Heteroaromatics - Science topic

Sulfonamides are valuable structural building blocks, bioactives, and pharmaceuticals. While there have been great achievements in the sulfonamidation of alkyl and alkenyl carbon, the sulfonamidation of alkynyl carbon has not been studied. Herein, we report the synthesis of N-benzylated sulfonamides from alkoxy aryl alkynes and sulfonamides enabled...

The fate of thymine upon excitation by ultraviolet radiation has been the subject of intense debate. Today, it is widely believed that its ultrafast excited state gas phase decay stems from a radiationless transition from the bright ππ* state to a dark nπ* state. However, conflicting theoretical predictions have made the experimental data difficult...

There is a growing interest in deuterated derivatives in various fields, including the pharmaceutical industry. In this industry, partially hydrogenated heterocycles are also a target. Combining these two concepts, it was studied the reduction of heterocycles with simultaneous deuterium incorporation by transfer deuteration, a process of introducin...

Electroluminescent organic molecules have been proffered as the key to unlocking a new generation of light‐emitting electrochemical cells. The article describes our development of a practicable library synthesis of a class of electroluminescent materials with a bifluorene core. The approach is applicable to an array of related materials containing...

Oxindole is a nature-derived heteroaromatic nucleus with a history of preclinical uses in various conditions. In this study, oxindole derivatives, 6-chloro-3-(3-hydroxybenzylidene) indolin-2-one (3OH) and 6-chloro-3-(4-hydroxybenzylidene) indolin-2-one (4OH) were evaluated for nephroprotective and hepatoprotective effects. Paracetamol-induced nephr...

We report here the use of amidophosphine borane {(BH₃)₂(PPh)₂N(CH₂)C₆H₅} as a competent reducing agent for the hydroboration of ketones and imines under mild and catalyst‐free reaction conditions yielding the corresponding secondary alcohols and secondary amines after aqueous work. Solid amidophosphine boranes, which are easy to synthesize, and eas...

BACKGROUND The aqueous extraction of sesame oil is a traditional process that generates a large amount of melanoidins. However, little is known about the characteristics and bioactive functions of these melanoidins. RESULTS Electronic tongue, fluorescence emission spectroscopy, and Fourier transform infrared spectroscopy analyses indicated that me...

Covalent organic frameworks (COFs) offer remarkable versatility, combining ordered structures, high porosity, and tailorable functionalities in nanoscale reaction spaces. Herein, we report the synthesis of a series of isostructural, photoactive Wurster‐type COFs achieved by manipulating the chemical and electronic nature of the Wurster aromatic ami...

This article reports a detailed mechanistic and kinetic study of an unusual photoreaction leading to the (diazonia)tetrabenzonaphthacene skeleton. The photo‐triggered double intramolecular nucleophilic aromatic substitution (SNAr*) has been investigated by varying the leaving groups. Photoreaction quantum yields have been determined and mechanistic...

A strategy for the photosensitized [2+2]‐cycloaddition between styrenyl dihaloboranes and unactivated allylamines to access cyclobutylboronates with control of stereochemistry and regiochemistry is presented. The success of the reaction relies on the temporary coordination between in situ generated dihaloboranes and amines under mild reaction condi...

Triarylamines are frequently employed as electron donor functional groups in a variety of organic electronic materials. We herein report the synthesis and in‐depth characterisation of aza‐analogues of fully bridged triarylamines, consisting of 5‐, 6‐ and 7‐membered rings. The impact of nitrogen doping and π‐extension on the structural, electronic a...

The C–H arylation of 2-quinolinecarboxyamide bearing C–Br bond at the N-aryl moiety is carried out with a palladium catalyst. The reaction proceeds at the C–H bond on the pyridine ring adjacent to the amide group in the presence of 10 mol% Pd(OAc) 2 at 110 °C to afford the cyclized product in 42% yield. The yield is improved to 94% when the reactio...

2,3’‐Bisindoles with C−C linkages have attracted interest in medicinal chemistry, yet their synthesis is intricate with many steps. Notably, direct C−H/C−H cross‐coupling of non‐directed heteroaromatics remains challenging, often requiring precious metals and oxidants to enhance coupling efficiency. Herein, we present a copper‐catalyzed C−H/C−H cro...

The cytochrome P450 homolog, TxtE, efficiently catalyzes the direct and regioselective aromatic nitration of the indolyl moiety of L‐tryptophan to 4‐nitro‐L‐tryptophan, using nitric oxide (NO) and dioxygen (O2) as co‐substrates. Pathways for such direct and selective nitration of heteroaromatic motifs present platforms for engineering new nitration...

Semiconductor‐based photoelectrochemical (PEC) organic transformations usually show radical characteristics, in which the reaction selectivity is often difficult to precisely control due to the nonselectivity of radicals. Accordingly, several simple organic reactions (e.g., oxidations of alcohols, aldehydes, and other small molecules) have been wid...

Thiourea dioxide (TDO) has been demonstrated to be an efficient reagent for the transformation of aromatic, heteroaromatic, alkenyl and aliphatic aldoximes to respective nitriles in excellent yields. Furthermore, this method has been applied to the synthesis of fungicide cyazofamid from a commercial precursor using TDO as a pivotal dehydrating and...

Replacing planar aromatic rings in drug molecules with C(sp³)-rich isosteric mimetics, such as bicyclo[n.1.1]alkanes, can significantly alter their physicochemical and pharmacokinetic properties, often leading to higher clinical success rates. However, unlike a benzene ring, the structurally rigid C(sp³)-rich isosteric mimetics of heteroaromatic ri...

Heteroaromatic species are commonly found in complex gaseous mixtures, from tobacco smoke to petroleum and asphaltene combustion products. At high temperatures, C–H bond rupture produces various dehydro radical isomers. We have used the spin–flip formulation of equation-of-motion coupled cluster theory with single and double substitutions (EOM-SF-C...

Polycyclic heteroaromatics (PHAs) are a highly versatile class of functional materials, especially applicable as efficient luminophores in organic light‐emitting diodes (OLEDs). Those constructed by tethered phenyl surrounding the main group center attract extensive attention due to their excellent OLED device performance. However, the development...

Over the decades, functionalized heteroaromatic compounds and their scaffolds have drawn significant attention in synthetic organic chemistry as well as in interdisciplinary sciences due to their prevalence in natural products, hormones, vitamins, and their applications in pharmaceuticals, agrochemicals, veterinary products, dyes and pigments, bio‐...

This study explores a novel and eco-friendly synthesis of 22 derivatives of 2-aryl/heteroaryl substituted 2,3-dihydroquinazolin-4(1H)-ones, compounds with significant medicinal potential, using concentrated solar radiation (CSR) and lemon juice as a natural catalyst. Traditional methods for synthesizing these compounds often involve complex, energy...

In this study, the synthesis of pyrazolo[3,4-b]quinolinone compounds was carried out via one-pot three-component reactions. These reactions proceed as domino processes, making them easier to occur than the conventional multistep organic reactions. By employing this method, new organic molecules can be synthesized in a single step, using minimal tim...

As a continuation of our study in the field of GABAA receptor modulators, we report the design and synthesis of new pyrazolo[1,5-a]quinazoline (PQ) bearing at the 8-position an oxygen or nitrogen function. All the final compounds and some intermediates, showing the three different forms of the pyrazolo[1,5-a]quinazoline scaffold (5-oxo-4,5-dihydro,...

Multi-resonance thermally activated delayed fluorescence (MR-TADF) materials of polycyclic heteroaromatics are attractive narrowband emitters in wide-color-gamut organic light-emitting diodes (OLEDs). However, deep-blue MR-TADF emitters with CIE coordinates fulfilling the BT.2020 standard and high efficiency still remain a significant challenge. He...

A series of new heterocycles-flanked alkoxyphenanthrenes with D′-D-D′ and A-D-A architecture was synthesized for high-performance solution-processable p-channel, n-channel, and ambipolar organic field-effect transistors. The impact of electron-donating and -accepting abilities of the sulfur- and nitrogen-containing heteroaromatics on photophysical,...

An efficient I 2 ‐promoted Povarov multicomponent reaction for the synthesis of 2,2′‐biquinolines or N ‐heteroaromatic benzothiazole using 2‐methylquinoline or 2‐methylbenzo[ d ]thiazole, arylamines, and α ‐ketoesters was developed. The methyl group of methyl aza‐arenes incorporated in the Povarov reaction via an iodination/Kornblum oxidation seque...

Circularly polarized phosphorescence (CPP) is a spin-forbidden radiative process, and its underlying mechanism is not comprehensively understood, mainly due to the limited examples of efficient triplet emission from small chiral organic molecules with well-defined structures. Here we investigate a pair of chiral enantiomers, R- and S-BBTI, that fea...

Naphthylimides play a pivotal role as aromatic heterocyclic compounds, serving as the foundational structures for numerous pharmacologically significant drugs. These drugs encompass antibacterial, antifungal, anticancer, antimalarial, antiviral, anti-inflammatory, antithrombotic, and antiprotozoal agents. The planar and heteroaromatic characteristi...

A facile, clean, and green protocol for synthesizing 5-arylidene-rhodanine derivatives (3a-3m) by the Knoevenagel condensation of variously substituted aromatic/heteroaromatic aldehydes and rhodanine using CuFe2O4 NPs as an effective magnetically separable heterogeneous catalyst in water has been developed. Mild reaction conditions, eco-friendlines...

This review presents various new strategies for the functionalization of 5 and 6-membered fused heteroaromatics. These synthetic strategies enable rapid access to complex heterocyclic compounds.

A Suzuki–Miyaura cross-coupling reaction was developed on unprotected ortho-bromoanilines. This operationally simple reaction was developed for the diversification of glucocorticoid receptor modulators (GRMs), showed compatibility to various boronic esters featuring unique functionalities, and was demonstrated on a gram scale.

The design and synthesis of two-photon-responsive chromophores have recently garnered significant attention owing to their potential applications in materials and life sciences. In this study, a novel π-conjugated system, 2-dimethylaminophenyl-5-nitrophenylthiophene derivatives, featuring a thiophene unit as the π-linker between the donor (NMe 2 C...

The magnetically recoverable heterogeneous Fe2O3@cellulose@Mn nanocomposite was synthesized by a stepwise fabrication of Mn nanoparticles on cellulose-modified magnetic Fe2O3 nanocomposites, and the morphology of the nanocomposite was characterized through advanced spectroscopic techniques. This nanocomposite was investigated as a heterogeneous cat...

Trifluoromethyl (CF3) and other fluoroalkyl groups are of great significance in the fields of pharmaceutical chemistry and agricultural chemicals. Fluoroalkyl acids, especially trifluoroacetic acid (TFA) is considered the most ideal fluoroalkylation reagent due to its low cost and easy availability. However, the extremely high oxidation potential r...

This manuscript unveils the synthesis of 2H-thiazolo[4,5-d][1,2,3]triazole (ThTz), an unprecedented [5-5]-fused heteroaromatic system, and established a scalable synthetic procedure for producing large quantities of the ThTz ring bearing a sulfone group on the thiazole ring. The sulfone moiety proves to be a versatile reactive tag, facilitating div...

Mercury, a highly toxic metal and pollutant, poses a significant risk to human health and the environment. This study describes the synthesis of a new nitrogen-doped heteroaromatic hyper-crosslinked polyamine (HCPA) via the polycondensation of 2,6-diaminopyrazine and tris(4-formylphenyl)amine for the efficient removal of mercury ions from aqueous s...

3‐methyl‐4‐(hetero)arylmethylidene isoxazole‐5(4H)‐one derivatives (4a‐r) derivatives (4a‐r) were synthesized by the multi‐component reactions. The multi‐component reactions (MCRs) of hydroxylamine hydrochloride, ethyl acetoacetate and aromatic/ heteroaromatic aldehyde catalyzed by novel Glutamic acid (Glu) as a biodegradable and eco‐friendly organ...

Tetrahydroacridines arouse particular interest due to the potential possibilities of application in the medical field and protection against corrosion. Bis-tetrahydroacridines were newly synthesized by Pfitzinger condensation of 5,5′-(ethane-1,2-diyl) diindoline-2,3-dione with several cyclanones. NMR, MS, and FT-IR were used to prove their molecula...

In the quest to enhance the efficiency and durability of n–i–p perovskite solar cells (PSCs), engineering hole-transporting conjugated polymers with well-matched energy levels, exceptional film-forming properties, rapid hole transport, and superior moduli is paramount. Here, we present a novel approach involving the customization of a conjugated po...

Among azobenzene derivatives, azothiophenes represent a relatively recent family of compounds that exhibit similar characteristics as dyes and photoreactive systems. Their technological applications are extensive thanks to the additional design flexibility conferred by the heteroaromatic ring. In this study, we present a comprehensive investigation...

Photoinduced chemical reactions and the development of new materials represent a current and significant topic. We present a sustainable and eco-friendly approach to the Knoevenagel condensation reaction involving carbonyl and active methylene compounds. Our method utilizes photo-activated carbon dots (CDs) derived from 5-hydroxymethylfurfural (5HM...

Electrocatalytic hydrogenation (ECH) was explored as a mild technique (≤50 °C under atmospheric pressure) to produce valuable products from furfural, a promising biomass-derived platform chemical. In situ hydrogen equivalents made by water splitting were used to reduce the formyl group and saturate the heteroaromatic ring of furfural on an activate...

Pyrazoles are rarely found in nature but are traditionally used in the agrochemical and pharmaceutical industries, while other areas of use are also actively developing. However, they have also found numerous other applications. The search for new and efficient syntheses of these heterocycles is therefore highly relevant. The modular concept of mul...

Organic dyes hold promise as inexpensive electrochemically‐active building blocks for new renewable energy technologies such as redox‐flow batteries and dye‐sensitised solar cells, especially if they display high oxidation and/or low reduction potentials in cheap, non‐flammable solvents such as water or protic ionic liquids. Systematic computationa...

Heteroaromatic N‐oxides, renowned for their highly polar N─O bond and robust structure, exhibit significant bioactivities and have played a pivotal role in various drug development projects since the discovery of Minoxidil. Moreover, heteroaromatic N‐oxides, featuring axially chiral biaryl frameworks, are indispensable as Lewis base catalysts and l...

Amino acids are vital motifs in the domain of biochemistry, serving as the foundational unit for peptides and proteins, while also holding a crucial function in many biological processes. Due to their bifunctional character, they have been also used for combinatorial chemistry purposes, such as the preparation of DNA-encoded chemical libraries. We...

The activation and transformation of carbon monoxide (CO), a versatile C1 feedstock, continues to attract substantial attention. Traditionally, researchers have focused on the development of catalytic systems to activate CO and then quench the generated acyl intermediate with nucleophiles to complete the carbonylative transformations. Here, non-cla...

Described herein is a tandem reaction involving a copper chloride‐catalyzed cross‐coupling and an allene‐mediated cyclization of substituted ethynylimidazo[2,1‐b]thiazoles with aromatic N‐tosylhydrazones, producing naphtho[1′,2′4,5]imidazo [2,1‐b]thiazoles in very good yields. This protocol offers the advantages of one‐pot conversion from stable an...

This review focuses on optical properties of compounds in which at least one phosphonate group is directly attached to a heteroaromatic ring. Additionally, the synthesis and other applications of these compounds are addressed in this work. The influence of the phosphonate substituent on the properties of the described compounds is discussed and com...

Direct installation of key functionalities in a molecule through C−H bond activation is one of the thrust areas as well as challenging task in organic synthesis. Particularly, introduction of chlorine in a molecule imparts additional benefits for further functionalizations as well as improves the electronic behaviour such as lipophilicity and polar...

Nitrile‐aminothiol conjugation (NATC) stands out as a promising biocompatible ligation technique due to its high chemo‐selectivity. Herein we investigated the reactivity and substrate scope of NAT conjugation chemistry, thus developing a novel pH dependent orthogonal NATC as a valuable tool for chemical biology. The study of reaction kinetics eluci...

An efficient cross-coupling of aryl bromides with sodium sulfinates, using an organoboron photocatalyst with nickel, is described herein. Under the irradiation of white light, this dually catalytic system enables the synthesis of a series of sulfone compounds in moderate to good yields. A broad range of functional groups and heteroaromatic compound...

The development of highly reducing photocatalysts to functionalize arenes via the generation of reactive aryl radicals under mild and environmentally benign reaction conditions has emerged as a noteworthy approach in the realm of organic synthesis. Herein, we report a readily synthesized series of novel naphthocarbazole derivatives (NCs) as organo-...

4-Nitroquinoline-N-oxide (NQO) and 4-nitropyridine-N-oxide (NPO) are important precursors for the synthesis of substituted heterocycles while NQO is a popular model mutagen and carcinogen broadly used in cancer research; intermolecular interactions are critical for their reactions or functioning in vivo. Herein, the effects of the coordination of N...