/27)
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- Synthesis of 2-benzoylpyrrole derivatives via C-H functionalization adjacent to nitrogen of pyrrole
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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
- Guo, Zhiqiang,Wei, Xuehong,Hua, Yupeng,Chao, Jianbin,Liu, Diansheng
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p. 3919 - 3922
(2015/06/08)
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- Facile Synthesis of 9,10,19,20-Tetraarylporphycenes
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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.
- Ganapathi, Emandi,Chatterjee, Tamal,Ravikanth, Mangalampalli
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p. 6701 - 6706
(2016/02/18)
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- Acylation of pyrroles and their free (N-H)-derivatives via palladium-catalyzed carbopalladation of nitriles
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An efficient regioselective synthesis of 2-acylpyrroles via palladium-catalyzed addition of pyrroles with benzonitriles and subsequent hydrolysis is developed. The direct acylation reaction of protected as well as (NH)-free pyrroles proceeded smoothly to
- Jafarpour, Farnaz,Hazrati, Hamideh,Darvishmolla, Masoumeh
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supporting information
p. 3784 - 3788
(2015/02/19)
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- A novel one-pot synthesis of 2-benzoylpyrroles from benzaldehydes
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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.
- Sharma, Ratnesh,Chouhan, Mangilal,Nair, Vipin A.
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experimental part
p. 2039 - 2043
(2010/06/14)
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- In Situ vinylpyrrole synthesis. Diels-alder reactions with maleimides to give tetrahydroindoles
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(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.
- Noland, Wayland E.,Lanzatella, Nicholas P.,Sizova, Elena P.,Venkatraman, Lakshmanan,Afanasyev, Oleg V.
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scheme or table
p. 503 - 534
(2009/09/05)
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- Ketopyrroles useful as ligands in organic iridium compositions
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The present invention provides novel ketopyrroles having structure XXIV wherein R2 is independently at each occurrence a deuterium atom, a halogen, a nitro group, an amino group, a C3-C40 aromatic radical, a C1-C50 aliphatic radical, or a C3-C40 cyclcoaliphatic radical; “a” is an integer from 0 to 3; and X1 and X2 are independently at each occurrence a bromine atom, a hydroxy group, or the group OR10, and wherein the group R10 is independently at each occurrence a deuterium atom, a halogen, a nitro group, an amino group, a C3-C40 aromatic radical, a C1-C50 aliphatic radical, or a C3-C40 cyclcoaliphatic radical. Ketopyrroles XXIV are useful ligands for the preparation of Type (1) and Type (2) organic iridium compositions. In one aspect, the present invention provides deuterated analogs of XXIV. Organic iridium compositions are useful in the preparation optoelectronic devices, such as OLED devices and photovoltaic devices exhibiting enhanced performance characteristics.
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Page/Page column 36
(2008/06/13)
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- NOVEL HETEROARYL DERIVATIVE
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A compound of the following formula (1), or its prodrug or pharmaceutically acceptable salt thereof, being useful as a diabetic medicine or preventive, or blood sugar regulator, or therapeutic agent for hyperlipemia, etc. wherein the ring Z is an optionally substituted heteroaryl, W4 is a single bond, lower alkylene, etc., Ar2 is an optionally substituted aryl, etc., W3 is a single bond, lower alkylene, etc., Ar1 is an optionally substituted arylene, etc., each of W1 and W2 is an optionally substituted lower alkylene, etc., and R1 is carboxyl, an alkoxycarbonyl.
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- NOVEL HETEROARYL DERIVATIVE
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A heteroaryl derivative of the formula (1): (wherein Ring Z is an optionally substituted heteroaryl, R1 is a carboxyl group or an alkoxycarbonyl group, etc., W1 and W2 are an optionally substituted lower alkylene, Ar1 is an optionally substituted arylene or an optionally substituted heteroarylene, W3 is a single bond, a lower alkylene, a lower alkenylene, etc., W4 is a single bond, -NR10-, etc., Ar2 is an optionally substituted aryl or an optionally substituted heteroaryl), or a prodrug thereof, or a pharmaceutically acceptable salt thereof.
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Page/Page column 26
(2008/06/13)
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- NOVEL HETEROARYL DERIVATIVE
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A compound of the following formula (1), or its prodrug or pharmaceutically acceptable salt thereof, being useful as a diabetic medicine or preventive, or blood sugar regulator, or therapeutic agent for hyperlipemia, etc. (1) wherein: the ring Z is an optionally substituted heteroaryl, W4 is a single bond, lower alkylene, etc., Ar2 is an optionally substituted aryl, etc., W3 is a single bond, lower alkylene, etc., Ar1 is an optionally substituted arylene, etc., each of W1 and W2 is an optionally substituted lower alkylene, etc., and R1 is carboxyl, an alkoxycarbonyl, etc.
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Page/Page column 60
(2008/06/13)
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- Vilsmeier-Haack preparation of 2-acylpyrroles using bis(trichloromethyl) carbonate and N,N-dimethylacylamines
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A series of 2-acylpyrroles were synthesized by using bis(trichloromethyl) carbonate and N,N-dimethylacylamines as Vilsmeier-Haack reagents under mild conditions in good yields.
- Shi,Su,Shan
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p. 1019 - 1021
(2007/10/03)
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- FIBROSIS INHIBITOR
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Medicament being useful as a fibrosis inhibitor for organs or tissues, which comprises a compound of the formula (I): wherein Ring Z is optionally substituted pyrrole ring, etc.; W2 is -CO-, -SO2-, optionally substituted C1-C4 alkylene, etc.; Ar2 is optionally substituted aryl, etc.; W1 and Ar1 mean the following (1) and (2):(1) W1 is optionally substituted C1-C4 alkylene, etc.; Ar1 is optionally substituted bicyclic heteroaryl having 1 to 4 nitrogen atoms as ring-forming atoms:(2) W1 is optionally substituted C2-C5 alkylene, optionally substituted C2-C5 alkenylene, etc.; and Ar1 is aryl or monocyclic heteroaryl, which is substituted by carboxyl, alkoxycarbonyl, etc. at the ortho- or meta-position thereof with respect to the binding position of W1, or a pharmaceutically acceptable salt thereof.
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- PYRROLE DERIVATIVE
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A novel pyrrole derivative represented by the following formula (1) and a salt thereof: wherein R1 means substituted alkenyl, etc.; R2 means substituted benzoyl, etc.; and R3 to R5 each means hydrogen, alkyl, halogeno, etc. The derivative and salt have antidiabetic activity.
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- Infrared and Nuclear Magnetic Resonance Properties of Benzoyl Derivatives of Five-membered Monoheterocycles and Determination of Aromaticity Indices
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Benzophenones, 2-benzoylthiophenes, 2-benzoylpyrroles, and 2-benzoylfurans, which have substituents at m- and p-positions of the benzoyl ring were prepared and their ir and nmr spectra were obtained in 0.1 M chloroform-d solution. The chemical shift values of each series were plotted against the Hammett substituent parameters to give good correlation, with the exception of the ortho-Hs and -Cs. The slopes as well as the differences in chemical shift gave sets of meaningful values for the indices of aromaticy.
- Jeon, Kyu Ok,Jun, Jung Ho,Yu, Ji Sook,Lee, Chang Kiu
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p. 763 - 771
(2007/10/03)
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- Regiospecific C-acylation of pyrroles and indoles using N-acylbenzotriazoles
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Reactions of pyrrole (2) or 1-methylpyrrole (4) with readily available N-acylbenzotriazoles 1a - g (RCOBt, where R = 4-tolyl, 4-nitrophenyl, 4-diethylaminophenyl, 2-furyl, 2-pyridyl, 2-indolyl, or 2-pyrrolyl) in the presence of TiCl4 produced 2
- Katritzky, Alan R.,Suzuki, Kazuyuki,Singh, Sandeep K.,He, Hai-Ying
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p. 5720 - 5723
(2007/10/03)
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- Pyrrole derivatives
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Pyrrole derivatives represented by the following formula: wherein Ring Z is an optionally substituted pyrrole ring, etc.; W2 is —CO—, —SO2—, an optionally substituted C1-C4 alkylene, etc.; Ar2 is an optionally substituted aryl, etc.; W2 and Ar1 mean the following (1) and (2): (1) W1 is an optionally substituted C1-C4 alkylene, etc.; Ar1 is an optionally substituted bicyclic heteroaryl having 1 to 4 nitrogen atoms as ring-forming atoms: (2) W1 is an optionally substituted C2-C5 alkylene, an optionally substituted C2-C5 alkenylene, etc.; and Ar1 is an aryl or monocyclic heteroaryl, which are substituted by carboxyl, an alkoxycarbonyl, etc. at the ortho- or meta-position thereof with respect to the binding position of W1, or a pharmaceutically acceptable salt thereof These compounds are useful as medicaments such as a fibrosis inhibitor for organs or tissues.
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- Antifungal agents, II: Synthesis and antifungal activities of aryl-1H-pyrrol-2-yl-1H-imidazol-1-yl-methane derivatives with unsaturated chains
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The synthesis and antifungal activities of aryl-1H-pyrrol-2-yl-1H-imidazol-1-yl-methanes having allyl, crotyl, and acrylate chains linked to the N-pyrrole atom and substituted at phenyl ring by Cl, F, CH3, and NO2 groups are reported
- Massa,Ragno,Porretta,Mai,Retico,Artico,Simonetti
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p. 539 - 546
(2007/10/02)
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- 2-SUBSTITUTED 1,3-BENZODITHIOLIUM TETRAFLUOROBORATES AS USEFUL ACYLATING AGENTS OF PYRROLE
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A comparative study on the acylation of pyrrole by utilizing 2-substituted 1,3-benzodithiolium tetrafluoroborates instead of 2-substituted 1,3-benzoxathiolium tetrafluoroborates has been accomplished.The use of 2-substituted 1,3-benzodithiolium tetrafluoroborates proved to be more convenient since it gives higher yields of 2-acylpyrroles (58-90percent) and appears of larger applicability for the preparation of symmetrical and unsymmetrical 2,5-diacylpyrroles which were obtained in most cases in quantitative yields.
- Barbero, Margherita,Cadamuro, Silvano,Degani, Iacopo,Dughera, Stefano,Fochi, Rita,et al.
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p. 619 - 627
(2007/10/02)
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