Reaction Of Isoquinoline Research Articles

Coordination complexes of isoquinoline with cobalt and nickel halides

Reaction of isoquinoline (iQuin) with cobalt(II) and nickel(II) chloride and bromide produced a family of neutral coordination complexes: (iQuin)2CoX2 [X = Cl (1), Br (2)], (iQuin)4CoX2 (X = Cl (3), X = Br (4)], (iQuin)4NiX2 [X = Cl, (5), X = Br, (6)], and (iQuin)2NiBr2(CH3CN)2 (7). The crystal structures of 1–5 and 7 are reported. The majority of the compounds crystallize with some of the iQuin ligands undergoing a ∼2-fold rotational disorder, likely caused by the nearly equivalent space occupied by the two positions. The disorder is temperature independent and ∼50:50 in all cases but one. Magnetic measurements for all seven compounds indicate that their behavior is dominated by single-ion anisotropy effects with indications of antiferromagnetic exchange also present in 1 and 2.

Synthesis, reaction, antimicrobial, and docking study of new chalcones incorporating isoquinoline moiety

Reaction of isoquinoline 1 with hydrazonoyl chlorides 2A–E gave the corresponding triazoloisoquinolines 4A–E. The latter products 4A–E were reacted with 4-(piperidin-1-yl)benzaldehyde 5a and 4-morpholinobenzaldehyde 5b to afford the corresponding chalcones 6a,b. Some of chalcones 6 were reacted with hydrazine hydrate in refluxing ethanol to give the corresponding 8,9-dimethoxy-1-aryl-4,5-dihydro-1H-pyrazol-3-yl-1,5,6,10b-tetrahydro-[1,2,4]triazolo[3,4-a]isoquinoline derivatives 7A–C. Antimicrobial studies were performed using gram-negative bacteria (Escherichia coli) and (Klebsiella pneumonia), a gram-positive bacteria (Streptococcus mutans) and (Staphylococcus aureus), filamentous fungus (Asperagillus Nigar) and yeast (Candida albicans). Data revealed that chalcone 6Aa achieved the lowest MIC values (high efficient derivative) against the sensitive bacterial strain E. coli with MIC value 130 µg/ml. The most effective compound 6Aa, which demonstrated the highest binding affinity toward tested protein [thymidine phosphorylase enzyme, (PDB ID:4EAD)], was docked using MOE 2014.09 software.

Production of Pyrimidobenzazepine Derivatives and Reduction of Organic Pollutant Using Ag/Fe3O4/TiO2/CuO@MWCNTs MNCs

The Petasites hybridus rhizome water extract as green media was used for the preparation of the Ag/Fe3O4/TiO2/CuO@MWCNTs magnetic nanocomposites and its activity was evaluated by using in the one-pot multicomponent reaction of isoquinoline, α-haloketones, 2-amino benzoic acids, diethyl carbonate, electron deficient acetylenic compounds, ammonium acetate, and tert-butyl isocyanide in water at room temperature for the production of novel derivatives of pyrimidobenzazepines in excellent yields. Moreover, reduction of organic pollutants such 4-nitrophenol was performed by synthesized Ag/Fe3O4/TiO2/CuO@MWCNTs in water at room temperature. The outcomes showed this catalyst was decreased organic pollutants in few seconds. Because of having azepine moiety, the synthesized compounds show good antioxidant activity. These synthesized compounds also displayed antimicrobial activity by using the disk diffusion procedure and two Gram-positive and Gram-negative bacteria. The employed process for production of benzazepines has some benefits such as short time of reactions, excellent efficiency of product, easy separation of catalyst and products.

A Convenient Synthesis of Polysubstituted Coumarin‐pyrrolo[2,1‐a]isoquinoline‐1‐carbaldehydes from Isoquinoline, 2‐Bromoacetophenones and Coumarin‐β‐chlorovinyl Aldehydes

AbstractIn this research, a simple and efficient strategy for the straightforward synthesis of polysubstituted coumarin‐pyrrolo[2,1‐a]isoquinoline‐1‐carbaldehydes is presented by a sequential three‐component reaction of isoquinoline, 2‐bromoacetophenones and 3‐chloro‐3‐(2‐oxo‐2H‐chromen‐3‐yl)acrylaldehydes as readily available starting materials, which includes base‐mediated 1,4‐addition or [3+2] cycloaddition/intramolecular cyclization/formation two C−C bonds/aromatization tandem reaction under air. In this method, chemoselective cascade process, easily accessible starting materials, energy conserving (short reaction times at room temperature), simplicity of product purification (the products can be purified by washing with EtOH), excellent yields (75–88 %), metal‐free catalyst, green and mild conditions in one‐pot are important highlighted advantages of this protocol.

A review of the synthesis of 1,2-dihydroisoquinoline, [2,1-a] isoquinoline and [5,1-a] isoquinoline since 2006

The synthesis of 1,2-dihydroisoquinoline, [2,1-a] isoquinoline and [5,1-a] isoquinoline is very important because of their biological and medicinal activities as well as their conversion to corresponding isoquinoline. Various nucleophiles and pronucleophiles could be added to Ortho-alkynylbenzaldehydes, ortho-alkynylaryl aldimines and ortho-alkynylbenzaldoximes in the presence of different Lewis acids and generate derivatives of 1,2-dihydroisoquinoline in tandem route. Also, 1,4-dipolar intermediate which synthesized from the reaction of isoquinoline and electron-deficient compounds reacted with various dipolarophiles for the formation of five- and six-membered heterocycles including [2,1-a] isoquinoline and [5,1-a] isoquinoline. In recent years, these interesting zwitterions have been used in multicomponent reactions to produce a considerable number of heterocyclic compounds. In this review, I have classified a variety of methods since 2006 until now, for the generation of 1,2-dihydroisoquinoline, [2,1-a] isoquinoline and [5,1-a] isoquinoline via the above routes.

Convenient Construction of Spiro[pyrazole‐4,1′‐pyrido[2,1‐a]isoquinoline] and Spiro[pyrazole‐4,4′‐pyrido[1,2‐a]quinoline] via Three‐Component Reaction

AbstractThe three‐component reaction of isoquinoline, dialkyl but‐2‐ynedioate and 4‐arylidene‐5‐methyl‐2‐phenylpyrazol‐3‐ones in acetonitrile at room temperature gave functionalized spiro[pyrazole‐4,1′‐pyrido[2,1‐a]isoquinolines] in satisfactory yields with cis/cis‐diastereoisomer as major product. On the other hand, the similar three‐component reaction with quinoline afforded both cis/cis‐ and cis/trans‐isomeric spiro[pyrazole‐4,4′‐pyrido[1,2‐a]quinolines] in nearly comparable yields. The reaction was finished with in situ generation of Huisgen’ 1,4‐dipole, sequential Michael addition and annulation reaction process.

KF/Clinoptilolite Nanoparticles as a Heterogeneous Catalyst for Green Synthesis of pyrido[2,1-a]isoquinolines using Four-Component Reaction of Alkyl Bromides.

KF/Clinoptilolite nanoparticles are employed as a heterogeneous catalyst for the preparation of pyrido[2,1-a]isoquinoline derivatives through a four-component reaction of isoquinoline, two different alkyl bromides and an electron deficient internal alkynes at ambient temperature in water as green solvent. In this research, (2,2-Diphenyl-1-picrylhydrazyl) radical trapping and reducing potential of ferric ion experiments was used for determining antioxidant activity of some newly synthesized compounds such as 5a, 5c, 5f and 5g and comparing results with synthetic antioxidants (TBHQ and BHT). Compounds 5a, 5c, 5f and 5g display trace DPPH radical trapping and excellent reducing power of ferric ion. Furthermore, the power of some prepared compounds against Gram-positive and Gram-negative bacteria was proved by employing the disk dispersion experiment. The obtained results of disk diffusion test showed that compounds 5a, 5d and 5e prevented the bacterial growth. The reported procedure shows the advantages of clean reaction, high yield and simple purification.

Bio-Fe3O4-MNPs catalyzed green synthesis of pyrrolo[2,1-a]isoquinoline derivatives using isoquinolium bromide salts: study of antioxidant activity

In this research, a novel, one-pot, efficient procedure with high yield for the synthesis of pyrrolo[2,1-a]isoquinoline derivatives using multi-component reaction of isoquinoline, alkyl bromides, and triphenylphosphine in the presence of Fe3O4-MNPs as catalyst under solvent-free conditions at room temperature is investigated. This study highlights an easy, simple, rapid, and clean method for the preparation of pyrrolo[2,1-a]isoquinoline derivatives. The Fe3O4-MNPs in these reactions were produced employing a green procedure by reduction of ferric chloride solution with pomegranate peel water extract. Additionally, antioxidant activity was studied for the some newly synthesized compounds such as 5a–5d using the DPPH radical trapping and reducing potential of ferric ion experiments and comparing the results with the results of synthetic antioxidants (2-tert-butylhydroquinone, TBHQ; butylated hydroxytoluene, BHT). As a result, compounds 5a–5d show trace DPPH radical trapping and excellent reducing power of ferric ion.

Green synthesis of pyrimido‐isoquinolines and pyrimido‐quinoline using ZnO nanorods as an efficient catalyst: Study of antioxidant activity

In this paper, we report the synthesis of pyrimido[2,1‐a] isoquinoline and pyrimido[1,2‐a]quinoline derivatives in high yields from the reaction of isoquinoline or quinoline, activated acetylenic compounds, and amides in the presence of ZnO nanorods (ZnO‐NRs) as catalyst under solvent‐free conditions at room temperature. ZnO‐NRs show good improvement in the yield of the product and significant reusability. Also, the antioxidant activities of the some of the newly synthesized compounds were carried out by 1,1‐diphenyl‐2‐picrylhydrazyl (PDDH) radical trapping and ferric ion reducing potential tests and compared with those of the synthetic antioxidants 2‐tert‐butylhydroquinone (TBHQ) and butylated hydroxytoluene (BHT). These compounds do not show good DPPH radical scavenging but display good ferric ion reducing power.

The Effect of Spatial Hindrance on Stereoselective Synthesis of Real Enaminoesters and Determination of the Relative Stability of the Two E- and Z-Isomers of Hypothetical Enaminoesters

The three-component reactions of isoquinoline and acetylenic esters in the presence of 2-tert-butyl-4-methylphenol has been investigated. The reactions were proceeded smoothly at room temperature without the usage of a catalyst. The structures of the synthesized compounds were characterized by elemental analyses and spectral studies. Also, quantum mechanical calculations were carried out using the ab initio and DFT methods at the HF/6-31G (d,p) and B3LYP/6-31G (d,p) levels of theory to determine the stability of the two E and Z-isomers from both the hypothetical and real reactions between phenantridine or isoquinoline and dimethyl acetylendicarboxylate in the presence of phenol derivatives for the generation of enaminoesters, in both gas phase and solvent media (polar and nonpolar). The results showed that more effective hindrance of any reactants (phenol derivatives, acetylenic esters and phenantridine or isoquinoline) should be considered for the generation of highly stereoselective enaminoester (E-isomer) in real or hypothetical synthesis. To reduce the effect of spatial hindrance on all cases (real or hypothetical synthesis) of E-enaminoester, corresponding to its more stability, the hydrogen atom and phenanthridine (or isoquinoline) moieties were positioned on the side of the double bond within the structure of an enaminoester. The E-isomers were recognized as the preferential form of the highly stable enaminoester and they can be considered as an effective product that has biological activity.

A Synthesis of Spirocyclic Oxazinoisoquinolines and Oxazinoquinolines Bearing Thiazolopyrimidine Moieties

The reaction of isoquinoline or quinoline with dialkyl acetylenedicarboxylates in the presence of alkyl 2-{3,5-dioxo-5H-thiazolo[3,2-a]pyrimidin-2(3H)-ylidene}acetates (generated in situ from acetylenedicarboxylates and 2-thiouracils) led to dialkyl 2-(2-alkoxy-2-oxoethylidene)-5-oxo-2H,5H,11b′H-spiro{thiazolo[3,2-a]pyrimidine-3,2′-[1,3]oxazino[2,3-a]isoquinoline}-3′,4′-dicarboxylates or dialkyl 2-(2-alkoxy-2-oxoethylidene)-5-oxo-2H,4a′H,5H-spiro{thiazolo[3,2-a]pyrimidine-3,2′-[1,3]oxazino[3,2-a]quinoline}-1′,2′-dicarboxylates in good yields. The structure of the target compounds was confirmed by X-ray diffraction study.

Green Synthesis of Pyrido[2,1-a]isoquinolines and Pyrido[1,2-a]quinolines by Using ZnO Nanoparticles

Pyrido[2,1-a]isoquinoline and pyrido[1,2-a]quinoline derivatives have been produced in good yields by the reaction of isoquinoline or quinoline, activated acetylenic compounds, α-halo ketones, and triphenylphosphine in the presence of ZnO nanoparticles (NPs) as an efficient catalyst under solvent-free conditions at room temperature. The reaction workup is easy, and the products can be readily separated from the reaction mixture. ZnO NPs markedly improved the yield of the product. The catalyst showed significant reusable activity.

Synthesis and Photophysical Properties of 3-(Trifluoromethyl)-2H-imidazo[5,1-a]isoquinolinium Chloride Derivatives

A series of novel blue-light-emitting 2H-imidazo[5,1-a]isoquinolinium chloride derivatives were synthesized by the reaction of isoquinoline with trifluoroacetimidoyl chlorides and isocyanides in dry CH2Cl2 in excellent yields. Fluorescence studies showed that the compounds absorb UV radiation and then emit blue light at about 481 nm with moderate to good fluorescence quantum yields. These compounds also showed high Stokes shifts, and can be used to develop ­ultrasensitive fluorescent molecular probes to study a variety of biological events and processes.

Construction of Spiropyrido[2, 1‐a]isoquinoline via Tandem Reactions of Huisgen's 1,4‐Dipoles with Various Alkene Dipolarophiles

AbstractThe three‐component reaction of isoquinoline, dimethyl acetylenedicarboxylate and arylidene pivaloylacetonitrile in acetonitrile at room temperature afforded pyrido[2, 1‐a]isoquinolines 1 a‐1 j in good yields and with high diastereoselectivity. When arylidene‐substituted 1,3‐indanediones, Meldrum acids, and N,N’‐dimethylbarbituric acids were employed in the reaction, the novel functionalized spiro[indene‐2, 1′‐pyrido[2, 1‐a]isoquinolines] 2 a‐2 j, spiro[pyrido[2, 1‐a]isoquinoline‐1,5′‐[1, 3]dioxanes] 3 a‐3 h and spiro[pyrido[2, 1‐a]isoquinoline‐1,5′‐pyrimidines] 4 a‐4 e were also efficiently synthesized in satisfactory yields. The reaction mechanism included domino formation of Huisgen's 1,4‐dipole, Michael addition and cyclization processes.

ChemInform Abstract: A Diastereoselective Synthesis of Functionalized Tetrahydroindeno[2′,1′,3,4]pyrido[2,1‐a]isoquinolines

Abstractby one‐pot four‐component reaction of isoquinoline and alkyl propynoates with two equivalents indanedione

A Diastereoselective Synthesis of Functionalized Tetrahydroindeno[2′,1′,3,4]pyrido[2,1‐a]isoquinolines

AbstractAn effective route to alkyl 9a‐(2,3‐dihydro‐1,3‐dioxo‐1H‐inden‐2‐yl)‐9a,14,14a,14b‐tetrahydro‐14‐oxoindeno[2′,1′:3,4]pyrido[2,1‐a]isoquinoline‐9‐carboxylates via a diastereoselective one‐pot four‐component reaction of isoquinoline and alkyl prop‐2‐ynoates with two equivalents of indane‐1,3‐dione, in aqueous MeOH at room temperature, is described.

ChemInform Abstract: Three‐Component Synthesis and Antibacterial Evaluation of Some Novel 1,2‐Dihydroisoquinoline Derivatives.

AbstractAn efficient and simple method for the synthesis of the title compounds (IV), (VI) is developed using the three‐component reaction of isoquinoline (I), activated acetylenes (II) in the presence of kojic acid (III) or 8‐hydroxyquinolone (V) as OH‐acids.

ChemInform Abstract: A Highly Enantioselective Acyl‐Mannich Reaction of Isoquinolines with Aldehydes Promoted by Proline Derivatives: An Approach to 13‐Alkyl‐tetrahydroprotoberberine Alkaloids.

AbstractThe new method affords alkylated isoquinolines as diastereomeric mixtures with high enantioselectivities.

A Three‐Component Reaction for the Efficient Construction of the 2′,11b′‐Dihydrospiro[indoline‐3,1′‐pyrido[2,1‐a]isoquinoline] Skeleton

The three‐component reactions of isoquinoline, acetylenedicarboxylates, and 3‐phenacylideneoxindoles in ethanol at room temperature resulted in a mixture of two diastereoisomers of 2′,11b′‐dihydrospiro[indoline‐3,1′‐pyrido[2,1‐a]isoquinoline] derivatives, which were successfully separated and characterized. The regioselectivity and diastereoselectivity of this reaction were briefly discussed.

ChemInform Abstract: The Anion‐Binding Approach to Catalytic Enantioselective Acyl Transfer

AbstractReview: [42 refs.