Aromatic Biheterocycles: Syntheses, Structures, and Properties

Steel, Peter J.

doi:10.1016/s0065-2725(08)60070-7

Cited by 40 publications

(7 citation statements)

References 984 publications

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“…Bi‐ and oligo‐ (hetero)aryl indoles are important building blocks in synthetic and medicinal chemistry . They are usually accessed by means of a multi‐step ring‐forming processes .…”

Section: Figurementioning

confidence: 99%

Metal‐Free Oxidative Cross Coupling of Indoles with Electron‐Rich (Hetero)arenes

Caramenti

Nandi

Waser

2018

Chemistry A European J

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A new method for the synthesis of bi-heteroaryls is reported, based on the umpolung of indoles with benziodoxol(on)e hypervalent iodine reagents (IndoleBX). The oxidative coupling of IndoleBX with an equimolar amount of electron-rich benzenes, indoles, pyrroles, and thiophenes proceeded under mild transition-metal-free conditions. Functionalized non-symmetrical bi-indolyl heterocycles were accessed efficiently. Introduction of a new type of C2-substituted indole benziodoxole reagents further allowed extending the scope of the reaction to NH unprotected and C3-alkylated indoles. The obtained bi-heterocycles are important building blocks in synthetic and medicinal chemistry, and could be easily transformed into more complex heterocyclic systems.

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Section: Figurementioning

confidence: 99%

Metal‐Free Oxidative Cross Coupling of Indoles with Electron‐Rich (Hetero)arenes

Caramenti

Nandi

Waser

2018

Chemistry A European J

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“…Carboxylic acids, especially in hydrates, form strong interactions that may strongly influence the different forms of structures, usually forming supramolecular synthons (Dziuk et al, 2014a(Dziuk et al, ,b, 2017Braga et al, 2013;Ejsmont & Zaleski, 2006). 2,2 0 -Bipyridine derivatives are classical bidentate chelating heterocyclic ligands (Steel, 1996) employed in transition metal catalysis and inorganic syntheses (e.g. aluminium-initiated polymerization; Blau, 1888;Mardare & Matyjaszewski, 1994) because of their robust redox stability and ease of functionalization (Kaes et al, 2000).…”

Section: Structure Descriptionmentioning

confidence: 99%

“…Their use as building blocks for the construction of efficient molecular and macromolecular nonlinear optical chromophores is an area of great interest (Coe et al, 2005). 2,2 0 -Bipyridine data reports has been used for more than a century as common chelating ligand in analytical, organometallic and coordination chemistry (Steel, 1996).…”

Section: Structure Descriptionmentioning

confidence: 99%

2,2′-Bipyridin-1-ium hemioxalate oxalic acid monohydrate

Dziuk

Jezuita

2018

IUCr Data

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The asymmetric unit of the title compound, C10H9N2 +·0.5C2O4 2−·C2H2O4·H2O, consists of a 2,2′-bipyridinium cation, half an oxalate dianion, one oxalic acid and one water molecule. One N atom in 2,2′-bipyridine is unprotonated, while the second is protonated and forms an N—H...O hydrogen bond. In the crystal, the anions are connected with surrounding acid molecules and water molecules by strong near-linear O—H...O hydrogen bonds. The water molecules are located between the anions and oxalic acids; their O atoms participate as donors and acceptors, respectively, in O—H...O hydrogen bonds, which form sheets arranged parallel to the ac plane.

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“…Thiadiazoles are heterocyclic organic compounds with a comprehensive range of biological activities, such as anticancer [ 6 ], antivirus [ 7 ], antimicrobial [ 8 ], and anti-inflammatory [ 9 ]. Heterocycles are used in analytical chemistry [ 10 ] and have pharmaceutical properties [ 11 ]. Thiadiazoles are described and quantum chemistry is used to elucidate the chemical reactions in [ 12 ].…”

Section: Introductionmentioning

confidence: 99%

New Route Synthesis of Thiadiazoles, Bisthiadiazoles, Thiadiazolotriazines, and Pyrazolothiadiazoles Based on Hydrazonoyl Halides and Dihydrazinylthiadiazole

Sayed

Al‐Shihry

2017

Molecules

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Synthesis and characterization of new thiadiazoles, bisthiadiazoles from the reaction of mono- and di-hydrazonoyl halides with various hydrazinecarbodithioate derivatives were studied. Treatment of hydrazonoyl halides with 2,5-dihydrazinyl-1,3,4-thiadiazole afforded new bistriazines containing thiadiazole; we also examined the reaction of 2,5-dihydrazinyl-1,3,4-thiadiazole with active methylene compounds to afford new pyrazoles containing thiadiazole compounds. The new synthesized compounds were identified by elemental analysis and various spectral data (Fourier transform infrared spectroscopy, mass spectrometry, 1H and 13C nuclear magnetic resonance).

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Aromatic Biheterocycles: Syntheses, Structures, and Properties

Cited by 40 publications

References 984 publications

Metal‐Free Oxidative Cross Coupling of Indoles with Electron‐Rich (Hetero)arenes

Metal‐Free Oxidative Cross Coupling of Indoles with Electron‐Rich (Hetero)arenes

2,2′-Bipyridin-1-ium hemioxalate oxalic acid monohydrate

New Route Synthesis of Thiadiazoles, Bisthiadiazoles, Thiadiazolotriazines, and Pyrazolothiadiazoles Based on Hydrazonoyl Halides and Dihydrazinylthiadiazole

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