Synthesis Of New Pyrimido Research Articles

Fe3O4‐SAHPG‐Pd0 nanoparticles: A ligand‐free and low Pd loading quasiheterogeneous catalyst active for mild Suzuki–Miyaura coupling and CH activation of pyrimidine cores

This paper reports a green magnetic quasiheterogeneous efficient palladium catalyst in which Pd0 nanoparticles have been immobilized in self‐assembled hyperbranched polyglycidole (SAHPG)‐coated magnetic Fe3O4 nanoparticles (Fe3O4‐SAHPG‐Pd0). This catalyst has been used for effective ligandless Pd catalyzed Suzuki–Miyaura coupling reactions of different aryl halides with substituted boronic acids at room temperature and in aqueous media. Herein, SAHPG is used as support; it also acts as a reducing agent and stabilizer to promote the transformation of PdII to Pd0 nanoparticles. Also, this environmental friendly quasiheterogeneous catalyst is employed for the first time in the synthesis of new pyrimido[4,5‐b]indoles via oxidative addition/CH activation reactions on the pyrimidine rings, which were obtained with higher yield and faster than when Pd(OAc)2 was used as the catalyst. Interestingly, the above‐mentioned catalyst could be recovered in a facile manner from the reaction mixture by applying an external magnet device and recycled several times with no significant decrease in the catalytic activity.

SBA-15/PrN(CH2PO3H2)2 as a novel and efficient mesoporous solid acid catalyst with phosphorous acid tags and its application on the synthesis of new pyrimido[4,5-b]quinolones and pyrido[2,3-d]pyrimidines via anomeric based oxidation

Abstract In this work, SBA-15/PrN(CH2PO3H)2 as a novel and heterogeneous catalyst containing of phosphorous acid groups was fully characterized by using various analysis techniques. A good range of novel pyrido[2,3-d]pyrimidines and pyrimido[4,5-b]quinolines were synthesized in the presence of SBA-15/PrN(CH2PO3H)2 under solvent-free condition. The major advantages of the described method are high yields, short reaction times and reusability of the catalyst. The obtained results from this research will be supported by the idea of rational designs, syntheses and applications of task-specific catalysts and molecules for the development of biomimetic anomeric based oxidation and/or aromatization mechanism.

Efficient synthesis, reactions, and biological activities of new thieno and furopyrazolo[3,4‐b]pyrazines and their related heterocycles

AbstractIn the present investigation, a simple and straightforward methodology for the preparation of novel bifunctional thienopyrazolopyrazines 4a–d has been reported. Synthesis of thieno or furopyrazolopyrazines 5a,b,e,f was achieved by the reaction of o‐amino‐esters 4a,b,e,f with 2,5‐dimethoxytetrahydrofuran. The latter pyrrolyl derivatives 5a,b,e,f were used as starting intermediates for the synthesis of new pyrimido, pyrido, and pyrazino heterocycles fused to the thieno or furopyrazolopyrazine moiety. Furthermore, alkaline hydrolysis of the o‐amino‐ester 4a followed by acidification afforded the corresponding o‐amino carboxylic acid 15, which was used as a versatile precursor for the synthesis of other heterocyclic compounds fused to the thienopyrazolopyrazine ring system, namely: pyrimidine, oxazine, oxazepine, and pyridine derivatives 16–23. The chemical structures of the synthesized compounds were confirmed on the basis of elemental and spectral analyses (Fourier‐transform infrared spectroscopy [FT‐IR], 1H nuclear magnetic resonance [NMR], and mass spectroscopy [MS] in addition to 13C NMR for some of them). Moreover, from the biological screening, we found that most of the tested compounds exhibited promising antifungal, antibacterial, and anti‐inflammatory activities compared with the corresponding reference drugs.

Design, two-directional synthesis, DFT study of new pyrimido[5,4-d]pyrimidine-2,8-dione derivatives

A facile two-directional synthesis of new pyrimido[5,4-d]pyrimidine-2,8-dione was reported via an efficient reaction of premade bis-aldehydes and 1-(2-amino-1,2-dicyanovinyl)-3-phenylurea in the presence of triethylamine as the base and Cu (II) as catalyst. As there is controversy about the formation of two types of products, that is, purine or pyrimidine ring containing compounds in the reaction of diaminomaleonitrile with isocyanates and aldehydes, the computational model chemistry has been employed to obtain new insight about this reaction and determining the dominant pathway of the process. Using DFT model, two alternative pathways have been explored and geometrical isomerization of central double bond has been considered. Accordingly, the evaluated energy barriers affirm the formation of six-membered pyrimidine ring as the major product in the presence of CuCl2 as the catalyst and MeOH as solvent.

Regioselective synthesis of new 5-methyl-5H-pyrimido[4′,5′:4,5][1,3]thiazino [3,2-a]perimidines

ABSTRACTA convenient and efficient regioselective synthesis of new pyrimido[4′,5′:4,5] [1,3]thiazino[3,2-a]perimidines is described through intermolecular heterocyclization of 2,4-dichloro-5-(chloromethyl)-6-methylpyrimidine and 1H-perimidine-2(3H)-thione in short reaction times under mild conditions.

Synthesis and Antiproliferative Evaluation of New Pyrimido[1,6‐a]Thieno[2,3‐d]Pyrimidine Derivatives

A facile one‐pot synthesis of new pyrimido[1,6‐a]thieno[2,3‐d]pyrimidin‐4‐ones 3a ,3b is reported via base‐catalyzed reaction of 2‐amino‐3‐cyanothiophenes 1a ,1b with 2,4‐dichloro‐5‐bromo‐6‐methylpyrimidine 2. Subsequent treatment of the products with several amines under a mild condition gave a host of the new amino derivatives 4a, 4b, 4c, 4d, 4e, 4f, 4g, 4h, 4i, 4j, 4k, 4l. The target compounds were evaluated for antiproliferative activity by an 3‐(4, 5‐dimethylthiazol‐2‐yl)‐2,5‐diphenyl tetrazolium assay on human breast cancer (MCF‐7) and mouse fibroblast nonmalignant (L929) cell lines. The activation was structural, concentration, and time dependent. Doses inducing 50% cell‐growth inhibition (IC50) for compounds 3a ,3b and 4a, 4b, 4c, 4d, 4e, 4f, 4g, 4h, 4i, 4j, 4k, 4l against MCF‐7 cells were explored. Compounds 4f and 4l as the two most potent analogs induced a sub‐G1 peak in the flow‐cytometry histogram of treated cells, compared with control, indicating that apoptotic cell death is involved in compound 4f‐induced and compound 4l‐induced toxicity. Compounds 4f and 4l exerted cytotoxic and proapototic effects on MCF‐7 cell line.

Synthesis of new pyrimido[4,5-d]pyrimidine derivatives from 5-acetyl-6-methyl-4-methylsulfanylpyrimidine-2(1H)-thiones and guanidine

Reactions of 5-acetyl-1-aryl(alkyl)-6-methyl-4-methylsulfanylpyrimidine-2(1H)-thiones (prepared from diacetylketene N,S-acetal) with guanidine afforded 3-alkyl- and 3-aryl-7-amino-5-methyl-4-methylidene-3,4-dihydropyrimido[4,5-d]pyrimidine-2(1H)-thiones. By-products of these reactions (5-acetyl-1-alkyl(aryl)-6-methyl-2-thiouracils) can also be obtained from the starting pyrimidinethiones and EtONa in EtOH. Pyrimidopyrimidinethiones can react with MeOH at the methylidene group in the presence of MeONa.

Convenient synthesis of new pyrimido[4,5-e][1,3,4]thiadiazine derivatives

New 3-alkylsulfanyl-7-chloro-5-methyl-1-phenyl-1H-pyrimido[4,5-e][1,3,4]thiadiazines were synthesized via the cyclocondensation of alkyl-2-phenylhydrazinecarbodithioates with 5-bromo-2,4-dichloro-6-methylpyrimidine in basic acetonitrile.

Microwave-assisted synthesis of new pyrimido[4′,5′:4,5]thiazolo[3,2- a] benzimidazol-4(3 H)-one derivatives in solvent-free condition

Microwave-assisted synthesis of new 2-arylpyrimido[4′,5′:4,5]thiazolo[3,2- a]benzimidazol-4(3 H)-ones from 3-aminothiazolo[3,2- a]benzimidazol-2-carboxamide and aroyl halides in solvent-free condition is described. In comparison with classical conditions the reactions are faster and the yields are higher under microwave irradiation.

Synthesis of Some NewPyrimido[5,4-a]Indolizines

The synthesis of new pyrimido[5,4-a]indolizines by reaction of 2-aminoindolizine-1-carbonitrile or ethyl 2-aminoindolizine-1-carboxylate with various electrophilic reagents is described. The structure of the products was confirmed by their elemental analysis and IR, 1H NMR, and mass spectra. The results of a preliminary antimicrobial screening are also presented.

SYNTHESIS OF NEW CONDENSED PYRIMIDO (1,6-a) INDOLE OF POTENTIAL PHARMACOLOGICAL INTREST

Triethyloxonium tetrafluoroborate has been used as a selective o-alkalyting agent of lactam for preparation of the lactim ether of oxindole. The synthesis of new pyrimido 1,6 -a indole derivatives is described. Addition of dicyanomethylidene indole (1) to varicous fluorophenyl isothiocyanates gave 2- fluorophenyl -3- imino -1- thioxo -1,2,3,5-tetrahydropyrimido, 1,6-a) indole -4- carbonitrile (2). Reduction of these compounds with sodium borohydride gave the corresponding enaminonitriles 3- amino -2- fluorophenyl1-thioxo -1,2,4a , 50 tetrahydropyrimido 1,6-a indole -4 carbonitrile (3) . Treatment of enaminonitriles with chloracetyl chloride afforded the N- chloroacetylamino derivatives (4) which underwent cyclization either by acid or base to the tetracyclic compounds 3- chloromethyl (or alkylaminomethyl) -1- oxo-6- thioxo-12-12a - dihydro-[ 2H,5H ]- pyrimido [4, 5, 4, 5] pyrimido[ 1, 6-a) indoles (5). Preliminary pharmacological screening of some compounds revealed analgesic and anti-inflammatory activities.

ChemInform Abstract: Lactam Acetals and Acid Amide Acetals. Part 54. New Synthesis of Pyrimido(4,5‐f)pyrrolizines (IV), (VII).

ChemInformVolume 20, Issue 52 Heterocyclic Compounds ChemInform Abstract: Lactam Acetals and Acid Amide Acetals. Part 54. New Synthesis of Pyrimido(4,5-f)pyrrolizines (IV), (VII). A. V. KADUSHKIN, VNI khim.-farm. inst. im. Ordzhonikidze, Moskva 119815Search for more papers by this authorT. V. GOLOVKO, VNI khim.-farm. inst. im. Ordzhonikidze, Moskva 119815Search for more papers by this authorV. G. GRANIK, VNI khim.-farm. inst. im. Ordzhonikidze, Moskva 119815Search for more papers by this author A. V. KADUSHKIN, VNI khim.-farm. inst. im. Ordzhonikidze, Moskva 119815Search for more papers by this authorT. V. GOLOVKO, VNI khim.-farm. inst. im. Ordzhonikidze, Moskva 119815Search for more papers by this authorV. G. GRANIK, VNI khim.-farm. inst. im. Ordzhonikidze, Moskva 119815Search for more papers by this author First published: December 26, 1989 https://doi.org/10.1002/chin.198952205AboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onEmailFacebookTwitterLinked InRedditWechat No abstract is available for this article. Volume20, Issue52December 26, 1989 RelatedInformation

A New Synthesis of Pyrimido[6,1-a]isoquinoline Derivatives and Related Compounds

Synthese des composes du titre a partir de [benzyl-1' aryl-2″ ethyl-3' ureido]-3 propionates d'ethyle; application a la synthese de derives d'isoquino [2,1-c] et quinazolines, de thieno [3',2':3,4]- et -[2',3':3,4] pyrido [1,2-c] quinazolines, de pyrimido [6,1-a] isoquinoleines et de thieno [3',2':3,4] pyrido [1,2-c] pyrimidines

A new synthesis of pyrimido[5,4‐e]‐as‐triazine 4‐oxides and their ring transformation to pyrrolo[3,2‐d]pyrimidines

AbstractA new synthesis of certain pyrimido[5,4‐e]‐as‐triazine 4‐oxides and their ring transformation to pyrrolo‐[3,2‐d]pyrimidines by the 1,3‐dipolar cycloaddition reaction is described. Thus, reaction of 6‐hydrazino‐1,3‐dimethyluracil (1) with triethyl orthoformate gave 6‐ethoxymethylenehydrazino‐1,3‐dimethyluracil (2). Treatment of 2 with arylamines gave 6‐arylaminomethylenehydrazino‐1,3‐dimethyluracils (3a‐e). Nitrosative cyclization of 3a‐e with sodium nitrite afforded 3‐arylaminofervenulin 4‐oxides (6a‐e). Reaction of 6a‐e with acetylenic esters yielded 7‐alkoxycarbonyl‐6‐arylamino‐1,3‐dimethylpyrrolo[3,2‐d]pyrimidine‐2,4(1H,3H‐diones (15a‐e and 16).

A New Synthesis of Pyrimido[4,5-b]quinoline-2,4-(1H,3H)-diones by Reaction of 6-Arylamino-1,3-dimethyluracils with Carbon Disufide

A New Synthesis of Pyrimido[4,5-b]quinoline-2,4-(1H,3H)-diones by Reaction of 6-Arylamino-1,3-dimethyluracils with Carbon Disufide

A new synthesis of pyrimido[4,5-b]quinoline-2,4(1H,3H)diones (5-deazaalloxazines) by oxidative cyclization of aryl-bis(6-amino-1,3-dimethyluracil-5-yl)-methanes with diethyl azodicarboxyle.

Treatment of aryl-bis (6-amino-1, 3-dimethyluracil-5-yl) methanes, which were prepared by the condensation of 6-amino-1, 3-dimethyluracil with aryl aldehydes, with diethyl azodicarboxylate in the presence of sulfolane led to the formation of the corresponding 1, 3-dimethylpyrimido [4, 5-b] quinoline-2, 4 (1H, 3H) diones (1, 3-dimethyl-5-deazaalloxazines).

ChemInform Abstract: A NEW SYNTHESIS OF PYRIMIDO(4,5‐B)QUINOLINE‐2,4(1H,3H)‐DIONE (5‐DEAZAALLOXAZINE) DERIVATIVES

Chemischer InformationsdienstVolume 9, Issue 4 Heterocyclic Compounds ChemInform Abstract: A NEW SYNTHESIS OF PYRIMIDO(4,5-B)QUINOLINE-2,4(1H,3H)-DIONE (5-DEAZAALLOXAZINE) DERIVATIVES K. SENGA, K. SENGASearch for more papers by this authorK. SHIMIZU, K. SHIMIZUSearch for more papers by this authorS. NISHIGAKI, S. NISHIGAKISearch for more papers by this authorF. YONEDA, F. YONEDASearch for more papers by this author K. SENGA, K. SENGASearch for more papers by this authorK. SHIMIZU, K. SHIMIZUSearch for more papers by this authorS. NISHIGAKI, S. NISHIGAKISearch for more papers by this authorF. YONEDA, F. YONEDASearch for more papers by this author First published: January 24, 1978 https://doi.org/10.1002/chin.197804245AboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinked InRedditWechat No abstract is available for this article. Volume9, Issue4January 24, 1978 RelatedInformation

New Synthesis of Pyrimido[5,4-e]-as-triazines by the Reaction of 6-Hydrazino-1,3-dimethyl-5-nitrosouracil with Benzylidenetriphenylphosphoranes

New Synthesis of Pyrimido[5,4-e]-as-triazines by the Reaction of 6-Hydrazino-1,3-dimethyl-5-nitrosouracil with Benzylidenetriphenylphosphoranes

A new synthesis of pyrimido[4,5-e]-as-triazine 4-oxides by nitrosative cyclization of aldehyde uracil-6-ylhydrazones in the presence of diethyl azodiformate

The nitrosative cyclization of the aldehyde uracil-6-ylhydrazones in the presence of diethyl azodiformate gives the corresponding pyrimido[5,4-e]-as-triazine 4-oxides; several toxoflavin and fervenulin 4-oxides were prepared by this method. The compounds showed characteristic u.v. spectra.

A New Synthesis of Pyrimido[4,5-e][1,2,4]triazines from 5,5-Dibromopyrimidines

Abstract A new method for the synthesis of pyrimido-[4,5-e][1,2,4]triazines from 5,5-dibromopyrimidines was studied. Condensation of dibromopyrimidines (1a, b) with aminoguanidine or its analogues gave the 6,8-dioxo series (5) of the pyrimidotriazine, and aminodibromopyrimidines (2a, b) gave the 6-amino-8-oxo series (6).