Mohammad reza Mohammadizadeh

Mohammad reza Mohammadizadeh
Persian Gulf University | PGU · Department of Chemistry

Associate Professor

About

88
Publications
11,384
Reads
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1,577
Citations
Citations since 2016
15 Research Items
465 Citations
20162017201820192020202120220204060
20162017201820192020202120220204060
20162017201820192020202120220204060
20162017201820192020202120220204060
Introduction
Mohammad reza Mohammadizadeh currently works at the Department of Chemistry, Persian Gulf University. Mohammad does research in Green Chemistry, Organic Chemistry and Catalysis. Their most recent publication is 'Catalyst-free, efficient, and green procedure for the synthesis of 5-heterocyclic substituted 6-aminouracils'.

Publications

Publications (88)
Article
One-pot three components effective methods are reported for the synthesis of two important families of organic compounds, 2H-pyrrolo[2,3-d]pyrimidine-2,4(3H)-diones substituted 5-(3-hydroxy-1,4-naphthoquinonyl) and 1H-benzo[f]indole-4,9-diones substituted 3-(3-hydroxy-1,4-naphthoquinonyl), by employment of new starting materials. The formers were p...
Article
A mild, efficient and stereoselective synthesis of dialkyl 2‐thiofumarates is described based on the addition reaction of aryl(benzyl) thiols and dialkyl acetylenedicarboxylates in the presence of triethylamine as a mild base. The reactions were stereoselectively performed in CH2Cl2 at room temperature toward synthesis of Z‐stereoimers as the major...
Article
Full-text available
A mild and one-pot synthetic pathway was successfully developed for the synthesis of new naphthoate-based scaffolds containing quinoline, pyranone and cyclohexenone moieties via a multistep reaction between acenaphthoquinone and various 1,3-diketones in the presence of different primary aliphatic and benzylic alcohols. This reaction proceeds via a...
Article
A one-pot route for the synthesis of spiro-isobenzofuran compounds was developed via the condensation reaction of ninhydrin with 4-amino-1,2-naphthoquinones or 2-amino-1,4-naphthoquinones in acetic acid followed by the oxidative cleavage of the corresponding vicinal diols at room temperature. Various derivatives of spiro[benzo[g]indole-2,1′-isobenz...
Article
Full-text available
A one-pot, clean and green procedure is described for the syntheses of new azocine derivatives via addition reactions of enaminones with acenaphthoquinone followed by periodic acid-mediated oxidative cleavages of the corresponding vicinal diols. Various derivatives of azocine were prepared and well characterized. The excellent yields, simple synthe...
Article
A novel and efficient procedure was introduced for the synthesis of alkyl acetates bearing arylthio and quinoxaline moieties from the reaction of o‐phenylenediamines, dialkyl acetylenedicarboxylates, and in‐situ generated arylsulphenyl chlorides in DMF as solvent at room temperature. The procedure worked well for a variety of starting materials and...
Article
The results of our investigations on the preparation of 3a,8a‐dihydroxyindeno[1,2‐d]imidazole derivatives via reaction of thiourea, ninhydrin, and alkyl/benzyl chlorides in aqueous ethanol and under convenient conditions is reported. On the other hand, when guanidinium chloride was used instead of thiourea, the reaction mixtures reached with unexpe...
Article
In this paper, the results of our studies on the catalyst-free synthesis of some new 6-aminouracils bearing naphthoquinone, benzo[a]phenazine, benzo[f]pyrido[2,3-b]quinoxaline, and benzo[f]quinoxaline substituents are reported. At first, 6-amino-5-(3,4-dioxo-1-naphthalenyl)uracil derivatives were synthesized from the reaction of various 6-aminourac...
Article
Oxidation of some derivatives of 4b,9b–dihydroxyindeno[1,2-b]benzofuran-10-one have been investigated in detail using lead(IV) acetate in acetic acid under reflux conditions and periodic acid in aqueous ethanol at room temperature. We realized that during the first 5–15 minutes of the oxidation reactions in lead(IV) acetate/acetic acid system, 3H,3...
Article
The fact that oxidation, as one of the main routes of phase I metabolism of drugs, follows by conjugation reactions, and also formation of nitrenium ion as one of the clozapine oxidation products, directed us to investigate the oxidation of clozapine (CLZ) in the presence of nucleophile. The oxidation of clozapine (CLZ) has been studied on a glassy...
Article
The oxidation of 3a,8a-dihydroxy-2-(alkyl/benzylthio)indeno[1,2-d]imidazol-8(3H)-ones to give the corresponding 3-(alkyl/benzylthio)-9b-hydroxy-1H-imidazo[5,1-a]isoindole-1,5(9bH)-dione derivatives in good to excellent yields at room temperature using two oxidants, periodic acid in aqueous ethanol and lead(IV) acetate in acetic acid, has been repor...
Article
Condensation reaction between ninhydrin and various 1,3-dicarbonyl compounds followed by oxidative cleavage of furans (III) afford the title compounds.
Article
An efficient procedure to reduce sulfoxides using ascorbic acid has been developed. Using this procedure structurally diverse sulfoxides were reduced by treating with ascorbic acid in the presence of a catalytic amount of N-bromosuccinimide (NBS) at room temperature in high yields.
Article
A simple and efficient procedure for the synthesis of 5-methyl-3,3′-dioxo-3H,3′H-spiro[furan-2,1′-isobenzofuran]-3,3′-dione derivatives, proceeding via a condensation reaction between ninhydrin and various 1,3-dicarbonyl compounds followed by oxidative cleavage of the corresponding 3a,8b-dihydroxy-2-methyl-4-oxo-4,8b-dihydro-3aH-indeno[1,2-b]furans...
Article
A diastereoselective synthesis of some new N-containing heterocyclic compounds, indeno[2″,1″: 4′,5′]furo[3′,2′: 5,6]pyrido[2,3-d]pyrimidine-2,4,6(1H,3H)-trione derivatives, is presented. Products were obtained in good to excellent yields by the reaction of amino(thio)uracils with 2-hydroxy-2-(3-oxobut-1-en-2-yl)-2H-indene-1,3-dione in AcOH under re...
Article
An efficient method for the deoxygenation of sulfoxides into their corresponding sulfides at room temperature using NaHSO3 in the presence of catalytic I2 has been reported.
Article
Full-text available
This paper reports a new and simple procedure for the synthesis of 3H-spiro[isobenzofuran-1,3′-pyrazole] derivatives by reacting 1-benzylidene-2-phenylhydrazine derivatives with ninhydrin in acetic acid medium at room temperature followed by oxidative cleavage of their corresponding dihydroindeno[1,2-c]pyrazoles. 1-Benzylidene-2-phenylhydrazine der...
Article
Abstract Symmetric disulfides are produced by treating their corresponding organic halides including benzylic, allylic, primary and secondary halides with Na2S·3H2O and C2Cl6 or CCl4 in PEG-200 at room temperature in high yields.
Article
Full-text available
A one-pot, and scalable method to prepare symmetric disulfides from their corresponding primary, secondary, allylic, and benzylic halides has been developed. In this method, a disulfide is synthesized by reacting an alkyl halide with Na2S2O3·5H2O at 60–70 °C in DMSO.
Article
A novel, simple, one-pot procedure for the synthesis of new 7H-naphtho[1,8-ef]pyrimido[4,5-b]azocine-7,10,12,13(8H,9H,11H)-tetraones by the addition reaction of acenaphthoquinone and 6-aminouracil derivatives followed by oxidative cleavage of the corresponding intermediate product in the presence of lead(IV) acetate is reported. Clean reactions, ex...
Article
A one-pot, efficient and chemoselective procedure for the synthesis of new 3H-spiro[isobenzofuran-1,2 '-pyrrole]-3,3 '(1 ' H)-dione derivatives has been developed which involves room temperature oxidative cleavage of 3a,8b-dihydroxyindeno[1,2-b]pyrroles themselves synthesized from the reaction of ninhydrin and enaminones in 30% ethanol. A reasonabl...
Article
Full-text available
A simple, efficient procedure for the synthesis of 11-(1H-pyrrol-1-yl)-11H-indeno[1,2-b]quinoxaline and 3-(1H-pyrrol-1-yl)indolin-2-one derivatives in aqueous media is described. The condensation reaction between 4-hydroxyproline and isatin derivatives or 11H-indeno[1,2-b]quinoxalin-11-ones, using a catalytic amount of Zr(NO3)4 as a water tolerant...
Article
Full-text available
An efficient and odorless synthesis of disulfides from alkyl halides using thiourea and elemental sulfur in the presence of sodium carbonate in wet polyethylene glycol (PEG 200) at 40 °C without contamination by higher polysulfides has been developed. This procedure was then extended to preparation of disulfides from alkyl tosylates at 70 °C.
Article
Full-text available
Trifluoroacetic acid (TFA) is introduced as an effective catalyst for promotion of Biginelli reaction. 3,4-Dihydropyrimidin-2(1H)-one (-thione) derivatives (DHPMs) were simply and efficiently prepared using TFA catalyzed one-pot, three-component condensation β-dicarbonyl compounds, aldehydes and urea (thio).
Article
Full-text available
2,3-Dihydroquinazolin-4(1H)-one derivatives were synthesized via a one-pot, three component reaction of isatoic anhydride and an aromatic aldehyde with ammonium acetate or primary amine catalyzed by silica-bonded S-sulfonic acid in ethanol at 80°C. The reaction work-up is simple and the catalyst is easily separated from the products by filtration....
Article
An efficient and practical one-pot procedure for the direct chemoselective synthesis of isobenzofuran and spiro[isobenzofuran-1,2′-pyrrole] derivatives is developed via oxidative cleavage of 3a,8b-dihydroxyindeno[1,2-b]pyrrol-4-ones with Pb(OAc)4 at room temperature.
Article
Full-text available
Trifluoroacetic acid (TFA) is introduced as a commercially available, inexpensive and effective catalyst for the selective and eco-compatible synthesis of 2-aryl-1-arylmethyl-1H-1,3-benzimidazoles via condensation reaction of o-phenylenediamine derivatives and aromatic aldehydes in ethanol/water at room temperature.
Article
A novel and practical one-pot procedure is described for the preparation of several new of 3H-spiro[isobenzofuran-1,6′-pyrrolo[2,3-d]pyrimidine]-2′,3,4′,5′-tetraones based on the addition reaction of ninhydrin and 6-aminouracils followed by oxidative cleavage of their corresponding dihydroxyindenopyrrolopyrimidines.
Article
Full-text available
Silica sulfuric acid is utilized as a green, highly efficient, heterogeneous and recyclable catalyst for the preparation of β-enaminones and β-enamino esters from amines and β-dicarbonyl compounds under solvent-free conditions at 80 °C. Using this method, the title compounds are produced in high to excellent yields and in short reaction times.
Article
An efficient, simple, and green procedure for the synthesis of quinoxaline derivatives is described. The condensation of 1,2-diamines with 1,2-diketones using lithium bromide (LiBr) in H2O/EtOH as a green reaction media at room temperature affords the title compounds in high to excellent yields and in short reaction times.
Article
A novel, convenient, and practical one-pot procedure for the direct synthesis of spiroisoindoline-1,5′-oxazolidine derivatives is described via oxidative cleavage of 3a,8a-dihydroxyindeno[2,1-d]imidazole-2,8-diones with lead(IV) acetate at room temperature.
Article
Full-text available
Trisubstituted imidazoles have been synthesized in high yields in the presence of silica-bonded S-sulfonic acid as a catalyst. The reaction was carried out at 130°C under solvent-free conditions. The reaction work-up is simple and the catalyst is easily separated from the products by filtration.
Article
Full-text available
A highly efficient, simple and green procedure for the synthesis of β-enaminones and β-enamino esters is described. The reaction of aromatic and aliphatic amines with β-dicarbonyl compounds using catalytic amount of silica-supported LiHSO4 (LiHSO4/SiO2) under solvent-free conditions at 80 °C affords the title compounds in high to excellent yields a...
Article
In this study we report a novel one-pot reaction which stereoselectively affords alkyl spiro[indeno[1,2-b]quinoxaline-11,3′- pyrrolizine]-2′-carboxylates via the four-component condensation of ninhydrin, phenylenediamines, proline, and acrylic acid derivatives. The reactions were run in ethanol and completed at less than 25 min and the products wer...
Article
A novel and efficient procedure for the synthesis of new 7-pyrimidinylpyrimido[4,5-d]pyrimidinone derivatives was elaborated via the base-promoted cyclodimerization reaction of 5-[(dimethylamino)methylidene]-6-iminopyrimidine-2,4(1H,3H)-dione hydrochlorides. In an analogous manner, a 2-thioxo analog was prepared starting with the corresponding 2-th...
Article
Full-text available
An efficient method for synthesis of various tetrasubstituted imidazoles, using trifluoroacetic acid (TFA) as a catalytic support, by four-component condensation of benzil, aldehydes, amines, and ammonium acetate under microwave-irradiated, solvent-free conditions is described.
Article
Full-text available
The cycloaddition of azomethine ylides to alkenes is an important way to synthesize heterocycles containing pyrrolidine substruc-tures with high stereoselectivity. The stereoselectivity of these cycloaddition reactions is greatly enhanced if the azomethine ylide functionality is part of an N-heterocycle, thus providing a rather rigid ring template...
Article
P2O5/SiO2 (30% w/w) was applied as an efficient, heterogeneous, and reusable catalyst for the synthesis of β-enaminones. The reactions were rapidly completed at 80 °C under solvent-free conditions and products were obtained in good to excellent yields.
Article
In the context of our high-throughput organic synthesis program, we have studied the reactivity of special β-keto esters toward the Biginelli reaction. We have found that a diethyl-3-oxoglutarate reacts with one molecule of urea and one molecule of aldehyde under solvent-free conditions to give a new family of 3,4-dihydropyrimidin-2(1H)-ones in goo...
Article
Ammonium heptamolybdate tetrahydrate [(NH4)6Mo7O24.4H2O] efficiently catalyzes the condensation of aryl-1,2-diamines with 1,2-diketones in EtOH/H2O as a green media at room temperature to afford quinoxaline derivatives as biologically interesting compounds. Ease of recycling of the catalyst is one of the most advantages of the proposed method.
Article
Full-text available
A versatile and highly efficient procedure has been introduced for preparation of spiro pyridodipyrimidines during the investigation of the reaction of 1,3-dimethyl-6- aminouracil with isatin derivatives, ninhydrin, and acenaphthoquinone under classical or microwave-assisted solvent-free conditions.Key words: isatin, ninhydrin, acenaphtoquinone, 1,...
Article
Full-text available
A simple, highly efficient and green procedure for the condensation of aryl and alkyl 1,2-diamines with α-diketones in the presence of catalytic amount of oxalic acid at room temperature is described. Using this method, quinoxaline derivatives as biologically interesting compounds are produced in high to excellent yields and short reaction times.
Article
Full-text available
A microwave assisted one-pot three-component procedure was introduced for preparation of some dicyanomethylene derivatives of indenoquinoxaline and tryptanthrin under solvent free conditions.
Article
It has been found that ammonium chloride, which is a very inexpensive and readily available reagent, can efficiently catalyzed electrophilic substitution reactions of indoles. Diindolylmethanes were afforded by reaction of indoles with aldehydes and ketones under solvent-free conditions at 90°C in the presence of ammonium chloride in good to excell...
Article
A novel one-pot procedure for preparation of some new condensed pyrido[2,3-d]pyrimidine(1H,3H)-2,4-diones based on condensation of ninhydrin, alkyl cyanoacetate, and 6-aminouracil derivatives has been reported. The reactions were carried out in refluxed ethanol and were completed in less than 2 h. © 2007 Wiley Periodicals, Inc. Heteroatom Chem 18:1...
Article
Silica sulfuric acid catalyzed efficiently the electrophilic substitution reaction of an indoles with various isatins in dicholoro methane to afford the corresponding oxindoles derivatives in high yields under r.t. The catalyst exhibited remarkable reusable activity.
Article
An efficient synthesis of various tetrasubstituted imidazoles using silica gel-supported sodium bisulfate as a catalytic support by four-component condensation of benzil or benzoin, aldehydes, amines, and ammonium acetate under microwave irradiation or classical heating conditions is described.
Article
A series of ninhydrin derived α-acyloxycarboxamide derivatives were synthesized in good yields in a Passerini three-component reaction by condensation of ninhydrin, carboxylic acids, and isocyanides.
Article
3,4-Dihydropyrimidin-2(1H)-ones derivatives were synthesized in moderate to high yields in one-pot three component reaction from the corresponding aldehydes, ketones or 1,3-dicarbonyl compounds and urea, in the presence of catalytic amount of KAl(SO4)2·12H2O (Alum) supported on silica gel (Alum-SiO2) as a non-toxic, reusable, inexpensive and easily...
Article
11H-Indeno[1,2-b]quinoxalin-11-ones generated in situ from ninhydrin and various 1,2-phenylenediamines, catalysed by montmorillonite K10 under microwave irradiation, condense with 4-hydroxyproline to produce 11-(1H-pyrrol-1-yl)-11H-indeno[1,2-b]quinoxaline derivatives in good yields.
Article
Facile reaction involving 4-hydroxy proline and activated carbonyl compounds such as 11H-indeno[l,2-b]quinoxalin-l 1-one and isatin derivatives catalyzed by silica sulfuric acid under microwave irradiation yielding some novel 11-(1H-pyrrol-l-yl)-l H-indeno[l,2-b]quinoxaline and 3-(1H-pyrrol-1-yl)indolin-2-one derivatives are described.
Article
In this study, we introduced a very simple, one-pot and green methodology for preparation of polysubstituted furans by reaction of aromatic aldehydes, DMAD, and alkylisocyanides in water and at room temperature. © 2005 Wiley Periodicals, Inc. 16:259–262, 2005; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20086
Article
Facile reaction involving 4-hydroxy proline and activated carbonyl compounds such as 11H-indeno[1,2-blquinoxalin-11-one and isatin derivatives catalyzed by silica sulfuric acid under microwave irradiation yielding some novel 11-(1H-pyrrol-1-yl)-11Hindeno[1,2-b]quinoxaline and 3-(1H-pyrrol-1-yl)indolin-2-one derivatives are described.
Article
[reaction: see text] 11-(1H-Pyrrol-1-yl)-11H-indeno[1,2-b]quinoxaline and 3-(1H-pyrrol-1-yl)indolin-2-one derivatives have been synthesized in good yields in a novel, one-pot, and efficient process by condensation of 11H-indeno[1,2-b]quinoxalin-11-one or isatin derivatives with 4-hydroxyproline on solid-support montmorillonite K10 under microwave i...
Article
With regard to green chemistry, atom-efficient transformations of easily available starting materials into complex organic building blocks become increasingly important. Here, a novel four-component condensation of ninhydrin, 1,2-phenylene diamine, proline and N-aryl maleimides to some new spiro pyrrolizidines via 1,3-dipolar cycloadditions of azom...
Article
KAl(SO(4))(2).12H(2)O is found to catalyze efficiently the stereoselective one-pot three-component cyclocondensation of homophthalic anhydride, aldehydes, and amines under mild conditions to afford the corresponding cis-isoquinolonic acids in good yields.
Article
We introduced a very simple, one-pot three component procedure for preparation of alkyl indeno[1,2-b]quinoxalin-11-ylideneacetates 4 from reaction of ninhydrin 1, phenylenediamines 2, (alkoxycarbonylmethyl)triphenylphosphonium bromides 3, and sodium acetate in water and under solvent-free conditions. © 2005 Wiley Periodicals, Inc. Heteroatom Chem 1...