- IBX-Promoted Oxidative Cyclization of N-Hydroxyalkyl Enamines: A Metal-Free Approach toward 2,3-Disubstituted Pyrroles and Pyridines
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An iodoxybenzoic acid-mediated selected oxidative cyclization of N-hydroxyalkyl enamines was developed. Through this strategy, a variety of 2,3-disubstituted pyrroles and pyridines were produced in good selectivity involving oxidation of alcohol, followed by condensation of aldehyde and α-C of enamines. Furthermore, this metal-free method has several advantages, including the use of environmentally friendly reagents, broad substrate scope, mild reaction conditions, and high efficiency.
- Gao, Peng,Chen, Huai-Juan,Bai, Zi-Jing,Zhao, Mi-Na,Yang, Desuo,Wang, Juan,Wang, Ning,Du, Lele,Guan, Zheng-Hui
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p. 7939 - 7951
(2020/07/16)
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- 2-aryl-3-ester-group polysubstituted pyrrole compound and synthesis and refining method thereof
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The invention belongs to the field of chemical synthesis, and relates to a series of 2-aryl-3-ester-group polysubstituted pyrrole compounds and a synthesis and refining method thereof. A general formula of the compounds is shown as a formula (I), wherein
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Paragraph 0116; 0117; 0118
(2019/01/08)
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- One-Pot Synthesis of 3-Substituted 2-Arylpyrrole in Aqueous Media via Addition-Annulation of Arylboronic Acid and Substituted Aliphatic Nitriles
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Pd(II)-catalyzed C-C coupling reactions between substituted aliphatic nitriles and arylboronic acids followed by in situ cyclodehydration have been employed for the first time to synthesize a wide variety of 3-substituted 2-aryl-1H-pyrroles in aqueous acetic acid. This one-pot synthesis is green, and it conforms to atom economy. The structures of two representative pyrroles, 3k and 5f, were confirmed by X-ray crystallographic analysis.
- Yousuf, Md,Adhikari, Susanta
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p. 2214 - 2217
(2017/05/12)
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- The synthesis of pyrroles and oxazoles based on gold α-imino carbene complexes
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Cationic gold complexes of α-oximimino carbenes have been identified to react with weak nucleophiles including enol ethers and nitriles. These findings allowed us to develop the highly efficient synthesis of pyrroles and oxazoles.
- Loy, Nicole S. Y.,Choi, Subin,Kim, Sunggak,Park, Cheol-Min
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p. 7336 - 7339
(2016/06/14)
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- SUBSTITUTED PYRROLES ACTIVE AS KINASES INHIBITORS
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The present invention relates to substituted pyrrole compounds which modulate the activity of protein kinases and are therefore useful in treating diseases caused by dysregulated protein kinase activity, in particular Jak family kinases. The present invention also provides methods for preparing these compounds, pharmaceutical compositions comprising these compounds, and methods of treating diseases utilizing such compounds or the pharmaceutical compositions containing them.
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Page/Page column 32
(2014/02/16)
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- Regioselective synthesis of functionalized pyrroles via gold(I)-catalyzed [3+2] cycloaddition of stabilized vinyl diazo derivatives and nitriles
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The reaction of nitriles with alkenyldiazo compounds in the presence of gold catalysts provides functionalized pyrrole derivatives in moderate to high yields. This formal [3+2] cyclization reaction takes place with complete regioselectivity. The observed regiochemical outcome suggests the attack of the nitrile to the terminal position of the alkenylgold carbenoid (vinylogous reactivity). A broad range of nitriles (including those bearing functional groups) is compatible with this cyclization reaction. Copyright
- Lonzi, Giacomo,Lopez, Luis A.
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supporting information
p. 1948 - 1954
(2013/08/23)
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- Silver-catalyzed isocyanide-alkyne cycloaddition: A general and practical method to oligosubstituted pyrroles
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Ag2CO3 is the key: The transition-metal-catalyzed cycloaddition of isocyanides and unactivated terminal alkynes has been realized with Ag2CO3 as a unique and robust catalyst (see scheme). The protocol is highly
- Liu, Jianquan,Fang, Zhongxue,Zhang, Qian,Liu, Qun,Bi, Xihe
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supporting information
p. 6953 - 6957
(2013/07/25)
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- A new pyrrole synthesis via silver(I)-catalyzed cycloaddition of vinylogous diazoester and nitrile
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A new synthesis of di- and trisubstituted pyrroles was achieved by treating in situ generated vinylogous diazoesters and readily available nitriles with a catalytic amount of silver(I) antimony hexafluoride at room temperature. This method showcased the potential of utilizing silver(I) carbenoids in preparing heterocyclic compounds.
- Billedeau, Roland J.,Klein, Klara R.,Kaplan, Daniel,Lou, Yan
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p. 1421 - 1423
(2013/06/26)
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- Synthesis of γ-azido-β-ureido ketones and their transformation into functionalized pyrrolines and pyrroles via staudinger/aza-wittig reaction
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A simple two-step procedure yielding γ-azido-β-ureido ketones or/and their cyclic isomers, 6-(1-azidoalkyl)-4-hydroxyhexahydropyrimidin-2- ones, has been developed. The synthesis includes three-component condensation of acetals of 2-azidoaldehydes with urea or methylurea and p-toluenesulfinic acid in aqueous formic acid followed by reaction of the obtained N-[(2-azido-1-tosyl) alkyl]ureas with sodium enolates of α-functionalized ketones. The azido ketones or their cyclic isomers are transformed into ureido-substituted Δ1- or/and Δ2-pyrrolines via Staudinger/aza-Wittig reaction promoted by PPh3. The obtained pyrrolines are converted into 3-functionalized 1H-pyrroles via elimination of urea under acidic conditions. Convenient one-pot syntheses of 1H-pyrroles starting from N-[(2-azido-1-tosyl)alkyl]ureas or γ-azido-β-ureido ketones have been also developed.
- Fesenko, Anastasia A.,Shutalev, Anatoly D.
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p. 1190 - 1207
(2013/04/10)
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- Copper-mediated aerobic synthesis of 3-azabicyclo[3.1.0]hex-2-enes and 4-carbonylpyrroles from N-allyl/propargyl enamine carboxylates
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Synthetic methods for 3-azabicyclo[3.1.0]hex-2-enes and 4-carbonylpyrroles have been developed that use copper-mediated/catalyzed reactions of N-allyl/propargyl enamine carboxylates under an O2 atmosphere and involve intramolecular cyclopropanation and carbooxygenation, respectively. These methodologies take advantage of orthogonal modes of chemical reactivity of readily available N-allyl/propargyl enamine carboxylates; the complementary pathways can be accessed by slight modification of the reaction conditions.
- Toh, Kah Kah,Wang, Yi-Feng,Ng, Eileen Pei Jian,Chiba, Shunsuke
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supporting information; experimental part
p. 13942 - 13945
(2011/10/30)
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- 3-AMINO-2-PHENYLPYRROLIDINE DERIVATIVES
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3-amino-2-phenylpyrrolidine compounds useful as NK-1 antagonists, with pharmaceutical compositions and methods of treatment comprising same, are disclosed.
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Page/Page column 39
(2010/02/14)
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- A Powerful New Strategy for Diversity-Oriented Synthesis of Pyrroles from Donor-Acceptor Cyclopropanes and Nitriles
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(Equation presented) Lewis acid activated donor-acceptor cyclopropanes react with aliphatic, aromatic, and α,β-unsaturated nitriles in a novel cascade [3 + 2] dipolar cycloaddition, dehydration, and tautomerization sequence to afford pyrroles in moderate
- Yu, Ming,Pagenkopf, Brian L.
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p. 5099 - 5101
(2007/10/03)
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- Unsaturated Sulfoxides in Organic Synthesis: a New General Pyrrole Synthesis
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Pyrroles have been efficiently synthesised by a three-step reaction sequence.Michael addition of keto esters onto phenyl vinyl sulfoxide followed by Pummerer rearrangement gave the cyclic key intermediate 3.Mercury(II) salt induced carbon-sulfur bond clea
- Chan, Wing Hong,Lee, Albert W. M.,Lee, Ka Ming,Lee, Tin Yau
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p. 2355 - 2356
(2007/10/02)
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- Reaction of Acyclic Imides with 1-Ethoxycarbonylcyclopropyltriphenylphosphonium Tetrafluoroborate: An Easy Route to 1H-Pyrrole-3-carboxylates
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The reaction of anions of the acyclic imides 1 with the cyclopropylphosphonium salt 2 yields ethyl 1-acyl-Δ2-pyrroline-3-carboxylates 3, substituted in position 2, which can be dehydrogenated to yield the corresponding 1-acylpyrroles 4 and subsequently deacylated to give the pyrroles 5.The scope of the reaction is discussed.
- Flitsch, Wilhelm,Pandl, Klaus,Russkamp, Petra
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p. 529 - 534
(2007/10/02)
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- Reactivite des N-vinylaziridines fonctionalisees. Synthese de derives des α,β-dehydro α-amino acides
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Secondary 2-cyano- and 2-ethoxycarbonylaziridines react with acetylenic compounds and activated vinylic chlorides to gives 2-cyano and 2-ethoxycarbonyl N-vinylaziridines.The nucleophile-catalysed isomerization of these compounds generally gives α,β-dehydr
- Gelas-Mialhe, Yvonne,Touraud, Evelyne,Vessiere, Roger
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p. 2830 - 2851
(2007/10/02)
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