With Tag: Heterocyclic Compounds (more Than One Hetero Atom)

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Asymmetric Hydrogenation of Heteroaromatic Compounds

Yong-Gui Zhou
Acc. Chem. Res. | 2007 | 10.1021/ar700094b

Asymmetric hydrogenation of heteroaromatic compounds has emerged as a promising new route to saturated or partially saturated chiral heterocyclic compounds. In this Account, we outline recent advances in asymmetric hydrogenation of heteroaromatic compounds,...


Synthesis of Fluorous and Nonfluorous Polycyclic Systems by One-Pot, Double Intramolecular 1,3-Dipolar Cycloaddition of Azomethine Ylides

Yimin Lu, Steven Geib, Wei Zhang
Org. Lett. | 2005 | 10.1021/ol0507773

Under microwave irradiation, a one-pot, double intramolecular [3 + 2]-cycloaddition reaction of azomethine ylides leads to formation of a novel hexacyclic ring system. The major diastereomer is isolated, and its stereochemistry is determined by X-ray crystal...


Nickel-Catalyzed Direct Arylation of Azoles with Aryl Bromides

Masahiro Miura, Hitoshi Hachiya, Tetsuya Satoh, Koji Hirano
Org. Lett. | 2009 | 10.1021/ol900159a

Nickel catalyst systems for the direct C2 arylation of oxazoles and thiazoles have been developed. The catalyst systems are cost-efficient and allow the use of various aryl bromides in the C−H arylation of azoles.


Isoxazole → Benzisoxazole Rearrangement Promoted Cascade Reactions Affording Stereodefined Polycycles

Hidehiro Uesuka, Keisuke Suzuki, Jeffrey W. Bode
Org. Lett. | 2003 | 10.1021/ol0272848

A new chemo-, regio-, and stereoselective cascade reaction features a novel isoxazole → benzisoxazole rearrangement and affords highly functionalized, differentially protected compounds. The products of this reaction are directly converted to a number of...


Cobalt- and Iron-Catalyzed Redox Condensation of o-Substituted Nitrobenzenes with Alkylamines: A Step- and Redox-Economical Synthesis of Diazaheterocycles

Ludmila Ermolenko, Julie Le Bescont, Ali Al-Mourabit, Thanh Binh Nguyen
Org. Lett. | 2013 | 10.1021/ol403064z

A wide variety of functionalized 2-aryl benzimidazoles can be prepared by a solvent-free cobalt- or iron-catalyzed redox condensation of 2-nitroanilines and benzylamines. The cascade including benzylamine oxidation, nitro reduction, condensation, and...


Stereoselective Synthesis of Protected 1,2-Diols and 1,2,3-Triols by a Tandem Hydroboration−Coupling Sequence

Manmohan Kapur, Martin E. Maier, Anton Khartulyari
Org. Lett. | 2006 | 10.1021/ol0602194

A new approach to complex chiral diols and polyols is described utilizing a tandem hydroboration/Suzuki cross-coupling reaction. This method utilizes the versatility of a glycolate-derived chiral template.


Cyclic Sulfamidates as Vehicles for the Synthesis of Poly- and Diversely Substituted Benzosultams via Unusual S(O)2−O Bond Cleavage

Eric Deniau, Axel Couture, Magali Lorion, Vangelis Agouridas, Pierre Grandclaudon
Org. Lett. | 2010 | 10.1021/ol100288k

1,2-Cyclic sulfamidates undergo novel, efficient, and regiospecific intramolecular nucleophilic cleavage with aryllithiated species to provide an entry to poly-, diversely, and enantiopure N-substituted benzosultams.


Palladium-Catalyzed Direct C–H Bond Alkynylations of Heteroarenes Using gem-Dichloroalkenes

Lutz Ackermann, Yingjun Zhu, Christoph Kornhaass
Org. Lett. | 2012 | 10.1021/ol300514d

Palladium-catalyzed direct alkynylations of heteroarenes were accomplished with inexpensive gem-dichloroalkenes as user-friendly electrophiles, which set the stage for a modular, step-economical synthesis of diversely decorated heteroaryl alkynes with ample...


A Modular Sydnone Cycloaddition/Suzuki−Miyaura Cross-Coupling Strategy to Unsymmetrical 3,5-Bis(hetero)aromatic Pyrazoles

Nuno Monteiro, Jean-Pierre Vors, Geneviève Balme, Pierre Genix, Mazen Es-Sayed, Thierry Delaunay
Org. Lett. | 2010 | 10.1021/ol101087j

The [3 + 2] dipolar cycloaddition of 4-halosydnones with 1-haloalkynes opens a straightforward access to 3,5-dihalopyrazoles, valuable scaffolds for the elaboration of unsymmetrically 3,5-substituted pyrazole derivatives via site-selective Pd-catalyzed...


Enantioselective Synthesis of a Dual Orexin Receptor Antagonist

Ian K. Mangion, Benjamin D. Sherry, Jingjun Yin, Fred J. Fleitz
Org. Lett. | 2012 | 10.1021/ol3014123

A concise, enantioselective synthesis of the potent dual orexin inhibitor suvorexant (1) is reported. Key features of the synthesis include a mild copper-catalyzed amination, a highly chemoselective conjugate addition, and a tandem enantioselective...


Synthesis of 3-Substituted Indazoles from Arynes and N-Tosylhydrazones

Pan Li, Richard C. Larock, Feng Shi, Jingjing Zhao, Chunrui Wu
Org. Lett. | 2011 | 10.1021/ol201086g

Readily available, stable, and inexpensive N-tosylhydrazones react with arynes under mild reaction conditions to afford 3-substituted indazoles in moderate to good yields. The reaction appears to involve a dipolar cycloaddition of in situ generated diazo...


Generation of Nitrile Oxides from Oximes Using t-BuOI and Their Cycloaddition

Satoshi Minakata, Youhei Takeda, Toshiki Nagamachi, Sota Okumura
Org. Lett. | 2011 | 10.1021/ol2010616

tert-Butyl hypoiodite (t-BuOI) was found to be a powerful reagent for the cycloaddition of oximes and alkenes/alkynes, leading to the formation of a variety of isoxazolines or isoxazoles under mild conditions.


Catalytic Generation of Cesium Acetylide by CsF: Synthesis of 1,3-Benzothiazines from Cyclic Sulfenamides

Vincent Reboul, Cédric Spitz, Patrick Metzner, Jean-François Lohier
Org. Lett. | 2009 | 10.1021/ol9009333

An efficient synthesis of enantiopure 1,3-benzothiazines has been achieved by reaction of cyclic sulfenamides and alkylpropiolate or tosylacetylene catalyzed by cesium fluoride.


Enantioselective Intramolecular Formal [2 + 4] Annulation of Acrylates and α,β-Unsaturated Imines Catalyzed by Amino Acid Derived Phosphines

Rakesh Ganguly, Yonggui Robin Chi, Zhichao Jin, Yu Du, Ruojie Yang, Bhoopendra Tiwari
Org. Lett. | 2012 | 10.1021/ol3013588

The first chiral phosphine-catalyzed activation of acrylates for intramolecular formal [2 + 4] reactions with unsaturated imines is described. The catalytic reactions afford N-heterocycles with exceptionally high diastereo- and enantioselectivities. The [2 +...


Microwave-Assisted Fluorination of 2-Acylpyrroles: Synthesis of Fluorohymenidin

Thomas Lindel, Benjamin Troegel
Org. Lett. | 2011 | 10.1021/ol2029993

Treatment of mono- and nonbrominated 2-acylpyrroles with Selectfluor under microwave conditions leads to fluorination of the pyrrole ring in the 5-position. In particular, 2-trichloroacetylated pyrrole can be fluorinated. As an example, dihydrofluorohymenidin...


Synthesis of 2-Imidazolones and 2-Iminoimidazoles

Carl J. Lovely, Heather M. Lima
Org. Lett. | 2011 | 10.1021/ol2022438

Convenient methods for the direct conversion of imidazolium salts to the corresponding 2-imidazolone or 2-imino imidazole derivatives have been developed. Treatment of the salt with commercial bleach leads to effective oxidation at C2 and the formation of the...


Practical Synthesis of 1-Aryl-6-(hydroxymethyl)-2-ketopiperazines via a 6-exo Amide−Epoxide Cyclization

Daniel D. Holsworth, Wayne L. Cody, Noel A. Powell, Jeremy J. Edmunds, Emma C. Clay, Peter G. Blazecka, Dennis M. Downing, Fred L. Ciske
Org. Lett. | 2004 | 10.1021/ol048235t

Chiral 1-aryl-6-(hydroxymethyl)-2-ketopiperazines can be prepared via an operationally simple, 6-exo epoxide ring-opening cyclization to form the ketopiperazine C6−N1 bond in high yields and with excellent enantiomeric purity.


Intramolecular Cycloaddition Reactions of Silyl Nitronate Tethered to Vinylsilyl Group:  2-Nitroalkanols as Precursors for Amino Polyols

Seiki Saito, Yoshihiro Shimizu, Teruhiko Ishikawa, Takayuki Kudoh
Org. Lett. | 2003 | 10.1021/ol035423v

A method for converting 2-nitroalkanols to precursors for stereodefined amino polyols is described. Diphenylvinylsilylation of the 2-nitroalkanols' hydroxy groups and subsequent silyl nitronate generation by using TMS-Cl and Et 3 N in CH 3 CN at 0 °C to room...


Samarium Barbier Reactions of α-Iodomethyloxazoles and Thiazoles with Aliphatic Aldehydes

Michael P. Clark, David R. Williams, Partha P. Nag, Bryan W. Stroup, Martin A. Berliner
Org. Lett. | 2005 | 10.1021/ol051345v

The reductive coupling of substituted α-iodomethyloxazoles and thiazoles with aliphatic aldehydes under Barbier conditions provides an effective method for the direct incorporation of intact heterocyclic systems.


Copper-Catalyzed Intramolecular Cyclization to N-Substituted 1,3-Dihydrobenzimidazol-2-ones

Hongbin Sun, Hong Liu, Hualiang Jiang, Zhaoguang Li
Org. Lett. | 2008 | 10.1021/ol8011106

An efficient and convenient method was developed for preparing N-substituted 1,3-dihydrobenzimidazol-2-ones from N′-substituted N-(2-halophenyl)ureas via a CuI/DBU-catalyzed cyclization in DMSO under microwave heating. High yields were obtained and a...

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