cas 7126-39-8, Pyrrole-3-carboxaldehyde | Articles data

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Synthesis of H-bonding probes of α7 nAChR agonist selectivity
The α7 subtype of the nicotinic acetylcholine receptor (nAChR) is the target of studies aimed at identifying features that will lead to the development of selective therapeutics. Five arylidine anabaseines, three with pyridine rings and two with the pyrrole rings, were synthesized in 35-65% yield via aldol condensation. The compounds are homologs of benzylidine anabaseine and were chosen for synthesis because they provide either a hydrogen bond acceptor (pyridines) or hydrogen bond donor (pyrroles) that may interact with the receptor within the benzylidine selectivity motif. Initial analysis of the new compounds at 100 μM concentration reveal that the two pyrrole anabaseines are good partial agonists of the α7 nAChR, having 40% of the efficacy of ACh, efficacy comparable to 4OH-GTS-21, and dramatically enhanced efficacy relative to the 2- and 4-pyridinyl compounds. The pyrrole compounds were confirmed to be α7 selective, displaying preference for this receptor over muscle and heteromeric neuronal receptor subtypes.
Wang, Jingyi,Papke, Roger L.,Horenstein, Nicole A.
p. 474 - 476
(2009)
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Redox-Neutral and Atom-Economic Route to β-Carbolines via Gold-Catalyzed [4 + 2] Cycloaddition of Indolylynamides and Cyanamides
Gold(I)-catalyzed [4 + 2] cycloaddition of indolylynamides and cyanamides (aminonitriles) is an efficient redox-neutral and atom-economic route to diversely substituted 1,3-diamino-β-carbolines. The protocol operates under mild conditions (Ph3PAuNTf2 5 mol %, DCE, 60 °C) with a good tolerance to functional groups (23 examples and yields up to 98%). The obtained β-carboline systems represent a versatile synthetic platform with modifiable substituents for successive functionalizations. Control experiments indicate the crucial role of both the nature of reactants and the identity of employed catalysts in the developed cycloaddition.
Chikunova, Elena I.,Dar’in, Dmitry,Dubovtsev, Alexey Yu.,Kukushkin, Vadim Yu.,Shcherbakov, Nikolay V.
p. 17804 - 17815
(2021/12/06)

4-Acyl Pyrrole Capped HDAC Inhibitors: A New Scaffold for Hybrid Inhibitors of BET Proteins and Histone Deacetylases as Antileukemia Drug Leads
Multitarget drugs are an emerging alternative to combination therapies. In three iterative cycles of design, synthesis, and biological evaluation, we developed a novel type of potent hybrid inhibitors of bromodomain, and extra-terminal (BET) proteins and histone deacetylases (HDACs) based on the BET inhibitor XD14 and well-established HDAC inhibitors. The most promising new hybrids, 49 and 61, displayed submicromolar inhibitory activity against HDAC1-3 and 6, and BRD4(1), and possess potent antileukemia activity. 49 induced apoptosis more effectively than the combination of ricolinostat and birabresib (1:1). The most balanced dual inhibitor, 61, induced significantly more apoptosis than the related control compounds 62 (no BRD4(1) affinity) and 63 (no HDAC inhibition) as well as the 1:1 combination of both. Additionally, 61 was well tolerated in an in vivo zebrafish toxicity model. Overall, our data suggest an advantage of dual HDAC/BET inhibitors over the combination of two single targeted compounds.
Ahlert, Heinz,Bhatia, Sanil,Borkhardt, Arndt,Breit, Bernhard,Gunther, Stefan,Hansen, Finn K.,Hugle, Martin,Kraft, Fabian B.,Mishra, Pankaj,Schaker-Hubner, Linda,Schliehe-Diecks, Julian,Scholer, Andrea,Warstat, Robin
p. 14620 - 14646
(2021/10/20)

Synthesis of aminal-type Lilium candidum alkaloids and lilaline; determination of their relative configuration by the concerted use of NMR spectroscopy and DFT conformational analysis
We hereby report the synthesis of six racemic alkaloids isolated from Lilium candidum L. Their common structural feature is a five-membered lactam ring which is, in the case of the flavonoid alkaloid lilaline, attached to the molecule's aromatic core, while in the case of the other five compounds, it is connected to the nitrogen atom of a pyrrolinone ring by an aminal function. The syntheses of these natural products were achieved via Mannich-type alkylations through cyclic N-acyliminium ions as intermediates. Besides the synthesis, the so far unexplored stereochemistry of these natural products was determined by a combination of NMR-based proton–proton distance measurements and theoretical conformational analyses carried out at the DFT level.
Nagy, Sándor,Szigetvári, áron,Ilkei, Viktor,Krámos, Balázs,Béni, Zoltán,Szántay, Csaba,Hazai, László
(2021/01/25)

Polycyclic amide derivative as CDK9 inhibitor, and preparation method and application thereof
The invention belongs to the technical field of polycyclic amide derivatives, and particularly relates to a polycyclic amide derivative as a CDK9 inhibitor, and a preparation method and application thereof. The polycyclic amide derivative shows excellent CDK9 enzyme inhibitory activity, and can be used for preparing drugs for treating cancers, especially hematologic cancers including acute myeloid leukemia, multiple myeloma, chronic lymphocytic leukemia, follicular lymphoma and the like and solid tumors, such as acute myeloid leukemia, multiple myeloma, chronic lymphocytic leukemia and follicular lymphoma, including breast cancer, prostate cancer, ovarian cancer, hepatocellular carcinoma, pancreatic cancer, kidney cancer, stomach cancer, colorectal cancer, lung cancer and the like.
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Paragraph 0236-0238; 0241; 0242

(2021/07/24)

Preparation method of moxifloxacin degradation impurity J
The invention discloses a preparation method of a moxifloxacin degradation impurity J. The method comprises the following steps: carrying out a Wittig reaction, a reduction reaction and an amino protection reaction on a raw material pyrrole-3-carbaldehyde to prepare an amino-protected moxifloxacin degradation impurity J side chain, performing a substitution reaction on the amino-protected moxifloxacin degradation impurity J side chain and 1-cyclopropyl-6,7-difluoro-8-methoxy-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid to prepare an amino-protected moxifloxacin degradation impurity J, and removing the protective group to finally prepare the moxifloxacin degradation impurity J. The impurity J product obtained by the method has a high purity and a high yield.
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Paragraph 0043-0045

(2020/01/12)

Application of 2-aryl substituted pyrrole compound in medicine for killing oncomelania hupensis
The invention relates to an application of 2-aryl substituted pyrrole compound in a medicine for killing oncomelania hupensis and belongs to the technical field of prevention and treatment of bilharziasis, and particularly provides the chemical structure of the 2-aryl substituted pyrrole compound and a preparation method of same. The 2-aryl substituted pyrrole compound, being an active component,is used for preparing the snail killing agent in the forms of suspending agents, emulsions and micro-emulsions for killing the oncomelania hupensis. Immersion killing use amount of the 2-aryl substituted pyrrole compound being the active component of the snail killing agent is 0.1-10.00 mg/l, and immersion killing time is 24-72 h. The use amount of spray application is 1-10 g/m and action timeis 3-7 days. Experiment proves that the 2-aryl substituted pyrrole compound has killing activity on the oncomelania hupensis and is lower than a snail killing agent, niclosamide, in the prior art in toxicity on aquatic organisms. The compound can be processed to prepare the snail killing agents and applied in the field of prevention and treatment of bilharziasis.
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Paragraph 0060; 0062; 0065; 0066; 0067

(2019/01/08)

Application of 2-aryl substituted pyrrole compound in medicine for killing biomphalarid snails
The invention relates to an application of 2-aryl substituted pyrrole compound in a medicine for killing biomphalarid snails and belongs to the technical field of prevention and treatment of bilharziasis, and particularly provides the chemical structure of the 2-aryl substituted pyrrole compound and a preparation method of same. The 2-aryl substituted pyrrole compound, being an active component, is used for preparing the snail killing agent in the forms of suspending agents, emulsions and micro-emulsions for killing the biomphalarid snail. Immersion killing use amount of the 2-aryl substitutedpyrrole compound being the active component of the snail killing agent is 0.5-10.00 mg/l, and immersion killing time is 24-72 h. Experiment proves that the 2-aryl substituted pyrrole compound has killing activity on the biomphalarid snails and is lower than a snail killing agent, niclosamide, in the prior art in toxicity on aquatic organisms. The compound can be processed to prepare the snail killing agents and applied in the field of prevention and treatment of bilharziasis.
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Paragraph 0068; 0070; 0073; 0074; 0075

(2019/01/08)

Intramolecular Didehydro-Diels-Alder Reaction for the Synthesis of Benzo- and Dihydrobenzo-Fused Heterocycles
Using an intramolecular didehydro-Diels-Alder reaction, ene-yne substituted pyrroles, thiophenes, and furans afford functionalized indoles, benzothiophenes, and benzofurans and the corresponding dihydroaromatic products. Product selectivity for the aromatic or dihydroaromatic product is controlled by the reaction conditions, which vary depending upon the substrate.
Bober, Ashley E.,Proto, Justin T.,Brummond, Kay M.
supporting information
p. 1500 - 1503
(2017/04/13)

Platinum-catalyzed domino reaction with benziodoxole reagents for accessing benzene-alkynylated Indoles
Indoles are omnipresent in natural products, bioactive molecules, and organic materials. Consequently, their synthesis or functionalization are important fields of research in organic chemistry. Most works focus on installation or modification of the pyrrole ring. To access benzene-ring-functionalized indoles with an unsubstituted pyrrole ring remains more challenging. Reported herein is a platinum-catalyzed cyclization/alkynylation domino process to selectively obtain C5- or C6-functionalized indoles starting from easily available pyrroles. The work combines, for the first time, a platinum catalyst with ethynylbenziodoxole hypervalent iodine reagents in a domino process for the synthesis of polyfunctionalized arene rings and gives access to important building blocks for the synthesis of bioactive compounds and organic materials.
Li, Yifan,Waser, Jerome
supporting information
p. 5438 - 5442
(2015/04/27)

Identification of N-acylhydrazone derivatives as novel lactate dehydrogenase A inhibitors
Abstract Glycolysis is drastically increased in tumors and it is the main route to energy production with a minor use of oxidative phosphorylation. Among the key enzymes in the glycolytic process, LDH is emerging as one of the most interesting targets for the development of new inhibitors. In this context, in the present work, we carried out a virtual screening procedure followed by chemical modifications of the identified structures according to a "hit-to-lead" process. The effects of the new molecules were preliminary probed against purified human LDH-A. The compounds active at low micromolar level were additionally characterized for their activity on some cellular metabolic processes by using Raji human cell line. Within the series, 1 was considered the best candidate, and a more detailed characterization of its biological properties was performed. In Raji cells exposed to compound 1 we evidenced the occurrence of effects usually observed in cancer cells after LDH-A inhibition: reduced lactate production and NAD/NADH ratio, apoptosis. The flow cytometry analysis of treated cells also showed cell cycle changes compatible with effects exerted at the glycolytic level. Finally, in agreement with the data obtained with other inhibitors or by silencing LDH-A expression, compound 1 was found to increase Raji cells response to some commonly used chemotherapeutic agents. Taken together, all these finding are in support of the LDH-A inhibiting activity of compound 1.
Rupiani, Sebastiano,Buonfiglio, Rosa,Manerba, Marcella,Di Ianni, Lorenza,Vettraino, Marina,Giacomini, Elisa,Masetti, Matteo,Falchi, Federico,Di Stefano, Giuseppina,Roberti, Marinella,Recanatini, Maurizio
p. 63 - 70
(2015/06/30)

A Practical route to substituted 7-aminoindoles from pyrrole-3-carboxaldehydes
Among privileged structures, indoles occupy a central place in medicinal chemistry and alkaloid research. Here we report a flexible and efficient conversion of pyrrole-3-carboxaldehydes to substituted 7-amino-5-cyanoindoles. Phosphine addition to fumaronitrile proceeds with prototropic rearrangement of the initially formed zwitterion to the thermodynamically favored phosphonium ylide, which is poised for in situ Wittig olefination. The predominantly E-alkene product positions the allylic nitrile for facile intramolecular Hoeben-Hoesch reaction in the presence of BF3·OEt2. Syntheses of 2,5- and 3,5-disubstituted 7-aminoindoles are illustrated. Additionally, dianion alkylation of the allylic nitrile is demonstrated to furnish, after cyclization, 5,6-disubstituted 7-aminoindoles to further exemplify this scalable and high-yielding method.
Outlaw, Victor K.,Townsend, Craig A.
supporting information
p. 6334 - 6337
(2015/02/19)

METHODS OF MODULATING CFTR ACTIVITY
The invention encompasses methods of modulating CFTR activity in a subject in need thereof comprising administering an effective amount of a compound of Formula (I). The invention also encompasses methods of treating a condition associated with CFTR activity or condition associated with a dysfunction of proteostasis comprising administering to a subject an effective amount of a compound of Formula (I).
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Page/Page column 90

(2015/01/16)

Discovery of a novel pyrrole derivative 1-[5-(2-fluorophenyl)-1-(pyridin-3- ylsulfonyl)-1 H -pyrrol-3-yl]- n -methylmethanamine fumarate (tak-438) as a Potassium-Competitive Acid Blocker (P-CAB)
In our pursuit of developing a novel and potent potassium-competitive acid blocker (P-CAB), we synthesized pyrrole derivatives focusing on compounds with low log"‰D and high ligand-lipophilicity efficiency (LLE) values. Among the compounds synthesized, the compound 13e exhibited potent H +,K+-ATPase inhibitory activity and potent gastric acid secretion inhibitory action in vivo. Its maximum efficacy was more potent and its duration of action was much longer than those of proton pump inhibitors (PPIs). Therefore, compound 13e (1-[5-(2-fluorophenyl)-1-(pyridin-3-ylsulfonyl)- 1H-pyrrol-3-yl]-N-methylmethanamine fumarate, TAK-438) was selected as a drug candidate for the treatment of gastroesophageal reflux disease (GERD), peptic ulcer, and other acid-related diseases.
Arikawa, Yasuyoshi,Nishida, Haruyuki,Kurasawa, Osamu,Hasuoka, Atsushi,Hirase, Keizo,Inatomi, Nobuhiro,Hori, Yasunobu,Matsukawa, Jun,Imanishi, Akio,Kondo, Mitsuyo,Tarui, Naoki,Hamada, Teruki,Takagi, Terufumi,Takeuchi, Toshiyuki,Kajino, Masahiro
experimental part
p. 4446 - 4456
(2012/07/28)

A new synthetic route to 3-polyfluoroalkyl-containing pyrroles
A novel approach to 3-polyfluoroalkyl pyrroles is reported based on step by step reactions: 1,2-addition of Me3SiCN to β-alkoxyvinyl polyfluoroalkyl ketones, reduction with LiAlH4 and subsequent hydrolysis with intramolecular cyclization. The hydrolytic instability of various polyfluoroalkyl groups at position 3 of the pyrrole ring was evident and a pathway for the hydrolysis was proposed.
Shaitanova, Elena N.,Gerus, Igor I.,Kukhar, Valery P.
p. 1184 - 1187
(2008/09/18)

Acid secretion inhibitor
The present invention provides a compound having a superior acid secretion inhibitory effect and showing an antiulcer activity and the like. The present invention provides a compound represented by the formula (I) wherein R1 is a nitrogen-containing monocyclic heterocyclic group optionally condensed with a benzene ring or a heterocycle, the nitrogen-containing monocyclic heterocyclic group optionally condensed with a benzene ring or a heterocycle optionally has substituent(s), R2 is an optionally substituted C6-14 aryl group, an optionally substituted thienyl group or an optionally substituted pyridyl group, R3 and R4 are each a hydrogen atom, or one of R3 and R4 is a hydrogen atom and the other is an optionally substituted lower alkyl group, an acyl group, a halogen atom, a cyano group or a nitro group, and R5 is an alkyl group or a salt thereof.
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Page/Page column 37

(2008/06/13)

NOVEL SULPHONYLPYRROLES AS INHIBITORS OF HDAC S NOVEL SULPHONYLPYRROLES
Compounds of a certain formula (I), in which R1, R2, R3, R4, R5, R6 and R7 have the meanings indicated in the description, as well as salts thereof are novel effective HDAC inhibitors.
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Page/Page column 78-79

(2008/06/13)

SULPHONYLPYRROLE HYDROCHLORIDE SALTS AS HISTONE DEACETYLASES INHIBITORS
Compounds of formula I, in which R1, R2, R3, R4, R5, R6 and R7 have the meanings indicated in the description, as well as salts thereof are novel effective HDAC inhibitors. In more detail, this invention refers to salts of a compound selected from (E)-(E)-N-hydroxy-3-(1-[4-(([2-(1H-indol-2yl)-ethyl]-methyl-amino)-methyl)-benzene sulfonyl]-1H-pyrrol-3-yl)-acrylamide, (E)-3-[1-(4-dimetylaminomethyl-benzenesulfonyl)-1H-pyrrol-3-yl]-N-hydroxy-acrylamide, and (E)-N-hydroxy-3-[1-(5-pyridin-2-yl-thiophene-2-sulfonyl)-1H-pyrrol-3-yl]-acrylamide with hydrochloric acid, their hydrates and to crystalline forms of these salts and hydrates.
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Page/Page column 62-63

(2008/06/13)

N-SULPHONYLPYRROLES AND THEIR USE AS HISTONE DEACETYLASE INHIBITORS
Compounds of a certain formula (I), in which R1 , R2, R3, R4, R5, R6 and R7 have the meanings indicated in the description, are novel effective HDAC inhibitors.
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Page/Page column 140-141

(2008/06/13)

SULFONYLPYRROLES AS HISTONE DEACETYLASE INHIBITORS
The invention thus relates to compounds of formula (I) which are effective inhibitors of histone deacetylases.
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Page/Page column 35

(2008/06/13)

Asymmetric biocatalytic hydrocyanation of pyrrole carboxaldehydes
The asymmetric hydrocyanation of pyrrole-2- and -3-carboxaldehydes substituted with either methyl, benzyl or phenyl in the 1-position catalyzed by the hydroxynitrile lyases from Hevea brasiliensis (HbHNL) and Prunus amygdalus (PaHNL) is reported. The products could be isolated - after O-silylation - with moderate to good enantiomeric purity although the carbonyl activity of the substrates was found to be very low, which is supported by quantum-chemical calculations. Structural effects concerning substrate size and regiochemistry are discussed considering docking calculations based on the X-ray crystal structures of the two enzymes. From these calculations one particular amino acid residue (Trp-128) in the active site of HbHNL could be identified, which plays a major role for the appropriate binding of structurally demanding carbonyl compounds.
Purkarthofer, Thomas,Gruber, Karl,Fechter, Martin H.,Griengl, Herfried
p. 7661 - 7668
(2007/10/03)

NOVEL AMIDO-SUBSTITUTED HYDROXY-6-PHENYLPHENANTHRIDINES
Compounds of a certain formula (I), in which R1, R2, R3, R4, R5, R6 and R7 have the meanings indicated in the description, are novel effective HDAC inhibitors.
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Page/Page column 59

(2010/02/14)

Bicyclic compounds
Substituted N-substituted alkoxyphenyl compounds, compositions containing them, and methods of making and using them.
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(2008/06/13)

Diethoxymethyl protected pyrroles: Synthesis and regioselective transformations
Treatment of the acceptor-substituted pyrroles 1a-k with neat triethyl orthoformate gives access to the diethoxymethyl (DEM) protected derivatives 2a-k in high yield. Convenient and mild cleavage was achieved by subsequent treatment of the DEM-pyrroles 2a-k with trifluoroacetic acid in acetonitrile and aqueous NaOH at room temperature. DEM protection proved suitable for a variety of regioselective transformations involving directed orthometalation and iodine-magnesium exchange processes. Furthermore, electrophilic halogenations and Pd-catalyzed coupling reactions were also carried out.
Bergauer,Gmeiner
p. 2281 - 2288
(2007/10/03)

Synthesis of protected derivatives of 3-pyrrolylalanine
Protected derivatives of 3-pyrrolylalanine (3-PA) have been synthesized starting with N-tri(isopropyl)silylpyrrole. Following formylation and Boc protection, treatment with (±)-N-(benzyloxycarbonyl)-α-phosphonoglycine trimethyl ester provided a fully protected dehydro-3-pyrrolylalanine. Reduction of the double bond and removal of the methyl ester groups yielded 3-PA protected at the α- and pyrrole nitrogens. 3-PA is only transiently stable following N-deprotection.
Beecher, Jody E.,Tirrell, David A.
p. 3927 - 3930
(2007/10/03)

Vilsmeier Formylation and Glyoxylation Reactions of Nucleophilic Aromatic Compounds Using Pyrophosphoryl Chloride
Reactions of N,N-dimethylformamide and N-methylformanilide with pyrophosphoryl chloride lead to the formation of reagents that undergo reactions with a wide range of nucleophilic aromatic substrates, including indoles, pyrroles, thiophenes, furans, and methoxy-substituted carbocyclic arenes to afford, after hydrolysis of the initial products, good to excellent yields of the expected aldehydes; reactions with methyl oxamates allow the preparation of methyl arylglyoxylates. Key words: pyrophosphoryl chloride, N,N-dimethylformamide, methoxyarene, heterocyle, formylation
Downie, Ian M.,Earle, Martyn J.,Heaney, Harry,Shuhaibar, Khamis F.
p. 4015 - 4034
(2007/10/02)

N-(Triisopropylsilyl)pyrrole. A Progenitor "Par Excellence" of 3-Substituted Pyrroles
A very effective strategy has been devised for the synthesis of 3-substituted pyrroles based on the use of the triisopropylsilyl (TIPS) moiety as a sterically demanding nitrogen substituent to obstruct the attack of electrophilic reagents at the α positions. 1-(Triisopropylsilyl)pyrrole (1) undergoes highly preferential kinetic electrophilic substitution at the β position with a variety of electrophiles (Br+, I+, NO2+, RCO+, etc.) and fluoride ion induced desilylation of the products provides the corresponding 3-substituted pyrroles in good overall yields.Competitive trifluoroacetylation experiments demonstrate that substitution of TIPS-pyrrole at the α positions is decelerated by a factor of >104, vs pyrrole at the same sites, without affecting reactivity at the β positions. 1-(Triisopropylsilyl)-3-bromopyrrole (2) is readily converted into the 3-lithio compound 44 by bromine-lithium interchange with alkyllithium reagents.This previously unavailable, formal equivalent of 3-lithiopyrrole is itself an excellent source of a wide range of β-substituted pyrroles, many of which would not be directly preparable from 1.TIPS-pyrrole can be 3,4-dihalogenated and these compounds undergo sequential halogen-metal interchange trapping reactions.This process is exemplified by an efficient, three-step synthesis of the antibiotic verrucarin E (63) from the dibromo compound (5).
Bray, Brian L.,Mathies, Peter H.,Naef, Reto,Solas, Dennis R.,Tidwell, Thomas T.,et al.
p. 6317 - 6328
(2007/10/02)

Reaction of amino sugars with malondialdehyde
2-Amino-2-deoxy-D-glucose hydrochloride reacted with the sodium salts of malondialdehyde (7) and methylmalondialdehyde (8) to give 2-deoxy-2--α,β-D-glucopyranose (12) and 2-deoxy-2--α,β-D-glucopyranose (13), respectively, in good yields.Likewise, β-D-glucopyranosylamine gave 3-(β-D-glucopyranosylamino)-2-propenal (14) and 3-(β-D-glucopyranosylamino)-2-methyl-2-propenal (15). 2-Amino-2-deoxy-β-D-glucopyranose and 7 reacted at pH ca. 9 to give a mixture of 3-pyrrolecarbaldehyde (19), 5-(D-arabino-tetritol-1-yl)-3-pyrrolecarbaldehyde (21), and 5-(α,β-D-erythrofuranosyl)-3-pyrrolecarbaldehyde (20αβ).The Na salt of crude 1 is usually contaminated with 2,4-diformyl-3-(2,2-dimethoxyethyl)glutaraldehyde (9) and 2,4-diformyl-3-methylglutaraldehyde (10), so that, in its reactions with 2-amino-2-deoxy-D-glucose hydrochloride, 2-deoxy-2-3,5-diformyl-4-(2,2-dimethoxyethyl)-1,4-dihydropyridin-1-yl)-α,β-D-glucopyranose (16) and 2-deoxy-2-(3,5-diformyl-4-methyl-1,4-dihydropyridin-1-yl)-α,β-D-glucopyranose (17) were produced in addition to 12.Likewise, with β-D-glucopyranosylamine, it afforded 14 and 3,5-diformyl-1-β-D-glucopyranosyl-4-(2,2-dimethoxyethyl)-1,4-dihydropyridine (18).Compounds 16 and 17 were obtained also by the reaction of 2-amino-2-deoxy-D-glucose hydrochloride with 9 and 10, respectively.
Gomez-Sanchez, Antonio,Maya, Ines,Hermosin, Isidro
p. 167 - 180
(2007/10/02)

SYNTHESE DE PYRROLES ET D'OXAZOLES PAR PYROLYSE DE N-(HYDROXY-2' ETHYL) AMINO-3 PROPENOATE
The gas phas pyrolysis of various N-(2'-hydroxyethyl)-3-amino propenoates 1-6 and N-(2'-hydroxy-2'-phenyl ethyl)-3-amino propanoate 7-9 at 390 deg C-420 deg C leads respectively to formylpyrroles 11-16 and benzoylpyrroles 17-19 and, in some cases, to substituted oxazoles 36-39.The results are best explained by the intermediate formation of a dicarbonyl derivative followed either by an intramolecular thermal crotonisation or a six ? electrocyclization of an azomethine ylide.
Pale-Grosdemange, Catherine,Chuche, Josselin
p. 3397 - 3414
(2007/10/02)

Synthesis of 2-Alkylputrescines from 3-Alkylpyrroles
Acylation of 2-(trichloroacetyl)pyrrole gave the 4-acyl derivatives (from 4-formyl to 4-hexanoyl) in good yields.Alkaline treatment gave corresponding 4-acyl-2-pyrrolecarboxylic acids, were decarboxylated to the 3-acylpyrroles by prior conversion to the 3-acyl-2,4,5-triiodopyrroles followed by hydrogenolysis.The 3-acylpyrroles were reduced by treatment with hydrazine in alkaline medium to the 3-alkylpyrroles.The latter were ring-opened by treatment with hydroxylamine in the presence of bicarbonate to give the dioximes of the corresponding 2-alkylsuccinaldehydes, which were then reduced to the 2-alkylpurescines (1,4-diaminobutanes).Ring-opening of 2,3-dimethylpyrrole followed by reduction of the dioxime gave 1,2-dimethylputrescine; the same sequence gave 1,3-dimethylputrescine from 2,4-dimethylpyrrole, while 3,4-dimethylpyrrole did not ring-open and gave the dioxime of 3,4-dimethylmaleimide.
Garrido, Daniel O. A.,Buldain, Graciela,Ojea, Maria I.,Frydman, Benjamin
p. 403 - 407
(2007/10/02)

N-(pyrrol-1-yl)pyridinamines having memory enhancing properties
There are disclosed novel compounds of the formula STR1 where R is H, loweralkyl, halogen, cyano, loweralkanoyl, arylloweralkanoyl, aroyl, --CH(OH)r1, --C(OH)r1 r2 or --CH2 Or2, where r1 is
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(2008/06/13)

N-(pyrrol-1-yl)pyridinamines having memory enhancing activity
There are disclosed novel compounds of the formula STR1 where n is 0 or 1; R is hydrogen or loweralkyl; R1 is hydrogen, loweralkyl, halogen, cyano, loweralkanoyl, arylloweralkanoyl, aroyl, --CH(OH)R4, --C(OH)R4 R5/su
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(2008/06/13)

PYRROLE CHEMISTRY. PART XXIX. A RE-EXAMINATION OF THE DECARBOXYLATION OF 4-ACETYL-, 4-FORMYL- AND 4-CYANO-PYRROLE-2-CARBOXYLIC ACIDS
Decarboxylation of the readily available 4-acyl-2-pyrrolecarboxylic acids has been neglected owing to the poor yields reported in the literature.This study shows that high yields are possible under the correct reaction conditions.
Anderson, Hugh J.,Clase, J. Andrew,Loader, Charles E.
p. 401 - 408
(2007/10/02)

3-Lithiopyrroles by Halogen-Metal Interchange of 3-Bromo-1-(triisopropylsilyl)pyrroles. Synthesis of Verrucarin E and Other 3-Substituted Pyrroles.
3-Lithio-1-(trimethylsilyl)pyrrole (7, Scheme 2), obtained by halogen-metal interchange from the 3-bromo compound 2, reacted with various electrophilic reagents to provide products, which on fluoride ion desilylation, gave 3-substituted pyrroles in good overall yields.One such pyrrole 13 (Scheme 3), was converted into 2-formyl-3-octadecylpyrrole (14), reputed to be a metabolite of the marine sponge Oscarella lobularis. 3,4-Dibromo-1-(triisopropylsilyl)pyrrole (5) was efficiently transformed, by a process involving two conscutive bromine-lithium exchange reactions (Scheme 4), into the antibiotic verrucarin E 17.
Muchowski, Joseph M.,Naef, Reto
p. 1168 - 1172
(2007/10/02)

Acid-Mediated Rearrangement of Acylpyrroles
N-Alkyl-2-acylpyrroles are converted by strong anhydrous acid to 1-alkyl-3-acylpyrroles.An equilibrium mixture of 2- and 3-acylpyrrole is produced by treatment of a 2- or 3-acyl NH pyrrole with acid.Pyrrolecarboxaldehydes similarly afford isomeric mixtures.A cross-ring migration, 7->8, is observed when the adjacent position is blocked.The mechanism of acid-mediated rearrangement of acylpyrroles is discussed.
Carson, John R.,Davis, Nancy M.
p. 839 - 843
(2007/10/02)

Preparation of β-acyl pyrroles
A process for rearranging α-acyl pyrroles to β-acyl pyrroles which comprises reacting the former with an excess of a strong, anhydrous, non-oxidizing acid, preferably with heating.
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(2008/06/13)