2024 December - 58 articles
The oxidative esterification of 4,4′-Biphenyldicarboxaldehyde with hexafluoroisopropanol is reported. The methodology, making a novel hexafluoroisopropyl ester uses a green, recyclable oxoammonium salt along with easily obtained sodium persulfate.
The titular compound, 6-amino-7-((4-methoxybenzyl)thio)quinazolin-4(3H)-one, was prepared from 7-fluoro-6-nitroquinazolin-4(3H)-one via a nucleophilic aromatic substitution reaction followed by a reduction of the nitro group. Characterization of the...
5-Bromo-N′-(2-oxoindolin-3-ylidene)furan-2-carbohydrazide (1) was successfully synthesized in 79.4% yield by reaction of isatin with 5-bromofuran-2-carbohydrazide in acidic conditions under reflux. The structure of synthesized compound 1 was co...
Surfactants are very important compounds that are ubiquitous in biological systems and detergents. Among them, ferrocene surfactants are a very valuable class of stimuli-responsive materials since the presence of ferrocene moiety discloses the chance...
The title compound was characterised for the first time by 13C NMR, including the determination of CH coupling constants, and its X-ray structure was determined, showing double ribbons of molecules in the crystal held together by weak CH to O=C hydro...
The title compound (1) was obtained within a project to synthesize analogs of the antiepileptic drug stiripentol. Compound 1 was synthesized by aldol addition of the lithium enolate of 4-(benzo[d][1,3]dioxol-5-yl)butan-2-one (2) to 3,3-dimethylbutan-...
The crystal structure and the improved synthesis of the title compound (1) are presented. Treatment of 5,10-disilyldibenzo[a,e]pentalenes (2a and 2b) with iodine chloride (ICl) readily provided 1 in good yields. Recrystallization from a dichlorometha...
3-N-allylrhodanine was condensed with 5-(4-methoxyphenyl)-thiophene-2-carbaldehyde in an L-proline-based deep eutectic solvent (DES) to obtain the π-conjugated heterocyclic rhodanine compound (5Z)-3-allyl-5-{[5-(4-methoxyphenyl)thiophen-2-yl]methy...
We have successfully synthesized a 2-oxa androstane derivative, 17β-hydroxy-2-oxa-5α-androstan-3-one (6), and confirmed its structure using NMR spectroscopy and mass spectrometry.
New cyclotriphosphazene derivatives featuring amide–Schiff base linkages with a hydrazine bridge and different terminal ends, such as decyl alkyl chains and hydroxy groups, were successfully synthesized and characterized. Fourier-transform infr...
Anilides of 3-oxo-4-phenylaminobutyric acid with Troc or COOEt protection at the phenylamino group undergo competing cyclization processes in neat polyphosphoric acid at 80 °C. Depending on the protecting group and the duration of the process, th...
Ferrociphenols are anticancer organometallic molecules bearing a ferrocene group linked, at least, to one para-phenol moiety via a double bond. Up to the present, their biological activity has been thought to be linked to their oxidation within cells...
A highly efficient method has been developed for preparing 2-((3R,9bS)-5,5-dioxido-2,3-dihydro-9bH-benzo[4,5]isothiazolo[3,2-b]oxazol-3-yl)-1-phenylethan-1-one. This enantioenriched title compound was obtained via an organocatalytic asymmetric [3+2]-...
New 4-(benzoxazol-2-yl)phenyl 3-((3-chloro-1,4-naphthoquinon-2-yl)amino)phenyl sulfate was synthesized via the SuFEx click reaction between fluorosulfate-containing 1,4-naphthoquinone and 2-(4-hydroxyphenyl)benzoxazole. 1,8-Diazabicyclo[5.4.0]undec-7...
A one-carbon difluorocyclopropanation/ring-expansion has been developed for the chiral synthon Cyrene, which is obtained via cellulose pyrolysis. The ring-enlargement was achieved by converting Cyrene (dihydrolevoglucosenone) into an enamine, reactin...
The wide range of application possibilities of fluorene derivatives, due to their unique physical and chemical properties, has made this class of molecules important for various disciplines. The synthesis of these compounds and the study of their pro...
The ligandless palladium-catalyzed Heck reaction of 4-ethenyl-3-methoxy-1-phenyl-1H-pyrazole and 2-([1,1′-biphenyl]-4-yl)-5-bromo-3,3-dimethyl-3H-indole gave the previously unreported 2-([1,1′-biphenyl]-4-yl)-5-[(E)-2-(3-methoxy-1-phenyl-...
The reaction of the phosphonated hydrazone (2-hydrazineylidenepropyl) diphenylphosphine oxide 1 with p-fluorophenyl-isothiocyanate yields as a major product the thiosemicarbazone Ph2P(=O)CH2{C=N-NH(C=S)-N(H)C6H4F}CH3 (2-(1-(diphenylphosphoryl)propan-...
The reactions of dialkylzinc reagents with ketones are scarcely studied. In this paper, we describe a previously unknown direct alkylation of substituted 2-acetylpyridine with diisopropyl zinc, which gave a corresponding novel alcohol with 82% yield.
Ammonium oxathioamidate (1) was synthesised by the reaction between O-ethyl-thioxamate (oxalic acid-1-amide-2-O-ethyl ester) and ammonium hydrogen carbonate in water solution. Compound 1 was fully characterised by both microanalytical (elemental anal...
In order to investigate the coordination chemistry of O-alkyl N-aryl thiocarbamate ligands, HgI2 was reacted with one equivalent of PrOC(=S)N(H)Ph L in toluene solution to afford the 1D polymeric title compound [{IHg(μ-I)}{κ1-PrOC(=S)N(H)Ph}...
We report the synthesis of the new compound 6,8-dibromo-11H-indeno[1,2-b]quinolin-11-one, which presents an important type of nitrogen-containing heterocycles and is a useful intermediate product in organic synthesis. The structure of the compound wa...
During the purification of a reported compound named 1,3-dihydrobenzo[c]thiophene, we isolated an unexpected molecule in one of the chromatography fractions by serendipity. Structural elucidation using common techniques such as 1D and 2D NMR, and mas...
The title compound, trans-11-(3,4-Dimethoxyphenyl)-2,3,8,9-tetramethoxy-6-oxo-11,12-dihydro-6H-dibenzo[c,h]chromene-12-carboxylic acid (4), was synthesized for the first time via a two-step protocol from 3,4-dimethoxyhomophthalic anhydride (1) and 3,...
Selenium compounds have garnered significant attention in the field of medicinal chemistry due to their unique biochemical properties and potential therapeutic applications for different pathologies. In this study, we report the synthesis of a new se...
A general protocol for the synthesis of 3,4-dihalogen substituted 1,8-naphthalimides is proposed, starting from available and cheap 1,8-naphthalic anhydride. The reported new compounds have only bromine or chlorine atoms as substituents, in contrast...
The title compound with a donor–π–donor (D–π–D) type triad structure was synthesized by Buchwald–Hartwig amination using 9,10-dibromoanthracene and 5H-dibenzo[b,f]azepine, and characterized by 1H, 13C{1H} NMR, HRMS...
In the context of our ongoing studies on 3-nitroimidazo[1,2-a]pyridine derivatives as potent antileishmanial compounds, we isolated a new unexpected compound from the spontaneous cycloaddition of N-[2-(8-bromo-6-chloro-3-nitroimidazo[1,2-a]pyridin-2-...
Caffeic acid phenethyl ester (CAPE) is a phenolic natural product with diverse biological activities, notably anticancer properties. However, its ester group is metabolically unstable. The amide derivative, CAPA, offers improved metabolic stability t...
This communication reports a reliable one-pot synthetic protocol for preparation on a multigram scale of 3-bromo- and 3,4-dibromo-6-nitro-1,8-naphthalic anhydride from commercially available and economical 1,8-naphthalic anhydride. The synthetic step...
We have successfully synthesized the dichloro-bis[(Z)-1-styryl-benzimidazole]-zinc(II) complex, which was fully characterized by IR, elemental analysis, and mass and NMR spectroscopy. The solid-state structure definitively shows that two benzimidazol...
Diffractic acid 1 is a secondary metabolite of depside lichens with antibacterial and insecticidal properties, and anticancer, hepatoprotective and antiviral activities. Novel diffractaic acid derivatives containing a 1,2,4-oxadiazole ring with an ar...
Dichloro-bis(1-cinnamyl-benzimidazole)-cobalt(II) was prepared in one step using a cobalt precursor CoCl2 and corresponding substituted benzimidazole. The complex was fully characterized using IR, elemental analysis, and mass- and NMR spectroscopy. I...
Tetronic acid, a five-membered heterocyclic moiety present in various natural products, has emerged as a significant building block for many pharmaceutically active compounds. In this study, a novel protocol for the synthesis of the bis-tetronic acid...
Molbank is a unique journal, bringing together one-compound-per-paper short notes on synthetic compounds and natural products [...]
Protection of the hydroxy group in monoterpenoids borneol and isoborneol with various silyl-protective groups containing a different number of phenyl groups enabled complete assignments of the 1H chemical shifts. In particular, a wider range of the p...
Drostanolone is a popular synthetic dihydrotestosterone derivative and an anabolic–androgenic agent which belongs to the steroid class. The crystal structure of a new polymorph of the esterified prodrug of drostanolone, namely drostanolone enan...
Oligo(phenylene ethynylene)s (OPEs) are π-conjugated systems with promising optical, bioactive, and electrical properties, making them valuable candidates for molecular electronics and biosensors. Controlling the arrangement and orientation of &pi...
A new allyl derivative of curcumin containing three allyl groups (1E,6E)-4-allyl-1,7-bis(4′-allyloxy-3′-methoxyphenyl)hepta-1,6-diene-3,5-dione was synthesized by the reaction of curcumin with the excess of allyl bromide in the presence o...
Fenpiverinium is an agent which, from a medical perspective, has anticholinergic and antispasmodic properties, with applications in the treatment of smooth muscle spasm. The crystal and molecular structures of two fenpiverinium-based crystals, namely...
The chiral oxazolidine moiety is an important core in asymmetric synthesis due to its ability to participate in various stereoselective chemical reactions and because it forms part of more complex and important active compounds. Therefore, in this le...
(R)-3,3,6-trimethyl-3,3a,4,5-tetrahydro-1H-cyclopenta[c]furan was obtained by the acid cyclization of the alcohol (S)-(2-methyl-5-(prop-1-en-2-yl)cyclopent-1-en-1-yl)methanol, which, in turn, is obtained from (R)-limonene. The structure of the new co...
Reduction of the four-coordinate “ate” species [(RC(NAr)2Cr(µ-Cl)2Li(THF)2] (1) (R = diisopropylamine; Ar = 2,6-diisopropylphenyl) with potassium graphite (KC8) in toluene leads to the formation of a toluene-bridged inverted-sandwic...
Advances in synthetic peptide methodologies have enabled the development of macromolecules mimicking protein properties and have found applications in various fields, particularly in immunology. Furthermore, Sequential Oligopeptide Carriers (SOCn and...
Complete assignments of the 1H NMR chemical shifts for monoterpenes, borneol, and isoborneol, and their derivatives in which the secondary hydroxy group is protected with an acetyl group or a benzoyl group, have been made in CDCl3 and C6D6. Upon the...
A new tetracyclic morpholine-fused[5,1-c]-triazole, (4aS,5S,6aR,10aR,10bR)-5-methoxy-9,9-dimethyl-4a,5,6a,7,10a,10b-hexahydro-12H-[1,3]dioxino[4′,5′:5,6]pyrano[4,3-b][1,2,3]triazolo[1,5-d][1,4]oxazine, was synthesized via a five-step sequ...
The synthesis of 4-(1H-tetrazol-5-yl)-2-(p-tolyl)quinoline 4 as a possible modification of the biphenyltetrazole substructure of losartan 1 is described. The transformation of 2-(p-tolyl)quinoline-4-carbonitrile 3 to the corresponding tetrazole 4 was...
As an extension of our study of the reactivity of derivatives of 3,3,4,4-tetraethoxybut-1-yne, attempts have been made to achieve acid-catalyzed deacetalization of the diethoxymethyl moieties in 5-diethoxymethyl-1,1,2,2-tetraethoxyundeca-3,6-diyn-5-o...
We herein report the synthesis of a 7-chloro-aminoquinoline triazine conjugate. The s-triazine library was generated by stepwise nucleophilic substitution of cyanuric chloride with butylamine. The structure of the compound was comprehensively determi...
A series of usnic acid derivatives containing a thiazole ring with an amide substituent were synthesized. The convenient method for synthesis of these compounds is a reaction of 14-bromousnic acid with N-acylthioureas. Acylation of aminothiazole does...
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