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The sequential reaction of differently substituted 4,4,6-trimethyl-4H-pyrrolo[3,2,1-ij]-quinoline-1,2-diones with thiosemicarbazide and dimethyl acetylenedicarboxylate yielded a series of new 2-{2-[2-(4,4,6-trimethyl-2-oxo-4H-pyrrolo[3,2,1-ij]quinolin-1(2H)-ylidene)hydrazineyl]-4-oxothiazol-5(4H)-ylidene}acetates, 2-{[(1-{2-[5-(2-methoxy-2-oxoethylidene)-4-oxo-4,5-dihydrothiazol-2-yl]hydrazineylidene}-4,4-dimethyl-2-oxo-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-6-yl)methyl]thio}benzoic acids, and 2-{[(1-{2-[5-(2-methoxy-2-oxoethylidene)-4-oxo-4,5-dihydrothiazol-2-yl]hydrazineyl-idene}-4,4-dimethyl-2-oxo-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-6-yl)methyl]thio}-nicotinic acids. The synthesized compounds were isolated as single isomers having presumably the Z,Z configuration. Primary in vitro screening of inhibitory activity of the synthesized compounds against blood clotting factors Xa, XIa and thrombin was carried out. Efficient dual inhibitors of factors Xa and XIa and factor Xa and thrombin were identified. [ABSTRACT FROM AUTHOR]

This study introduces a novel class of hybrid compounds, namely, benzothieno[3,2'-f][1,3]oxazepines and their isomeric 2-oxo-2H-spiro[benzothiophene-3,3'-pyrrolines]. The synthetic strategy employs a three-component reaction and 1,4-Dipolar cycloaddition, yielding spiro and oxazepine compounds. Structural elucidation via NMR and MS analyses is complemented by X-ray crystallography and a proposed mechanistic pathway. Biological evaluation against HEK-293 and HT-29 cells reveals potent and selective cytotoxicity against HEK-293 without cytotoxic effects against HT-29 cells. Compound 16c exhibited the highest cytotoxic properties with IC50 = 4.30 μM against HEK-293 cells. Accordingly, the new compounds can be considered as promising leads for possible optimization into novel selective cytotoxic treatments. [ABSTRACT FROM AUTHOR]

This article discusses a method for synthesizing tetracyclic dihydrochromeno[2,3-b]pyrrolo[3,4-e]pyridine-triones through a one-step multicomponent reaction. The authors highlight the advantages of this strategy, including short reaction time, higher efficiency, and greater versatility. They also emphasize the biological significance of incorporating multiple heterocyclic moieties into one molecule. The article provides a detailed description of the synthesis process and optimization of reaction conditions. The authors conclude that their method offers a novel and general route to access these compounds. Additionally, the article provides technical information about the synthesis and characterization of three specific compounds, including their physical properties and spectroscopic data. This information is intended for researchers in the field. [Extracted from the article]

This article discusses the synthesis and characterization of a new nanocatalyst called GO@ dopamine-Cu, which is used in the synthesis of dihydrofuran-2(5H)-one derivatives. The nanocatalyst was characterized using various techniques and showed good recyclability and high performance. The synthesis of fully substituted dihydrofuran-2(5H)-ones is important in organic synthesis and has applications in pharmaceuticals and flavors. The document also provides a list of scientific articles related to the synthesis and applications of furan derivatives, which can be valuable for researchers interested in this field. [Extracted from the article]

New C3-substituted 5,6-dihydropyrrolo[2,1-a]isoquinolines have been synthesized via three-com-ponent domino reaction of 1-aroyl-3,4-dihydroisoquinolines, dimethyl acetylenedicarboxylate, and CH acids in anhydrous acetonitrile under microwave irradiation at 130°C. [ABSTRACT FROM AUTHOR]

A simple, one-pot synthesis of six highly functionalized selenazole derivatives has been achieved in moderate to good yields via a three-component condensation of variously substituted hydrazines, potassium selenocyanate, aroyl chlorides, and dimethyl acetylenedicarboxylate in acetone at room temperature. The structures of the compounds were deduced from elemental analysis and their infrared (IR), 77Se nuclear magnetic resonance (NMR), 1H NMR, and 13C NMR spectra. This new protocol offers advantages such as mild reaction conditions, easy work-up, and high yields. [ABSTRACT FROM AUTHOR]

Herein, we reported on a new series of hydrazono bis-4-oxothiazolidines during the reaction of (hydrazinecarbonothioyl)hydrazinecarbothioamides with dimethyl acetylenedicarboxylate in ethanol as a solvent. The products were obtained in good yields. The structure assignment of obtained products was confirmed by NMR, mass and IR spectroscopy in addition to elemental analyses. The structure of the products was also confirmed by a single-crystal X-ray structure analysis. The possible mechanism for the reaction was also discussed. [ABSTRACT FROM AUTHOR]

A new effective method for the synthesis of imidazo[1,5-b]pyridazines derivatives (yields = 68–89%) by the interaction of 1,2-diamino-4-phenylimidazole with DMAD, in methanol and in the presence of a catalytic amount of acetic acid, is proposed. The course of reaction has been examined by classical organic methods, HPLC-MS analysis, and quantum-chemical calculations. [ABSTRACT FROM AUTHOR]

Reaction between 2-(3,5-dimethylpyrazole-1-carbonyl)-3-arylacrylonitrile and dimethyl acetylenedicarboxylate in the presence of potassium selenocyanate at room temperature provided a simple and efficient one-pot route for the synthesis of six highly functionalized selenophenes. [ABSTRACT FROM AUTHOR]

Methyl (2Z)-[2[(diaminomethylene)amino]-4-oxothiazol-5(4H)-ylidene]acetate was obtained by the reaction of N-amidinothiourea and dimethyl acetylenedicarboxylate (DMAD) under various conditions: methanol, ethanol, acetonitrile, ethyl acetate, dioxane, acetic acid, ethanol/TsOH. The structure of the product has been proven by X-ray diffraction analysis. A series of new N-(5-R-1,3,5-triazinan-2-ylidene)-N-1,3-thiazol-2-amines was obtained as a result of the multicomponent condensation of methyl (2Z)-[2[(diaminomethylene)amino]-4-oxothiazol-5(4H)-ylidene]acetate with alkylamines and formaldehyde. [ABSTRACT FROM AUTHOR]

An efficient synthesis of novel spiro[2-oxobenzofuran-3,3′-pyrrolines] is achieved via a three-component 1,4-dipolar cycloaddition reaction at rt involving benzofuran-2,3-diones, dimethyl acetylenedicarboxylate along with imidazo[1,5-a]pyridine, or imidazo[1,5-a]quinoline or imidazo[5,1-a]isoquinoline. The expected isomeric benzofuro[3,2-f]oxazepines (kinetic control cycloadducts) were, however, not detected. Structures of the title spiro products are evidenced from HRMS and NMR spectral data and further confirmed by single-crystal X-ray crystallography.

Background: A series of novel 2-(isoquinolin-1-yl)-spiro[oxindole-3,3'-pyrrolines] were synthesized by a one-pot three-component reaction involving dimethyl acetylenedicarboxylate, 3- phenylimidazo[5,1-a]isoquinoline and N-alkylisatins in chloroform at ∼60 °C for 24 h., Aims: This study aimed at the synthesis of novel spirooxindole-3,3'-pyrrolines derivatives and in vitro evaluation of cytotoxicity affinities in cross-correlations with their antiinflammation and radical scavenging capacities., Objective: The objective of this study was to use a one-pot, three-component reaction to synthesize a novel set of spirooxindole-3,3'-pyrrolines derivatives., Method: A novel set of spirooxindole-3,3'-pyrrolines (8a-i) was synthesized by a one-pot threecomponent reaction involving dimethyl acetylenedicarboxylate, 3-phenylimidazo[5,1-a]isoquinoline and N-alkylisatins in chloroform at ∼60 °C for 24 h. These new compounds were characterized by 1HNMR, 13C-NMR, and HRMS spectral data and screened for their antitumor, anti-inflammatory, antibacterial, antifungal, and antioxidant activities., Results: The new synthetic spirooxindole-3,3'-pyrrolines (8a-i)-tested compounds displayed significant anti-inflammatory properties and were noncytotoxic on PDL fibroblasts. However, they lacked antioxidative-DPPH radical scavenging capabilities. Notably, Doxorubicin and cisplatin demonstrated antiproliferative effects on various cancer monolayers. Moreover, compounds 8b, 8d, 8f, 8h, and 8i exhibited pronounced viability reduction properties in colorectal and pancreatic cancer monolayers, as well as across skin, lung, prostate, and cervical adenocarcinomas, with higher cytotoxicity in mammary cancer cells MCF7 and T47D. None of the tested compounds had significant antibacterial activity against S. aureus or E. coli. However, compounds 8c, 8d, and 8f exhibited notable antifungal properties, indicating potential for further investigation., Conclusion: Eight new synthetic spiro[indoline-3,3-pyrroles] were prepared, characterized, and evaluated for their anti-inflammatory and cytotoxic properties. The compounds showed significant anti-inflammatory effects and promising cytotoxicity against various cancer monolayers, especially in colorectal and pancreatic cancers. Some compounds also exhibited antifungal properties. However, they did not exhibit significant antibacterial activity., (Copyright© Bentham Science Publishers; For any queries, please email at epub@benthamscience.net.)

Reaction of 2-((4-hydroxy-2-oxo-1,2-dihydroquinolin-3-yl)methylene)hydrazinecarbothioamides with dimethyl acetylenedicarboxylate afforded, in good yields, the corresponding thiazoles derived from 2-quinolones. However, the reaction of N-ethyl-2-quinonylhydrazinecarbothioamide with 2-(bis(methylthio)methylene)malononitrile or its ester derivative gave the corresponding quinolin-3-yl-methylenehydrazono-1,3-thiazines. The proposed mechanism was discussed. The structure of the obtained products was elucidated via NMR, IR and mass spectra as well as elemental analysis. [ABSTRACT FROM AUTHOR]

In this research, a number of new and known chromenopyrano[2,3-b]pyridine derivatives have been prepared. Initially, according to the reported procedure, pyrano[2,3-c]chromene derivatives were synthesized by the reaction between 4-hydroxycoumarin, aromatic aldehydes and malononitrile using silica sodium carbonate (SSC) as the catalyst. Next, the prepared pyrano[2,3-c]chromenes were reacted by dimethyl acetylenedicarboxylate (DMAD) or cyclohexanone in the presence of sodium carbonate to produce chromenopyrano[2,3-b]pyridine derivatives. The presented protocol avoids the use of expensive catalysts and gives useful potentially bioactive heterocycles in excellent to high yields. [ABSTRACT FROM AUTHOR]

A new effective method for the synthesis of imidazo[1,5-b]pyridazines derivatives (yields = 68–89%) by the interaction of 1,2-diamino-4-phenylimidazole with DMAD, in methanol and in the presence of a catalytic amount of acetic acid, is proposed. The course of reaction has been examined by classical organic methods, HPLC-MS analysis, and quantum-chemical calculations.

4,6-Dimethoxy-3-substituted-indole-7-carbaldehydes and 4,6-dimethoxy-3-substituted-indole-2-carbaldehydes undergo reaction with dimethyl acetylenedicarboxylate and triphenylphosphine to give the corresponding pyrroloquinolines and pyrroloindoles respectively. In the case of an indole-2,7-dicarbaldehyde, reaction at the 2-carbaldehyde is preferred, giving the related pyrroloindole. In the case of a 6-hydroxy-4-methoxy-3-substituted-indole-7-carbaldehyde formation of a pyrroloquinoline is preferred to cyclisation on to the phenolic group to generate a pyranoindole. The pyrroloquinolines and pyrroloindoles are highly fluorescent. [ABSTRACT FROM AUTHOR]

Pyrimidine derivatives have biological and pharmacological properties. Therefore, in this study we focused on the synthesis various Pyrimidine derivatives to make noteworthy contributions this class of heterocyclic compounds. In the present study, the new compounds (4-6) were obtained by the reactions of 1-amino-5-benzoyl-4-phenylpyrimidin-2(1H)-one (1), 1-amino-5- (4-methylbenzoyl)-4-(4-methylphenyl)pyrimidin-2(1H)-one (2) and 1-amino-5-(4-methoxybenzoyl)- 4-(4-methoxyphenyl)pyrimidin-2(1H)-one (3) with dimethyl acetylenedicarboxylate. The structures of these compounds were proved by elemental analysis, FT-IR, ¹H and 13C-NMR spectra. In addition to, quantum chemical calculations were made to find molecular properties of the pyrimidin-1(2H)- ylaminofumarate derivatives (4-6) by using DFT/B3LYP method with 6-311++G(2d,2p) basis set. Quantum chemical features such as EHOMO, ELUMO, energy gap, ionization potential, chemical hardness, chemical softness, electronegativity etc. values for gas and solvent phase of neutral molecules were calculated and discussed. [ABSTRACT FROM AUTHOR]

Reaction between arylidenemalononitriles and dimethyl acetylenedicarboxylate in the presence of KSeCN at room temperature provided a simple and efficient one-pot route for the synthesis of highly functionalized selenophenes. The reaction is characterized by mild conditions, short reaction time, and tolerance to various functional groups. [ABSTRACT FROM AUTHOR]

One of the commonly used methods to synthesize furans is the three‐component reaction among aromatic aldehyde, arylamine, and acetylenedicarboxylate. The main advantages of this work are easy reaction work‐up, short reaction time, high yield and easy recyclability, reusability of the catalyst. And also basalt fiber applications are surely innovative in many industrial and economic fields, because of its good mechanical, chemical and thermal performances. [ABSTRACT FROM AUTHOR]

A Selected set of 2-(quinolin-2-yl)-1,3-oxazepino[7,6-b]indoles 4a–d and dihydroacenaphtho[1,2-f][1,3]oxazepine 5 have been prepared via 1,4-dipolar cycloaddition reaction involving 1-phenylimidazo[1,5-a]quinoline, dimethyl acetylenedicarboxylate, and N-(substituted)isatins or acenaphthoquinone. Structures of the new heterocycles 4a–d and 5 are supported by NMR and HRMS spectral data, and confirmed by single-crystal X-ray crystallography for 4c and 5. [ABSTRACT FROM AUTHOR]

The title compound, 2,2’-[(1,4-dimethoxy-1,4-dioxobutane-2,3-diylidene)bis(azanylylidene)]bis(quinoline-3-carboxylic acid) was synthesized from isoxazolo[3,4-b]quinolin-3(1H)-one and dimethyl acetylenedicarboxylate (DMAD) via a double aza-Michael addition followed by [1,3]-H shifts. The product was characterized by infrared and nuclear magnetic resonance spectroscopy, as well as elemental analysis and high-resolution mass spectrometry (HRMS). The proposed reaction mechanism was rationalized by density functional theory (DFT) calculations.

Synthesis of novel tetrahydroquinazoline-2-carboxylate and arylaminoquinazoline-2-carboxylate in good yields has been established via the nucleophilic cycloaddition of 2-amino-N′-arylbenzimidamides on dimethyl acetylenedicarboxylate. Moreover, studying the reaction of 2-amino-N′-arylbenzimidamides with 2-(dicyanomethylene)indan-1,3-dione to give 3,4-dihydroquinazolin derivatives. The results obtained from IR, 1H NMR, and 13C NMR data as well as the mass spectra are in agreement with the assigned structures. A plausible mechanism for the formation of the products is presented. [ABSTRACT FROM AUTHOR]

Double Mannich bases obtained from α-indanone and α-tetralone contain a bis-β-amino ketone fragment and are promising intermediate compounds for the synthesis of nitrogen heterocycles via reactions with dimethyl acetylenedicarboxylate and methyl propiolate. The products of these reactions are determined by the activated acetylene structure. The reaction begins with attack of the activated acetylenic compound on the tertiary nitrogen atom of the Mannich base to give 1,3-zwitterionic intermediate. The subsequent domino reaction is driven by neutralization of the charge on the nitrogen atom through formation and/or rupture of several C–C bonds. Intramolecular attack of the negatively charged center of the 1,3-zwitterion derived from the indanone base and dimethyl acetylenedicarboxylate on the carbonyl carbon atom of the indanone fragment is followed by domino process, leading to the formation of dimethyl 2-methyl-1,2-dihydro-9H-indeno[2,1-c]-pyridine-3,4-dicarboxylate. The reaction of the same Mannich base with methyl propiolate involves 1,3-sigma-tropic rearrangement with neutralization of the positive charge on the nitrogen atom in the intermediate structure and negative charge transfer to the carbonyl oxygen atom. Next follows aldolization/crotonization with the second β-amino carbonyl fragment to produce methyl 2′-methyl-1-oxo-1,1′,2′,3,5′,11′-hexahydrospiro-[indene-2,6′-indeno[2,1-c]azocine]-4′-carboxylate. One more reaction direction leading to the formation of linear enamines via intramolecular proton migration from the indan fragment to the C-anionic center in the 1,3-zwitterion with simultaneous elimination of 2-methylideneindan-1-one has been revealed by HPLC/MS analysis of both reaction mixtures. Such enamines, methyl 3-{methyl[(1-oxo-1,2,3,4-tetrahydronaphthalen-2-yl)methyl]amino}prop-2-enoate and dimethyl (2Z)-2-{methyl[(1-oxo-1,2,3,4-tetrahydronaphthalen-2-yl)-methyl]amino}but-2-enedioate, were isolated in the reactions of activated acetylenic compounds with the Mannich base derived from tetralone. Previously described synthesis of 1-azabicyclo[3.3.1]nonanes from Mannich bases has been reproduced, and detailed analysis of the reaction mixtures has revealed products resulting from elimination of one alkylaryl group from the zwitterionic intermediate. The formation of linear enamines, dimethyl (2Z)-2-[methyl(3-oxo-3-phenylpropyl)amino]but-2-enedioate and dimethyl (2Z)-2-{methyl-[3-oxo-3-(thiophen-2-yl)propyl]amino}but-2-enediate, suggests facile retro-aldol reaction of 3-aroyl-4-aryl-1-methylpiperidin-4-ols as the necessary step. PASS online predicted diverse biological activities of all newly synthesized compounds with a probability of 65–80%. [ABSTRACT FROM AUTHOR]

1,2,3,4,5-Pentacarbomethoxycyclopentadiene (PCCP) is a strong organic acid and a precursor to useful organocatalysts, including chiral Brønsted acids and silicon-based Lewis acids. The synthetic route to PCCP, first reported in 1942, is inconvenient for a number of reasons. The two-step synthesis requires the purification of intermediates from intractable side-products, high reaction temperatures, and extensive labor (3 days). We have developed an improved procedure that delivers PCCP efficiently in 24 hours in one pot at ambient temperature and without isolation. [ABSTRACT FROM AUTHOR]

Graphical abstract Abstract 2-Substituted hydrazinecarbothioamides and N ,2-disubstituted hydrazinecarbothioamides react in high yield with dimethyl acetylenedicarboxylate (DMAD) to give 4-oxo- Z -(thiazolidin-5-ylidene) acetate derivatives. Several mechanistic options involving interaction are presented. The structures of thiazolidin-4-ones have been unambiguously confirmed by single crystal X-ray crystallography. [ABSTRACT FROM AUTHOR]

The kinetics of the reaction between para-substituted anilines and dimethyl acetylenedicarboxylate (DMAD) with derivatives of benzaldehyde for the one-pot formation of 3,4,5-substituted furan-2(5H)-ones in the presence of lactic acid as a catalyst have been studied spectrophotometrically at different temperatures. A mechanism involving four steps was proposed for the reactions, all of which followed second-order kinetics. The partial orders with respect to substituted aniline and DMAD were one and one and the reactions revealed zeroorder kinetics for benzaldehyde and its derivatives. Changing of substituents on benzaldehyde left rates of reaction unaffected. However, various substituents on aniline showed that para electron-withdrawing groups decreased the rate of reaction. According to investigation of an isokinetic relationship, a common mechanism exists for all studied substituents and a general mechanism can be formulated. Kinetic values (k and Ea) and associated activation parameters (ΔG‡, ΔS‡ and ΔH‡) of the reactions were determined. [ABSTRACT FROM AUTHOR]

4-Carboxybenzyl sulfamic acid functionalized Fe 3 O 4 nanoparticles as a novel catalyst was manufactured. This catalyst was characterized and evaluated in the one-pot synthesis of furan-2(5 H )-one derivatives from dimethyl acetylenedicarboxylate, aryl aldehydes, and various anilines in terms of activity and reusability. The catalyst showed high catalytic activity, good recoverability and reusability, thermal stability and provides clean production of fine furan-2(5 H )-one derivatives in short reaction times. The heterogeneous catalyst could be used at least five times without significant loss of its activity. [ABSTRACT FROM AUTHOR]

Transformations of 2-methyl-1-phenylethynyl-1,2,3,4-tetrahydroisoquinoline resulting from the action of activated alkynes in trifluoroethanol and hexafluoroisopropanol were studied. In reactions with dimethyl acetylenedicarboxylate, 6-phenylethynyl-substituted benzazocines were prepared, while methyl 4-benzyl-5-(2-ethenylphenyl)-1-methyl-1H-pyrrole-3-carboxylate and benzo[d][3]-azacyclodeca[4,6,7]triene with the allene fragment, respectively, were isolated in reactions with methyl propiolate and acetylacetylene in addition to the corresponding benzazocines. As a rule, in hexafluoroisopropanol, the yields of azocines are higher. In reaction with acetylacetylene in dichloromethane, 1-(2-acetylvinyl)-1-phenylethynyltetrahydroisoquinoline is formed in high yield. [ABSTRACT FROM AUTHOR]

A kinetic and mechanistic investigation, using conventional UV-Vis spectrophotometry, of the reaction between dimethyl acetylenedicarboxylate (DMAD) and 1,3-dicarbonyl compounds including acetylacetone (ACAC) and dibenzoylmethane (DBM), has been conducted in a methanol environment with triphenylarsine (TPA) acting as a catalyst. Previously, in a similar reaction, triphenylphosphine (TPP) (instead of TPA) had been employed as a reactant (not a catalyst) for the generation of an ylide (final product). In the present work, of significance is the differential behaviour of TPA which, as a catalyst in the reaction environment, leads to a cyclopropane compound. Of other significance is the different behaviours of the two reactants in the kinetics and mechanism of the reaction. In previous work, TPP acted as a weak nucleophile (a reactant), so the first step of the reaction was recognised as the rate-determining step (RDS). Here, TPA reacts as a stronger nucleophile and a catalyst, resulting in the fourth step of the reaction (step4, k4, a proton transfer process) being recognised as the RDS. The reaction followed second-order kinetics. The proposed mechanism was adapted in accord with the experimental results and the steady-state assumption. The results showed that the reaction rate decreases in the presence of DBM, which participates in the second step (step2), compared to ACAC when it is present as another 1,3-dicarbonyl compound (structural effect). In addition, in previous work, the partial order of the reaction with respect to the 1,3-dicarbonyl compound was zero, while it is one in the present work. As a significant result, not only did a change in the structure of one of the reactants (TPA instead of TPP) create a different product, but also the kinetics and reaction mechanism changed. In addition, the reaction is enthalpy-controlled. [ABSTRACT FROM AUTHOR]

3,10-Dihydro-2 H -1,3-oxazepino[7,6- b ]indoles are synthesized via a convenient one-pot three-component 1,4-dipolar cycloaddition reaction, involving 3-alkyl(aryl)imidazo[1,5- a ]pyridines, dimethyl acetylenedicarboxylate (DMAD) and N -alkylisatins. Structures of the newly synthesized heterocycles are evidenced from spectral data and further confirmed by single crystal X-ray diffraction. A plausible reaction mechanism is advanced, whereby the intermediate 1,4-dipole, generated in situ from imidazo[1,5- a ]pyridine and DMAD, initially adds to the keto group of N -alkylisatins to form the corresponding 1,3-oxazin-spiro-oxindole cycloadduct. The latter undergoes subsequent unprecedented skeletal rearrangement through a cascade of bond breaking and bond making processes, eventually leading to ring enlargement, furnishing the tricyclic oxazepino[7,6- b ]indole ring system as the end product. [ABSTRACT FROM AUTHOR]