- Condensation reactions of a nitrodienamine with organocopper and alkyllithium reagents prepared from pyrrole derivatives
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Condensation reactions of a nitrodienamine (1) with Grignard, organocopper and alkyllithium reagents prepared from pyrrole derivatives were investigated.
- Koike, Takeshi,Shinohara, Yoshifumi,Nishimura, Takeshi,Hagiwara, Masanori,Tobinaga, Seisho,Takeuchi, Naoki
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Read Online
- Catalytic, Interrupted Formal Homo-Nazarov Cyclization with (Hetero)arenes: Access to α-(Hetero)aryl Cyclohexanones
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The first examples of a Lewis-acid catalyzed (hetero)arene interrupted, formal homo-Nazarov cyclization have been disclosed. Using SnCl4 as the catalyst, alkenyl cyclopropyl ketones undergo ring-opening cyclization to form six-membered cyclic oxyallyl cations. Subsequent intermolecular Friedel-Crafts-type arylation with various electron-rich arenes and heteroarenes provides functionalized α-(hetero)arylated cyclohexanones, a scaffold present in many natural products and bioactive compounds, in yields up to 88% and diastereomeric ratios up to 12:1. Regiospecific arylation occurs at the α-carbon of the oxyallyl cation due to polarization caused by the ester group.
- Williams, Corey W.,Shenje, Raynold,France, Stefan
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Read Online
- Primary Sulfonamide Functionalization via Sulfonyl Pyrroles: Seeing the N?Ts Bond in a Different Light
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Despite common occurrence in molecules of value, methods for transforming sulfonamides are distinctly lacking. Here we introduce easy-to-access sulfonyl pyrroles as synthetic linchpins for sulfonamide functionalization. The versatility of the sulfonyl pyrrole unit is shown by generating a variety of products through chemical, electrochemical and photochemical pathways. Preliminary results on the direct functionalization of primary sulfonamides are also provided, which may lead to new modes of activation.
- Ozaki, Tomoya,Yorimitsu, Hideki,Perry, Gregory J. P.
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supporting information
p. 15387 - 15391
(2021/10/04)
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- Synthesis of a New Phorbazole and Its Derivatives
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Phorbazoles are chlorinated marine alkaloids containing pyrrole, oxazole and phenol ring units, and differ in the number and positions of chlorine atoms. They are isolated from sea sponges and nudibranchs. In this work, a convenient synthetic method leading to a new phorbazole and its derivatives is developed. This synthesis of synthetic phorbazole G and its derivatives is achieved in seven steps in good overall yields of 26-52%. It involves formation of the pyrrole-oxazole skeleton followed by chlorination. The pyrrole-oxazole skeleton is synthesized from pyrrole and substituted acetophenones, and the key step involves cyclodehydration of amide intermediates to give protected oxazoles, followed by hydrolysis.
- Louglin, Wendy A.,Muderawan, I Wayan,Young, David J.
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- Pyrrole Hemithioindigo Antimitotics with Near-Quantitative Bidirectional Photoswitching that Photocontrol Cellular Microtubule Dynamics with Single-Cell Precision**
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We report the first cellular application of the emerging near-quantitative photoswitch pyrrole hemithioindigo, by rationally designing photopharmaceutical PHTub inhibitors of the cytoskeletal protein tubulin. PHTubs allow simultaneous visible-light imaging and photoswitching in live cells, delivering cell-precise photomodulation of microtubule dynamics, and photocontrol over cell cycle progression and cell death. This is the first acute use of a hemithioindigo photopharmaceutical for high-spatiotemporal-resolution biological control in live cells. It additionally demonstrates the utility of near-quantitative photoswitches, by enabling a dark-active design to overcome residual background activity during cellular photopatterning. This work opens up new horizons for high-precision microtubule research using PHTubs and shows the cellular applicability of pyrrole hemithioindigo as a valuable scaffold for photocontrol of a range of other biological targets.
- Akhmanova, Anna,Heise, Constanze,Meiring, Joyce C. M.,Pettersson, Linda N.,Sailer, Alexander,Thorn-Seshold, Julia,Thorn-Seshold, Oliver
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supporting information
p. 23695 - 23704
(2021/10/05)
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- Paramagnetic calix[4]porphyrin compound and preparation method thereof
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The invention discloses a paramagnetic calix[4]porphyrin compound and a preparation method thereof. Monopyrrole is used as a starting raw material, an electron-rich pyrene group is introduced to a beta position of the monopyrrole to obtain 3-pyrenyl pyrro
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Paragraph 0029; 0034; 0038
(2020/11/09)
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- Transition-Metal-Free and Visible-Light-Mediated Desulfonylation and Dehalogenation Reactions: Hantzsch Ester Anion as Electron and Hydrogen Atom Donor
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Novel approaches for N- and O-desulfonylation under room temperature (rt) and transition-metal-free conditions have been developed. The first methodology involves the transformation of a variety of N-sulfonyl heterocycles and phenyl benzenesulfonates to the corresponding desulfonylated products in good to excellent yields using only KOtBu in dimethyl sulfoxide (DMSO) at rt. Alternately, a visible light method has been used for deprotection of N-methyl-N-arylsulfonamides with Hantzsch ester (HE) anion serving as the visible-light-absorbing reagent and electron and hydrogen atom donor to promote the desulfonylation reaction. The HE anion can be easily prepared in situ by reaction of the corresponding HE with KOtBu in DMSO at rt. Both protocols were further explored in terms of synthetic scope as well as mechanistic aspects to rationalize key features of desulfonylation processes. Furthermore, the HE anion induces reductive dehalogenation reaction of aryl halides under visible light irradiation.
- Heredia, Micaela D.,Guerra, Walter D.,Barolo, Silvia M.,Fornasier, Santiago J.,Rossi, Roberto A.,Budén, Mariá E.
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supporting information
p. 13481 - 13494
(2020/12/15)
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- Synthesis of 3-hetarylpyrroles by Suzuki–Miyaura cross-coupling
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1-[tert-Butyl(diphenyl)silyl]pyrrol-3-ylboronic acid was obtained from pyrrole in three steps. Its Suzuki–Miyaura cross-coupling with functionalized pyridinyl and pyrimidinyl bromides afforded new promising 3-hetaryl-1H-pyrroles.
- Khandazhinskaya, Anastasia L.,Kochetkov, Sergey N.,Matyugina, Elena S.,Seley-Radtke, Katherine L.
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p. 231 - 232
(2020/05/25)
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- Synthesis of N -Sulfonyl- and N -Acylpyrroles via a Ring-Closing Metathesis/Dehydrogenation Tandem Reaction
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N -Sulfonyl- and N -acylpyrroles were synthesized via olefin ring-closing metathesis of diallylamines and in situ oxidative aromatization in the presence of the ruthenium Grubbs catalyst and a suitable copper catalyst. In the presence of Cu(OTf) 2/s
- Chen, Weiqiang,Li, Hui-Jing,Liu, Ying,Nan, Xiang,Wu, Yan-Chao,Zhang, Yin-Lin
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p. 3651 - 3666
(2019/09/30)
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- Rh(II)-Catalyzed Monocyclopropanation of Pyrroles and Its Application to the Synthesis Pharmaceutically Relevant Compounds
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Here we report Rh(II)-catalyzed monocyclopropanation reactions on pyrroles in the presence of aryldiazoacetates, providing the corresponding dearomatized products with high levels of enantioselectivity (up to >99% ee). Under the catalysis of Rh2/sub
- Fu, Jiantao,Wurzer, Nikolai,Lehner, Verena,Reiser, Oliver,Davies, Huw M. L.
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supporting information
p. 6102 - 6106
(2019/08/26)
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- Mild alkaline hydrolysis of hindered esters in non-aqueous solution
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Sterically hindered esters of carboxylic acids, which are considered very resistant to saponification, were rapidly and efficiently saponified in a non-aqueous medium using NaOH in MeOH/CH2Cl2 (1:9) at room temperature. Furthermore, this reaction protocol was extended and successfully applied to the hydrolysis of tosylates and N-tosyl indoles.
- Theodorou, Vassiliki,Alagiannis, Michalis,Ntemou, Nikoleta,Brentas, Alexios,Voulgari, Pinelopi,Polychronidou, Vasiliki,Gogou, Marina,Giannelos, Marios,Skobridis, Konstantinos
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p. 308 - 319
(2018/11/26)
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- Asymmetric Organocatalytic Synthesis of Bisindoles – Scope and Derivatizations
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Starting from 3-vinylindoles and glyoxolate imines, we created a library of diverse 4,6-bis(1H-indole-3-yl)piperidine 2-carboxylates by using 10 mol-% of a chiral phosphoric acid. Utilising electron-withdrawing groups on the starting material during the r
- Retich, Christina,Br?se, Stefan
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supporting information
p. 60 - 77
(2018/01/17)
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- Synthesis of (±)-γ-Lycorane by Using an Intramolecular Friedel-Crafts Reaction
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A total synthesis of γ-lycorane has been achieved by employing N -tosylpyrrole as a key building block. The synthesis employs both an intermolecular and an intramolecular Friedel-Crafts reaction, as well as a completely diastereoselective hydrogenation of
- Doan, Bao Nguyen Do,Tan, Xin Yi,Ang, Chin May,Bates, Roderick W.
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supporting information
p. 4711 - 4716
(2017/10/06)
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- Palladium-Catalyzed Regioselective Dehydrogenative C–H/C–H Cross-Coupling of Pyrroles and Pyridine N-Oxides
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The palladium-catalyzed cross-dehydrogenative coupling of N-alkylpyrroles and pyridine N-oxides gave the corresponding pyrrolylpyridine N-oxides. Cu(OAc)2·H2O as a co-catalyst with air as the terminal oxidant led to preferential coupling in the β-position, whereas AgOAc as the stoichiometric oxidant resulted in preferential coupling in the α-position. N-(Benzyloxymethyl)pyrrole derivatives were deprotected by hydrogenolysis followed by basic hydrolysis.
- Liu, Shanshan,Tzschucke, C. Christoph
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supporting information
p. 3509 - 3513
(2016/07/28)
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- Highly efficient preparation of amides from aminium carboxylates using N-(p-toluenesulfonyl) imidazole
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Treatment of aminium carboxylates with N-(p-toluenesulfonyl)imidazole in the presence of triethylamine in DMF at 100 °C afforded the corresponding amides in good to excellent yields. N-(p-Toluenesulfonyl)imidazole proved to be a highly efficient coupling reagent for the preparation of numerous structurally diverse primary, secondary and tertiary amides.
- Behrouz, Somayeh,Rad, Mohammad Navid Soltani,Forouhari, Elham
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p. 101 - 106
(2016/03/08)
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- P2X4 RECEPTOR MODULATING COMPOUNDS
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Provided herein are P2X4 receptor modulating compounds, methods of their synthesis, pharmaceutical compositions comprising the compounds, and methods of their use. The compounds provided herein are useful for the treatment, prevention, and/or management of various disorders, including but not limited to, chronic pain, neuropathy, inflammatory diseases and central nervous system disorders.
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Paragraph 00239
(2015/06/25)
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- COMPOUNDS USEFUL AS MODULATORS OF TRPM8
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The present invention includes compounds useful as modulators of TRPM8, such as compounds of Formulae (Ia), (Ib) and (Ic), and the subgenus and species thereof; personal products containing those compounds; and the use of those compounds and the personal products, particularly the use of increasing or inducing chemesthetic sensations, such as cooling or cold sensations.
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Paragraph 0922
(2016/03/29)
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- Copper-catalyzed domino homologation and cycloisomerization reactions for 3-pyrroline synthesis
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Copper bromide was found to be an efficient catalyst for a domino reaction sequence leading to 3-pyrrolines. The Cu(I)-catalyzed Crabbe reaction of propargyl sulfonamide and selective cycloisomerization of the allene intermediate were carried out using microwave irradiation conditions affording a wide range of 2-substituted- and 2,5-disubstituted-3-pyrrolines. Mechanistic studies of the reaction intermediates revealed two possible reaction pathways; both invoke the importance of vinyl copper intermediates.
- Shin, Ye Ho,Maheswara, Muchchintala,Hwang, Joon Young,Kang, Eun Joo
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p. 2305 - 2311
(2014/04/17)
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- Modular access to complex prodiginines: Total synthesis of (+)-roseophilin via its 2-azafulvene prototropisomer
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Ansa-bridged prodiginines are bioactive pigments produced by bacteria. Certain of these structures are reported to be antagonists of protein-protein interactions involved in apoptosis. We describe a new entry to alkaloids of this type, demonstrated with a concise asymmetric synthesis of (+)-roseophilin (3). Our route constructs the pyrrolophane motif via phosphoryl transfer-terminated macroaldolization and passes through a previously unexplored prototropic form of the natural product.
- Frederich, James H.,Harran, Patrick G.
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supporting information
p. 3788 - 3791
(2013/04/10)
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- A novel necroptosis inhibitor - Necrostatin-21 and its SAR study
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An initial structure-activity relationship study of the novel necroptosis inhibitor Nec-21 was described. Any changes of the tetracyclic scaffold were detrimental for the activity. Introduction of a substituent to 7 or 8 position (e.g., cyano or methoxy group, respectively), would increase the activity. The 7 and 8-position disubstituted compound 17b was 35-fold as potent as the lead, while EC50 reached 14 nM.
- Wu, Zhijie,Li, Ying,Cai, Yu,Yuan, Junying,Yuan, Chengye
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supporting information
p. 4903 - 4906
(2013/09/02)
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- Assisted tandem catalytic RCM-aromatization in the synthesis of pyrroles and furans
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An assisted tandem catalytic transformation of diallyl amines and diallyl ethers into N-aryl pyrroles and furans, respectively, is described. The sequence relies on ring closing metathesis followed by dehydrogenation of the initially formed dihydropyrroles and dihydrofurans. Both steps are Ru-catalyzed, but the sequence requires only one precatalyst, because conversion of the metathesis catalyst into the dehydrogenation catalyst is achieved in situ, triggered by the oxidant tert-butyl hydroperoxide.
- Schmidt, Bernd,Krehl, Stefan,Jablowski, Eric
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supporting information; experimental part
p. 5119 - 5130
(2012/08/07)
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- Cross metathesis of N-allylamines and α,β-unsaturated carbonyl compounds: A one-pot synthesis of substituted pyrroles
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A tandem reaction involving cross metathesis followed by concomitant cyclisation has been developed for the synthesis of substituted pyrroles. Various protected electron-deficient N-allylamines reacted with α,β-unsaturated carbonyl compounds in the presen
- Shafi, Syed,K?dziorek, Mariusz,Grela, Karol
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supporting information; experimental part
p. 124 - 128
(2011/03/20)
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- Total synthesis of (±)-marinopyrrole a via copper-mediated N-arylation
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The total synthesis of the racemic form of the marine alkaloid marinopyrrole A is described. The characteristic 1,3′-bipyrrole core was constructed by a copper-mediated N-arylation process under microwave irradiation.
- Kanakis, Argyrios A.,Sarli, Vasiliki
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supporting information; experimental part
p. 4872 - 4875
(2011/02/22)
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- Scandium triflate-catalysed synthesis of N-substituted pyrroles from amine and 2,5-dimethoxytetrahydrofuran
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The Clauson-Kass pyrrole synthesis catalysed by scandium triflate afforded N-substituted 2- and 3-unsubstituted pyrroles with yields ranged from good to excellent. Aromatic amines, heteroaomatic amines, 4-methylbenzenesulfonamide and 2-chlorobenzamide are good substrates in this transformation.
- Zuo, Bing,Chen, Jiuxi,Liu, Miaochang,Ding, Jinchang,Wu, Huayue,Su, Weike
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experimental part
p. 14 - 16
(2009/09/25)
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- A microwave-assisted, green procedure for the synthesis of N-aryl sulfonyl and N-aryl pyrroles
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A simplified approach to the uncatalyzed Paal-Knorr condensation using microwave irradiation in water is described.
- Wilson, Matthew A.,Filzen, Gary,Welmaker, Gregory S.
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experimental part
p. 4807 - 4809
(2009/10/26)
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- Iron-catalyzed inexpensive and practical synthesis of N-substituted pyrroles in water
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An operationally simple, practical, and economical protocol for iron(III) chloride catalyzed Paal-Knorr pyrrole synthesis in water in good to excellent yields has been developed. Several N-substituted pyrroles are readily prepared from the reaction of 2,5-dimethoxytetrahydrofuran and aryl/alkyl, sulfonyl and acyl amines under very mild reaction conditions. Georg Thieme Verlag Stuttgart.
- Azizi, Najmedin,Khajeh-Amiri, Alireza,Ghafuri, Hossein,Bolourtchian, Mohammad,Saidi, Mohammad Reza
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experimental part
p. 2245 - 2248
(2009/12/03)
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- Access to indoles via Diels-Alder reactions of 3-vinylpyrroles
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(Chemical Equation Presented) N-p-Toluenesulfonyl-3-vinylpyrrole underwent endo-addition [4 + 2] cycloaddition reactions with maleimides and benzoquinones, followed by isomerization to give tetrahydroindoles in good yields. Dehydrogenation with activated MnO2 in refluxing toluene gave the corresponding indoles in fair to good yields. Detosylation via saponification or with magnesium in refluxing methanol gave the N-H indoles in moderate to good yields. This method for formation of indoles is both convergent and versatile and uses starting materials that are conveniently prepared.
- Noland, Wayland E.,Lanzatella, Nicholas P.
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scheme or table
p. 1285 - 1295
(2010/03/23)
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- Synthesis of new pyrrolobenzazepines via Pictet-Spengler cyclization
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A new six-step divergent strategy was developed allowing access to pyrrolobenzazepine structures from pyrrole. This strategy was based on a regioselective Friedel-Crafts acylation followed by a Pictet-Spengler cyclization. Georg Thieme Verlag Stuttgart.
- Gracia, Stéphanie,Schulz, Jürgen,Pellet-Rostaing, Stéphane,Lemaire, Marc
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scheme or table
p. 1852 - 1856
(2009/04/07)
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- Triflic acid controlled successive annelation of aromatic sulfonamides: an efficient one-pot synthesis of N-sulfonyl pyrroles, indoles and carbazoles
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A novel one-pot synthesis of N-substituted heterocycles via successive cyclization/annelation starting from primary sulfonamides is described. This process directly leads to N-sulfonyl pyrroles, indoles and carbazoles. The selection of an appropriate reac
- Abid, Mohammed,Teixeira, Liliana,T?r?k, Béla
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p. 4047 - 4050
(2008/02/02)
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- Synthesis and polymerisation of α,ω-bis(3-pyrrolyl)alkanes
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The synthesis, characterisation and polymerisation studies of a homologous series of α,ω-bis(pyrrolyl)alkanes are described. These α,ω-bis(pyrrolyl)alkanes were produced using Friedel-Crafts acylation followed by reduction of the carbonyl group using Red-
- Foitzik, Richard C.,Kaynak, Akif,Pfeffer, Frederick M.
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p. 4237 - 4242
(2007/10/03)
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- Efficient sulfonation of 1-phenylsulfonyl-1H-pyrroles and 1-phenylsulfonyl-1H-indoles using chlorosulfonic acid in acetonitrile
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The sulfonation of various 1-phenylsulfonyl-1H-pyrroles and 1-phenylsulfonyl-1H-indoles using chlorosulfonic acid in acetonitrile has been studied, leading to the development of a clean and operationally simple protocol allowing direct synthesis of the corresponding 1-phenylsulfonyl-1H-pyrrole-3- sulfonyl chlorides and 1-phenylsulfonyl-1H-indole-3-sulfonyl chlorides, respectively, both of which may be easily converted to various sulfonamide derivatives by treatment with nitrogen nucleophiles. Efficient and selective removal of the phenylsulfonyl- or tosyl groups in the sulfonamide series may be achieved under mild conditions.
- Janosik, Tomasz,Shirani, Hamid,Wahlstr?m, Niklas,Malky, Ilham,Stensland, Birgitta,Bergman, Jan
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p. 1699 - 1707
(2007/10/03)
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- Pyrroles substituted by oligonucleotides
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The invention relates to novel pyrrole derivatives of the formula (I) which make it possible to immobilize and address oligonucleotides by electropolymerization. Said invention also relates to thus produced electroactive polymers and to methods for using
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Page/Page column 10
(2008/06/13)
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- Investigations into the parallel synthesis of novel pyrrole-oxazole analogues of the insecticide pirate
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Investigations into the parallel synthesis of selected analogues of a structurally unique pyrrole-oxazole analogue of the pyrrole insecticide pirate, are reported. Acylaminoketone salts were obtained from ketobromides in moderate to high yields and excell
- Loughlin, Wendy A.,Henderson, Luke C.,Elson, Kathryn E.,Murphy, Michelle E.
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p. 1975 - 1980
(2007/10/03)
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- A metathesis approach to aromatic heterocycles
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The ring closing metathesis (RCM) reaction can be used to prepare substituted furans and pyrroles. By utilising a Pd-catalysed coupling reaction with methoxyallene, allylic alcohols and sulfonamides can be converted into substrates that are ideal precursors to ring closing metathesis. After the RCM reaction is complete, the addition of acid promotes an elimination of methanol to form the fully aromatised system. A range of different substitution patterns and functional groups are compatible with this sequence. Double allene coupling, RCM and elimination reactions are also possible and allow the formation of biaryl systems. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005.
- Donohoe, Timothy J.,Orr, Allan J.,Gosby, Katherine,Bingham, Matilda
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p. 1969 - 1971
(2007/10/03)
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- The pyrrole approach toward the synthesis of fully functionalized cup-shaped molecules
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(Chemical Equation Presented) A novel method for the synthesis of new highly functionalized cyclotrimers is described. The method consists of an original synthesis of β-dibromosubstituted pyrroles, metalation, cycloaddition, and cyclotrimerization. The se
- Zonta, Cristiano,Fabris, Fabrizio,De Lucchi, Ottorino
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p. 1003 - 1006
(2007/10/03)
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- Synthesis of a novel pyrrole oxazole analogue of the insecticide pirate
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The pyrrole oxazole 4 is a novel analogue of the broad-spectrum insecticide and miticide pirate 2. The expedient synthesis of pyrrole oxazole 4 in six steps from pyrrole is reported using a synthetic route that could have potential for the solution-phase
- Loughlin, Wendy A.,Murphy, Michelle E.,Elson, Kathryn E.,Henderson, Luke C.
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p. 227 - 232
(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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- Organic reactions in ionic liquids: A simple and highly regioselective N-substitution of pyrrole
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In ionic liquids [Bmim][PF6] or [Bmim][BF4], pyrrole replaced the halogen atom of an alkyl halide to give the corresponding N-substituted pyrrole in excellent yield. Benzenesulfonyl chloride, p-methylbenzenesulfonyl chloride and benzoyl chloride reacted similarly with pyrroles to afford the N-substituted pyrroles in quantitative yield. Michael addition reaction of pyrrole with electrophilic olefins was completed in a highly regioselective manner to afford the N-alkylpyrroles.
- Le, Zhang-Gao,Chen, Zhen-Chu,Hu, Yi,Zheng, Qin-Guo
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p. 1951 - 1954
(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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- Synthesis and properties of polyquinolines and polyanthrazolines containing pyrrole units in the main chain
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A series of eight new polyquinolines and polyanthrazolines with pyrrole isomeric units in main chain were synthesized and characterized. The new polymers showed high glass transition temperatures (Tg = 242-339°C) and excellent thermal stability (T5% = 398-536°C in air, TGA). Compared to the series of polyanthrazolines, the series of polyquinolines exhibited higher thermal stability, better solubility in common organic solvents, and lower maximum absorption wavelengths (λmaxa). Polyanthrazolines with 2,5-pyrrole linkage showed an unusually high λmaxa (565 nm) and small band gap (2.02 eV). All polymers in solution had low photoluminescence quantum yields between 10-2% and 10-5% and excited-state lifetimes of 0.28-1.29 ns. The effects of molecular structure, especially pyrrole linkage structures, on the electronic structure, thermodynamics, and some of the optical properties of the polymers were explored. A model of hydrogen bonds in the main chain of the polymers was suggested to explain the difference in the properties of the isomer polymers. In addition, a polyquinoline (PBM) was chosen to examine the proton conductivity; the result indicated that the PBM/H3PO4 complex exhibited a high conductivity of 1.5 × 10-3 S cm-1 at 157°C. The new polymers are expected to have improved proton-conducting properties for the application as the membranes in fuel cells.
- Hou, Shifa,Ding, Mengxian,Gao, Lianxun
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p. 3826 - 3832
(2007/10/03)
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- New Photocleavable Structures I: Synthesis of Hydroxyalkylphenone Analogues Electron-rich Heterocycles
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A series of photoinitiating compounds with the general structure ArCOCMe2OH, where Ar is 2-furyl (1a), 3-furyl (1b), 2-thienyl (2a), 3-thienyl (2b), 2-pyrrolyl (3a) and 3-pyrrolyl (3b), were prepared. The heterocyclic precursors were substituted by Friede
- Liska, Robert
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p. 1475 - 1486
(2007/10/03)
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- Studies towards the synthesis of phorbazoles A-D: Formation of the pyrrole oxazole skeleton
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Synthetic approaches towards the synthesis of the pyrrole oxazole skeleton of phorbazoles A-D are described. An efficient synthesis of the pyrrole oxazole skeleton (19) from pyrrole and 4-methoxyacetophenone was developed. In the key step, cyclodehydratio
- Loughlin, Wendy A.,Muderawan, I. Wayan,McCleary, Michelle A.,Voller, Katie E.,King, Malcolm D.
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p. 231 - 234
(2007/10/03)
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- Design of chiral poly(pyrroles)
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The synthesis of three 3-substituted and one N-substituted chiral pyrrole derivatives as well as their electropolymerization conditions are described. The new materials thus obtained possess recognition properties as enantioselective electrodes.
- Pleus, Susanne,Schwientek, Marion
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p. 2917 - 2930
(2007/10/03)
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- 1-arylsulfonyl-3-(α-hydroxybenzyl)-1H-pyrroles, a novel class of anti-HIV-1 reverse transcriptase inhibitors
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Various 1-arylsulfonyl-3-(α-hydroxybenzyl)-1H-pyrroles were prepared by Friedel-Crafts reaction of 1-arylsulfonyl-1H-pyrroles with aroylchlorides in the presence of aluminum trichloride, followed by reduction of the ketones to the required carbinols. The compounds were identified as a novel class of non-nucleoside HIV-1 reverse transcriptase inhibitors characterized by the presence of a diarylcarbinol moiety, a chemical feature that strictly correlates with the anti-HIV-1 activity.
- Artico, Marino,Di Santo, Roberto,Costi, Roberta,Massa, Silvio,Scintu, Franca,Loi, Anna Giulia,De Montis, Antonella,La Colla, Paolo
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p. 1931 - 1936
(2007/10/03)
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- Synthesis and polymerization of 2-(3-pyrrolyl)acetic acid derivatives from pyrrole
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The synthesis of the 3-pyrrylacetic acid as well as the study of its esterification conditions are described. The new materials thus obtained are electropolymerized.
- Ho-Hoang, Ahn,Fache, Fabienne,Lemaire, Marc
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p. 1289 - 1304
(2007/10/03)
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- A facile synthesis of N-substituted pyrroles
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Phosphorous pentoxide is the catalyst of choice for the facile conversion of primary amines, aromatic amines, sulfonamides and primary amides into the corresponding N-substituted pyrroles from 2,5-dimethoxytetrahydrofuran.
- Fang,Leysen,Ottenheijm
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p. 1857 - 1861
(2007/10/02)
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- Formation and Deposition of Langmuir Films of Binary and Ternary Systems
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Long chained alkylheteroaromatic compounds such as: 3-n-alkylpyrroles, 1-n-alkylimidazoles, phenylhydrazones of 3-n-alkanoylpyrrole and poly(3-n-alkylthiophenes) with 12 to 18 carbon atoms in the alkyl chain were synthesized as materials for formation of Langmuir and Langmuir-Blodgett films by both individual species as well as by mixtures. It was shown that a positive synergy exists in binary and ternary mixtures containing poly(3-n-alkylthiophenes) resulting in formation of good-quality film on aqueous surface. Several compounds were found to be good films builders for poly(3-n-alkylthiophenes) facilitating the film transfer onto solid surfaces. Among the species examined the best builder was 3-n-octadecylpyrrole. Key words: Langmuir-Blodgett films, poly(3-n-alkylthiophenes), alkylpyrroles, alkylimidazoles, synthesis
- Kucharski, S.,Janik, R.,Bryjak, M.,Bienkowski, M.,Chyla, A.,Sworakowski, J.
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p. 447 - 460
(2007/10/02)
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- N-p-Toluenesulfonylpyrroles from 1,3-dienes
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1,3-Dienes can be converted to N-p-toluenesulfonylpyrroles in two steps: 1) [4+2]-cycloaddition with N-sulfinyl-p-toluenesulfonamide and 2) conversion of the 3,6-dihydro-1,2-thiazine oxide adduct to a pyrrole using triethylamine-trimethylphosphite.
- Harrington,Sanchez
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p. 175 - 180
(2007/10/02)
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- Palladium(II) Catalysed 5-endo-trigonal Cyclization of 2-Hydroxybut-3-enylamines: Synthesis of Five-membered Nitrogen Heterocycles
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2-Hydroxybut-3-enylamines 1 undergo a novel PdII-catalysed 5-endo-trigonal cyclization to provide pyrrolines 2, pyrroles 3, and/or 3-oxopyrrolidines 4 in good to moderate combined isolated yields; the hydroxy group is essential for the cyclizat
- Kimura, Masanari,Harayama, Hiroto,Tanaka, Shuji,Tamaru, Yoshinao
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p. 2531 - 2534
(2007/10/02)
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