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Journal articles on the topic '3-d]pyrimidine-4-one'

Author: Grafiati

Published: 5 June 2025

Last updated: 2 August 2025

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1

Otero, Iran, Holger Feist, Dirk Michalik, Manfred Michalik, José Quincoces та Klaus Peseke. "Synthesis of Iso-C-nucleoside Analogues from 1-(Methyl 2-O-benzyl-4,6- O-benzylidene-3-deoxy-α-D-altropyranosid-3-yl)but-3-yn-2-ones". Zeitschrift für Naturforschung B 60, № 11 (2005): 1175–85. http://dx.doi.org/10.1515/znb-2005-1110.

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1-(Methyl 2-O-benzyl-4,6-O-benzylidene-3-deoxy-α-D-altropyranosid-3-yl)but-3-yn-2-one (3a) reacted with 3-amino-1H-1,2,4-triazole and 5-aminopyrazole-4-carboxylic acid derivatives in the presence of base to furnish the triazolo[1,5-a]pyrimidine (5) and the pyrazolo[1,5- a]pyrimidines (8a - d), respectively. Treatment of 1-(methyl 2-O-benzyl-4,6-O-benzylidene-3- deoxy-α-D-altropyranosid-3-yl)-4-phenyl-but-3-yn-2-one (3b) with cyanacetamide, 2-cyano-N- (4-methoxyphenyl)acetamide und N-aryl-3-oxo-butyramides afforded the substituted nicotinonitriles (11a - d). Furthermore, reaction of 3b with 2-b

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2

Tank, Manishkumar Jinabhai, Navinkumar A. Kucha, Chirag G. Naik, Tina R. Barot, and G. M. Malik. "Adamantane-pyrido[2,3-d]pyrimidine Derivatives; Synthesis, Characterization and Investigation of Antimicrobial Study." Oriental Journal Of Chemistry 39, no. 2 (2023): 393–402. http://dx.doi.org/10.13005/ojc/390219.

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Target molecules based on Adamantane-pyrido[2,3-d]pyrimidine derivatives were prepared. Adamantane-pyrido[2,3-d]pyrimidine series using N-(hydroxyadamantan-1-yl)-5-(2,4-substitutedphenyl)-2-Methyl-4-Oxo-7-(2-oxo-2H-Chromen-3-yl)pyrido[2,3-d]Pyrimidine-3(4H)carboxamide (6a-j) was synthesized by reaction between 3-(2-chloroacetyl)-5-(2,4-substitutedphenyl)-2-Methyl-7-(2-Oxo-2H-Chromen-3-yl) pyrido[2,3-d]pyrimidin-4(3H)-one (5a-j) and 3-aminoadamantan-1-ol. These derivatives of Adamantane-pyrido[2,3-d]Pyrimidine were investigated in vitro for their biological characteristics against the strains w

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3

Dabaeva, V. V., M. R. Baghdasaryan, I. M. Barkhudaryants, E. G. Paronikyan, and Sh Sh Dashyan. "Synthesis of new fused 3(4)-substituted 11-furylthieno[3,2-<i>d</i>]pyrimidine derivatives." Журнал общей химии 93, no. 9 (2023): 1351–57. http://dx.doi.org/10.31857/s0044460x23090056.

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A method was developed for the synthesis of new fused 3-alkyl-substituted derivatives of thieno[3,2- d ]pyrimidin-4(3 H )-ones based on 11-(2-furyl)-8,8-dimethyl-7,10-dihydro-8 H -pyrano[3′′,4′′:5′,6′]pyrido[3′,2′:4,5]-thieno[3,2- d ]pyrimidin-4(3 H )-one via nucleophilic substitution in the pyrimidine ring. A series of fused 4-amino-substituted 11-furylthieno[3,2- d ]pyrimidine derivatives was also synthesized from the corresponding 4-chloro derivative.

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4

Hossain, M. I., and M. M. H. Bhuiyan. "Synthesis and Antimicrobial Activities of Some New Thieno and Furopyrimidine Derivatives." Journal of Scientific Research 1, no. 2 (2009): 317–25. http://dx.doi.org/10.3329/jsr.v1i2.2299.

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Fused pyrimidines, 8,9-dimethyl[1,2,4]triazolo[4,3-c]thieno[3,2-e]pyrimidine 5, 3,8,9-trimethyl[1,2,4]triazolo[4,3-c]thieno[3,2-e]pyrimidine 6, 4-benzylidinehydrazono-5,6 dimethylthieno[2,3-d]pyrimidine 7, 4-[4/-hydroxybenzylidine]hydrazono-5,6-dimethylthi-eno[2,3-d]pyrimidine 8, 4-[4/-tolylidin]hydrazono-5,6-dimethylthieno[2,3-d]pyrimidine 9, 4-[4/-nitrobenzylidine]hydrazono-5-ethyl-6-methylthieno[2,3-d]pyrimidine 10 and 4-[4/-chlorobenzylidine]hydrazono-5-ethyl-6-methylthieno[2,3-d]pyrimidine 11 are prepared in good yield by an initial treatment of 2-amino-4,5-dimethylthiophene-3-carbonitril

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5

Tiwari, Sangeeta, Ashok K. Yadav, and A. K. Mishra. "Some New Pyrido[2,3-d]pyridimines and their Nucleoside of Biological Importance." E-Journal of Chemistry 7, s1 (2010): S85—S92. http://dx.doi.org/10.1155/2010/812567.

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Chalcones (I) reacted with malanonitrile and ammonium acetate yielded 2-amino-3-cyano-4,6-disubstituted pyridines (II) in excellent yield. 4-Amino-5,7-disubstituted pyrido [2,3-d]pyrimidine-2(1H)-thiones (III), 4-amino-5,7-disubstituted pyrido[2,3-d]pyrimidines (IV) and 4-imino-3,5,7-trisubstituted pyrido[2,3-d]pyrimidin-2(1H)-ones (V) have been synthesized by the condensation of compound (II) with thiourea, formamide and arylisocynate respectively. The ribofuranosidesviz. 4-amino-5,7-disubstituted-1- [2',3',5'-tri-o-benzoyl-β,D-ribofuranosyl]pyrido[2,3-d]pyrimidine-2-(1H)-thiones (VI) and 4-i

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6

Hafez, Hend N., and Abdel-Rhman B. A. El-Gazzar. "Synthesis and evaluation of antitumor activity of new 4-substituted thieno[3,2-d]pyrimidine and thienotriazolopyrimidine derivatives." Acta Pharmaceutica 67, no. 4 (2017): 527–42. http://dx.doi.org/10.1515/acph-2017-0039.

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Abstract 3-Methyl-6-phenyl-2-thioxo-2,3-dihydrothieno[3,2-d]pyrimidin- 4(1H)-one (2), on treatment with phosphorous oxychoride, affored 4-chloro-3-methyl-6-phenyl -thieno[3,2-d]pyrimidine- 2(3H)-thione (3). A series of novel 6-phenyl-thieno[3,2-d]pyrimidine derivatives 4-9 bearing different functional groups were synthesized via treatment of compound 3 with different reagents. On the other hand, compound 2 was used to synthesize ethyl-[(3-methyl-6-phenyl-2-thioxo-2,3-dihydrothieno[ 3,2-d]pyrimidin-4-yl)-oxy]acetate (10), 2-hydrazinyl- -3-methyl-6-phenyl-thieno[3,2-d]pyrimidin-4(3H)-one (11), 3

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7

Tang, Chu, Yongju Liang, Shun Bai, et al. "Synthesis and antiproliferative evaluation of novel tetrahydrobenzo[4′,5′]thieno[3′,2′:5,6]pyrido[4,3-d]pyrimidine derivatives." RSC Adv. 4, no. 55 (2014): 29187–92. http://dx.doi.org/10.1039/c4ra03535f.

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8

Youssef, Ahmed Said Ahmed. "Reactions of 2-amino-4,5,6,7-tetrahydro[1]benzothiophene-3-carbonitrile and 6-amino-1,4-dihydro-3-methyl-1,4-diphenylpyrano[2,3-c]pyrazole-5-carbonitrile with substituted benzylidenemalononitriles, α,β-acetylenic esters and ketones". Journal of Chemical Research 2009, № 4 (2009): 214–17. http://dx.doi.org/10.3184/030823409x435874.

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Reactions of 2-amino-4,5,6,7-tetrahydro[1]benzothiophene-3-carbonitrile (1a) with substituted benzylidenemalononitriles gave 4-amino-2-(1-cyano-2-arylvinyl)benzothieno[2,3- d]pyrimidine derivatives (3) as ( E,Z)-mixtures and in one case (2c) as separated ( Z)- and ( E)-isomers. Similar treatment of 6-amino-1,4-dihydro-3-methyl-1,4-diphenyl-pyrano[2,3- c]pyrazole-5-carbonitrile (4) yielded similarly-formed pyrazolopyranopyrimidine derivatives (5a, b) as ( Z)-and ( E)-stereoisomers. Attempted acetylation of the aminobenzothienopyrimidines resulted in degradation of the pyrimidine ring and the fo

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9

Avasthi, Kamlakar, Lakshmi Shukla, Ruchir Kant, and Krishnan Ravikumar. "Folded conformations due to arene interactions in dissymmetric and symmetric butylidene-linker models based on pyrazolo[3,4-d]pyrimidine, purine and 7-deazapurine." Acta Crystallographica Section C Structural Chemistry 70, no. 6 (2014): 555–61. http://dx.doi.org/10.1107/s2053229614009449.

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The butylidene-linker models 1-[2-(2,6-dimethylsulfanyl-9H-purin-9-yl)-2-methylidenepropyl]-4,6-bis(methylsulfanyl)-1H-pyrazolo[3,4-d]pyrimidine, C18H20N8S4, (XI), 7,7′-(2-methylidenepropane-1,3-diyl)bis[3-methyl-2-methylsulfanyl-3H-pyrrolo[2,3-d]pyrimidin-4(7H)-one], C20H22N6O2S2, (XIV), and 7-[2-(4,6-dimethylsulfanyl-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-2-methylidenepropyl]-3-methyl-2-methylsulfanyl-3H-pyrrolo[2,3-d]pyrimidin-4(7H)-one, C19H21N7OS3, (XV), show folded conformations in solution, as shown by1H NMR analysis. This folding carries over to the crystalline state. Intramolecular π–π int

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10

Kumar, B. S., P. V. A. Lakshmi, B. S. Veena, and E. Sujatha. "Synthesis and antibacterial activity of novel pyrano[2,3-d]pyrimidine-4-one–3-phenylisoxazole hybrids." Russian Journal of General Chemistry 87, no. 4 (2017): 829–36. http://dx.doi.org/10.1134/s1070363217040260.

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11

Yin, Xuelian, and Yang-Heon Song. "5-Methyl-1-phenyl-3-(thieno[2,3-d]pyrimidin-4-yl)chromeno[4,3-d]pyrazolo[3,4-b]pyridin-6(3H)-one." Molbank 2022, no. 4 (2022): M1469. http://dx.doi.org/10.3390/m1469.

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A chromeno[4,3-d]pyrazolo[3,4-b]pyridinone derivative 3 bearing thieno[2,3-d]pyrimidine moiety, 5-methyl-1-phenyl-3-(thieno[2,3-d]pyrimidin-4-yl)chromeno[4,3-d]pyrazolo[3,4-b]pyridin-6(3H)-one, was efficiently prepared in 75% yield by the reaction of 3-phenyl-1-(thieno[2,3-d]pyrimidin-4-yl)-1H-pyrazol-5-amine 1 with 3-acetyl-2H-chromen-2-one 2 in the presence of FeCl3-SiO2 as a catalyst in refluxing ethanol for 6 h. The structure of the new synthesized compound was characterized by 1H-, 13C- NMR, IR spectroscopy, mass-spectrometry, and elemental analysis.

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12

Hafez, Hend N., Abdel-Rhman B. A. El-Gazzar, and Magdi E. A. Zaki. "Simple approach to thieno[3,2-d]pyrimidines as new scaffolds of antimicrobial activities." Acta Pharmaceutica 66, no. 3 (2016): 331–51. http://dx.doi.org/10.1515/acph-2016-0029.

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Abstract 6ʹ-(4-Chlorophenyl)-spiro[cyclohexane-1,2ʹ-thieno[3,2-d][1,3] oxazin]-4ʹ(1ʹH)-one (1) was synthesized and used as a starting material for the synthesis of a novel series of spiro compounds having biologically active sulfonamide 2a-e and 3ʹ-(4-acetylphenyl)-6ʹ- (4-chlorophenyl)-1ʹH-spiro[cyclohexane-1,2ʹ-thieno[3,2-d] pyrimidine-4ʹ(3ʹH)-one (3). Compound 2a was used as a key intermediate for the synthesis of sulfonyl carbothioamide derivatives 4a-c. Also, compound 3 was used as an intermediate for the synthesis of 3ʹH-spiro[cyclohexane-1,2ʹ-thieno[3,2-d]pyrimidin]-3ʹ-yl] phenyl}-2-imin

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13

Abdelhamid, Abdou O., Zeineb H. Ismail, and Anhar Abdel-Aziem. "Reactions with Hydrazonoyl Halides 601: Synthesis of Thieno[2′,3′:4,5] Pyrimidino[1,2-b][1,2,4,5]tetrazines, [1]benzothieno[2′,3′:4,5]pyrimidino [1,2-b][1,2,4,5]tetrazines, Pyrazolo[3′,4′:4,5]pyrimidino[1,2-b] [1,2,4,5]tetrazines and Pyrazolo[3,4-d]pyridazines." Journal of Chemical Research 2007, no. 10 (2007): 609–16. http://dx.doi.org/10.3184/030823407x256118.

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Thieno[2′,3′:4,5]pyrimidino[1,2- b][1,2,4,5]tetrazine, [1]benzothieno-[2′,3′:4,5]pyrimidino[1,2- b][1,2,4,5]tetrazine, pyrazolo [3′,4′:4,5]pyrimidino[1,2- b][1,2,4,5]tetrazine, triazolo[4,3- a]pyrimidin-5(1 H)-one, 1-{[2-(1-benzofuran-2-yl)-5-phenyl-4,5-dihydro-1 H-pyrazol-1-yl]-4-substituted-1,3-thiazol-5-yl}-2-phenyldiazene, 3-acyl-4-(1-benzofuran-2-ylcarbonyl) pyrazole and pyrazolo[3,4- d]pyridazine derivatives could be obtained via reactions of hydrazonoyl halides with the appropriate pyrimidine-2-thione, 3-amino-5,6-dimethyl-2-sulfanylthieno[2,3- d]pyrimidin-4(3 H)-one, 5-amino-6-mercapto

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14

Mordovina, N. I., O. V. Kovalchukova, B. E. Zaitsev, et al. "Complexes of d and f Metals with 2-Methyl-3-hydroxy(amino)pyrido[1,2-a]pyrimidine-4-one. Crystal Structure of 2-Methyl-3-hydroxypyrido[1,2-a]pyrimidine-4-one." Russian Journal of Coordination Chemistry 29, no. 12 (2003): 880–85. http://dx.doi.org/10.1023/b:ruco.0000008402.21557.58.

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15

Choura, Emna, Fares Elghali, Paul J. Bernard, et al. "Benzochromenopyrimidines: Synthesis, Antiproliferative Activity against Colorectal Cancer and Physicochemical Properties." Molecules 27, no. 22 (2022): 7878. http://dx.doi.org/10.3390/molecules27227878.

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Ten new differently substituted 3-benzyl-5-aryl-3,5-dihydro-4H-benzo[6,7]chromeno[2,3-d]pyrimidin-4,6,11-triones 3 were synthesized by a simple and cost-efficient procedure in a one-pot, three-component reaction from readily available ethyl 2-amino-4-aryl-5,10-dioxo-5,10-dihydro-4H-benzo[g]chromene-3-carboxylates, benzylamine and triethyl orthoformate under solvent- and catalyst-free conditions. All the new compounds were screened for their antiproliferative activity against two colorectal-cancer-cell lines. The results showed that the compounds 3-benzyl-5-phenyl-3,5-dihydro-4H-benzo[6,7]chrom

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16

Pragnesh, B. Rana, A. Patel Jigisha, D. Mistry B., and R. Desai K. "Synthesis of various pharma based pyrido[2,3-d]pyrimidine as well as pyrido[1,2-a]pyrimidine and their antimicrobial activities." Journal of Indian Chemical Society Vol. 87, Mar 2010 (2010): 365–72. https://doi.org/10.5281/zenodo.5779153.

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Department of Chemistry, B. K. M. Science College, Valsad-396 001, Gujarat, India <em>E-mail :</em> bhavana_mistryll@yahoo.co.in <em>Manuscript received 27 October 2008, revised 2 April 2009, accepted 7 August 2009</em> 4-Amino-7-{ 4'-[(4" -methylplperazlnyl)dlazenyl)phenyi}-5-(snbstitutedphenyl)-1<em>H</em>-pyrldo[2,3-d]pyrimldine-2-one (4a-j), 4-amino-7-{4'-[(4"-methylpiperazinyl)diazenyl]phenyi}-5-(substitutedphenyl)-1H-pyrldo[2,3-d]pyrlmldhle-2-thlone (5a-j), 4-thioureido-7-{ if -[(4" -methylpiperazinyl)dlazenyl)phenyl}-5-(substitutedphenyl)-1<em>H</em>-pyrldo[2,3-d]

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17

Hayat, Faisal, Attar Salahuddin, and Amir Azam. "Synthesis, characterization, antiamoebic activity and cytotoxicity of new pyrazolo[3, 4-d]pyrimidine-6-one derivatives." Journal of Enzyme Inhibition and Medicinal Chemistry 26, no. 4 (2010): 472–79. http://dx.doi.org/10.3109/14756366.2010.528414.

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18

Firoozpour, Loghman, Hoda Yahyavi, Ramona Ejtemaei, Setareh Moghimi, and Alireza Foroumadi. "A One-Pot, Three-Component, Solvent-Free Synthesis of Novel 6H-Chromeno[3’,4’:5,6]Pyrido[2,3-d]Pyrimidine-Triones under Microwave Irradiation." Journal of Chemical Research 42, no. 12 (2018): 604–7. http://dx.doi.org/10.3184/174751918x15414289771620.

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A green and efficient method for preparing novel heterocyclic systems is established through the reaction of differently substituted benzaldehydes, barbituric acid and 4-amino-2H-chromene-2-one under solvent-free conditions. This method affords 6H-chromeno[3’,4’:5,6] pyrido[2,3-d]pyrimidine-trione derivatives in high yields and short reaction times.

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19

Mohamed, Hany M., and Ashraf H. F. Abd El-Wahab. "Heteroaromatization with 4-Phenyldiazenyl-1-naphthol. Part IV: Synthesis of Some New Heterocyclic Compounds with Potential Biological Activity." Current Organic Synthesis 16, no. 6 (2019): 931–38. http://dx.doi.org/10.2174/1570179416666190719101727.

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Background: Synthetic azo compounds and their derivatives have been studied extensively due to their biological and pharmacological activities. Pyranopyridines, pyranopyrimidines and tetrazoles derivatives have emerged as a promising and attractive scaffold in the development of potent biological and pharmacological agents. Objectives: To design a series of new benzochromeno(pyridine/pyrimidine/tetrazole) derivatives and evaluate their antimicrobial activity against some bacterial strains (Gram-positive and Gram-negative) and some fungal strains. Materials and Methods: The (E)-7-(4-chloropheny

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20

Hesse, Stéphanie, Enrico Perspicace, and Gilbert Kirsch. "Microwave-assisted synthesis of 2-aminothiophene-3-carboxylic acid derivatives, 3H-thieno[2,3-d]pyrimidin-4-one and 4-chlorothieno[2,3-d]pyrimidine." Tetrahedron Letters 48, no. 30 (2007): 5261–64. http://dx.doi.org/10.1016/j.tetlet.2007.05.136.

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Dashyan, Sh Sh, E. G. Paronikyan, A. S. Ayvazyan, S. S. Mamyan, and L. S. Hunanyan. "Synthesis and Prediction of Antitumor Activity of New Fused Pyrano[3,4-c]pyridines and Pyrano[4′,3′:4,5]pyrido[2,3-d]pyrimidines." Russian Journal of General Chemistry 92, no. 3 (2022): 383–92. http://dx.doi.org/10.1134/s1070363222030069.

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Abstract One-pot methods were developed for the preparation of 6-amino-3-isopropyl-7-aryl substituted-8-thioxo(oxo)pyrano[3,4-c]pyridines derivatives. The latter served as starting materials for the synthesis of a new pyrano[4′,3′:4,5]pyrido[2,3-d]pyrimidine heterosystems. The proposed mechanisms of one-pot reactions were presented. Antitumor activity of new synthesized compounds was predicted by in silico methods.

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Bazgir, Ayoob, Maryam Mohammadi Khanaposhtani, and Ali Abolhasani Soorki. "One-pot synthesis and antibacterial activities of pyrazolo[4′,3′:5,6]pyrido[2,3-d]pyrimidine-dione derivatives." Bioorganic & Medicinal Chemistry Letters 18, no. 21 (2008): 5800–5803. http://dx.doi.org/10.1016/j.bmcl.2008.09.057.

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23

Kanevskaya, I. V., N. V. Pchelintseva та O. V. Fedotova. "Functionalization of 4-hydroxy-6-methyl-2Н-pyran-2-one under the conditions of the modified Biginelli reaction". Журнал органической химии 59, № 4 (2023): 466–74. http://dx.doi.org/10.31857/s0514749223040055.

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The features of the interaction of 4-hydroxy-6-methyl-2 H -pyran-2-one with aromatic aldehydes and urea in the one-pot mode of the classical mode, as well as using thermal and microwave activation of The Biginelli reaction variants, were studied. Depending on the conditions of single-reactory processes, previously unknown 3-[amino(aryl)methyl]-4-hydroxy-6-methyl-2 H -pyran-2-one, arylmethylenebis-4-hydroxy-6-methyl-2 H -pyran2-one, hybrid system - 2-hydroxy-7-methyl-4-(3-nitrophenyl)-4,4a-dihydro-5 H -pyrano[4,3- d ]pyrimidine-5-one in the case of transformation with aryl aldehyde containing a

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Marchalín, Štefan, Františka Pavlíková, and Dušan Ilavský. "Synthesis and spectral properties of pyrrolo[3',4':5,6]-4H-pyrano[2,3-d]pyrimidine derivatives." Collection of Czechoslovak Chemical Communications 54, no. 5 (1989): 1336–45. http://dx.doi.org/10.1135/cccc19891336.

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The starting 2-amino-5-ethoxycarbonyl-6-chloromethyl-4-(2-furyl)-3-cyano-4H-pyran (I) afforded on condensation with triethoxymethane 2-ethoxymethylenamino-4H-pyran II; treatment of the latter with ammonia yielded 2-formamidino-3-cyano-4H-pyran III, which, when heated in dilute ethanol, cyclized to 4-amino-6-ethoxycarbonyl-5-(2-furyl)-7-chloromethyl-4H-pyrano[2,3-d]pyrimidine (IV). Compound IV reacted with alkyl- or arylamines to give substituted 5H,6H,8H-pyrrolo[3',4':5,6]-4H-pyrano[2,3-d]pyrimidines VI, one of which (VIb, R = p-CH3C6H4) was alternatively obtained from 2-formamidino-4H-pyrano

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Chiriapkin, A., I. Kodonidi, A. Ivchenko, and L. Smirnova. "Synthesis and Prognosis of Anti-inflammatory Activity of 2-substituted 5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidine-4(3h)-one." Bulletin of Science and Practice 7, no. 12 (2021): 25–33. http://dx.doi.org/10.33619/2414-2948/73/02.

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The article presents a modified method for the synthesis of 2-substituted 5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidine-4(3H)-one and the predict of their anti-inflammatory activity. The proposed method for obtaining tetrahydrothienopyrimidine derivatives is preparatively effective and simple. Their synthesis was carried out by heterocyclization of azomethine derivatives of 2-amino-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxamide in the medium of glacial acetic acid with the catalytic addition of dimethyl sulfoxide. Preliminary prognosis of anti-inflammatory activity in silico method al

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Velihina, Y. S., S. G. Pilyo, I. V. Ivanova, and V. S. Brovarets. "Synthesis of pyrazolo[1,5-a][1,3,5]triazine and oxazolo[4,5-d]pyrimidine derivatives and study of their vasodilator activity." Voprosy Khimii i Khimicheskoi Tekhnologii, no. 2 (May 2023): 51–60. http://dx.doi.org/10.32434/0321-4095-2023-147-2-51-60.

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A number of pyrazolo[1,5-a][1,3,5]triazine and oxazolo[4,5-d]pyrimidine derivatives were synthesized and characterized. Pyrazolo[1,5-a][1,3,5]triazines with various substituents in the fourth position and a dichloromethyl group in the second position were obtained by the heterocyclization reaction of available N-(2,2-dichloro-1-cyanoethenyl)carboxamides and 5-aminopyrazoles. Oxazolo[4,5-d]pyrimidines were obtained by treating 2-phenyl-4-dichloromethylene-1,3-oxazol-5(4H)-one with the corresponding arylamidine hydrochloride in the presence of triethylamine. The resulting 4,5-dihydro-1H-imidazol

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Abu-Hashem, Ameen Ali, and Sami A. Al-Hussain. "Design, Synthesis of New 1,2,4-Triazole/1,3,4-Thiadiazole with Spiroindoline, Imidazo[4,5-b]quinoxaline and Thieno[2,3-d]pyrimidine from Isatin Derivatives as Anticancer Agents." Molecules 27, no. 3 (2022): 835. http://dx.doi.org/10.3390/molecules27030835.

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The current work aims to design and synthesis a new series of isatin derivatives and greatly enhances their cytotoxic activity. The derivatives 3-((bromophenyl) imino)-1-(morpholino (pyridine) methyl) indolin-2-one, 2-((oxoindoline) amino) benzoic acid, 3-(thiazolo-imino) indolinone, ethyl-2-((oxoindolin-3-ylidene)amino)-benzothiophene-3-carboxylate, 1-(oxoindoline)-benzo[4,5] thieno [2,3-d]pyrimidin-4(1H)-one, ethyl-2-(2-oxoindoline) hydrazine-1-carboxylate, N-(mercapto-oxo-pyrimidine)-2-(oxoindoline) hydrazine-1-carboxamide, N-(oxo-thiazolo[3,2-a] pyrimidine)-2-(oxoindolin-ylidene) hydrazine

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28

Gad, Emad M., Mohamed S. Nafie, Elsayed H. Eltamany, Magdy S. A. G. Hammad, Assem Barakat, and Ahmed T. A. Boraei. "Discovery of New Apoptosis-Inducing Agents for Breast Cancer Based on Ethyl 2-Amino-4,5,6,7-Tetra Hydrobenzo[b]Thiophene-3-Carboxylate: Synthesis, In Vitro, and In Vivo Activity Evaluation." Molecules 25, no. 11 (2020): 2523. http://dx.doi.org/10.3390/molecules25112523.

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A multicomponent synthesis was empolyed for the synthesis of ethyl 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate 1. An interesting cyclization was obtained when the amino-ester 1 reacted with ethyl isothiocyanate to give the benzo[4,5]thieno[2,3-d][1,3]thiazin-4-one 3. Acylation of the amino-ester 1 with chloroacetyl chloride in DCM and Et3N afforded the acylated ester 4. The amino-ester 1 was cyclized to benzo[4,5]thieno[2,3-d]pyrimidin-4(3H)-one 8, which was reacted with some alkylating agents leading to alkylation at nitrogen 9–13. Hydrazide 14 was utilized as a synthon for the

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29

Chavda, Mukesh M., Manoj F. Dhaduk, and Jatin M. Upadhyay. "Synthesis, characterization and biological study of some new substituted pyrazolo[3,4-d] thiazolo[3,2-a] pyrimidine derivatives." Current Chemistry Letters 12, no. 4 (2023): 831–38. http://dx.doi.org/10.5267/j.ccl.2023.3.010.

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Fused pyrimidines play an imperative role in our life due to their biological importance in the struggle of microorganisms. A series of 4-aryl-3-methyl-1-phenyl-1,4,6,7-tetrahydropyrazolo[3,4-d] thiazolo[3,2-a]pyrimidine (4a-j) were synthesized by cyclization of 3-methyl-1-phenyl-4-aryl-1,4,5,7-tetrahydro-6H-pyrazolo[3,4-d]pyrimidine-6-thiones (3a-j) with 1,2-dibromoethane in presence of anhydrous potassium carbonate. Earlier, compounds (3a-j) were synthesized by the condensation of 5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one (2), different substituted benzaldehyde and thiourea with catalyt

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30

Ghahremanzadeh, Ramin, Maryam Sayyafi, Somayeh Ahadi, and Ayoob Bazgir. "Novel One-Pot, Three-Component Synthesis of Spiro[Indoline-pyrazolo[4′,3′:5,6]pyrido[2,3-d]pyrimidine]trione Library." Journal of Combinatorial Chemistry 11, no. 3 (2009): 393–96. http://dx.doi.org/10.1021/cc8001958.

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31

Sun, Cheng Yu, Chen Chen, Chun Jiang Wu, Peng Wu Zheng, and Wu Fu Zhu. "Design, Synthesis and Anticancer Activity of 4-Morpholinothieno[3,2-D]-Pyrimidine Derivatives Bearing Chromone Moiety." Advanced Materials Research 989-994 (July 2014): 568–71. http://dx.doi.org/10.4028/www.scientific.net/amr.989-994.568.

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A series of 4-morpholinothieno [3,2-d] pyrimidine derivatives containing chromone moiety (5a-5e) were synthesized and their structures were confirmed by 1H NMR and MS spectrum. The synthesized compounds were evaluated for their cytotoxicity against three cancer cell lines (PC-3, H460, SGC-7901). Two of them exhibited moderate cytotoxicity and high-selectivity against one or more cell lines. At 10μM levels, the inhibition rate of compound 5c against SGC-7901 cell lines was 58.9%, and that of compound 5d against PC-3 cell lines was 56.4%.

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32

Farat, O. K., E. V. Zaliznaya, S. A. Varenichenko, and V. I. Markov. "Rearrangement of substituted pyrimidin-4-ones under the Vilsmeier-Haack reaction." Voprosy Khimii i Khimicheskoi Tekhnologii, no. 1 (January 2021): 101–9. http://dx.doi.org/10.32434/0321-4095-2021-134-1-101-109.

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The article describes the result of our study on rearrangements of four heterocyclic systems with variation of oxygen and nitrogen atoms, in particular, the results of formylation of 2,2-disubstituted hydroquinazolones under the conditions of the Vilsmeier-Haack reaction. A new rearrangement of spiro derivatives of quinazolin-4(3H)-ones was discovered under the action of a formylating reagent with the formation of predicted 1-cyclohex(pent)-1-en-1-ylchinazolin-4-(1H)-ones. The absence of this rearrangement for 2,2-dimethyl-2,3-dihydroquinazolin-4(1H)-one is explained. 6',7',7'-Trimethyl-1',5',

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33

Rahman Badal, Md Mizanur, Md Tarikul Islam, Reshma Parvin, et al. "Antimicrobial, Structure-Activity Relationship and Computational Studies of Some Synthesized Chalcone Derivatives." Asian Journal of Chemistry 33, no. 3 (2021): 644–50. http://dx.doi.org/10.14233/ajchem.2021.23028.

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Several chalcones viz. 1,3-diaryl-2-propane-1-one (1a), 3-(4-hydroxy phenyl)-1-phenyl-2-propane-1- one (1b), 3-(4-amino-phenyl)-1-phenyl-2-propane-1-one (1c) and their derivatives 2-ethoxy-4,6- diphenyl-4H-pyran-3-carboxylic acid ethyl ester (2a), 4-(4-hydroxy-phenyl)-7,7-dimethyl-2-phenyl- 4,6,7,8-tetrahydro-chromen-5-one (2b) and 7-(4-amino-phenyl)-5-phenyl-1,5-dihydropyrano[2,3- d]pyrimidine-2,4-dione (2c ) have been synthesized following both conventional and microwave irradiation methods. The structures of the isolated compounds were elucidated on the basis of UV-visible, FTIR, 1H NMR spe

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34

El-mahdy, Kamelia, Azza El-Kazak, Mohamed Abdel-Megid, Magdy Seada, and Osama Farouk. "Synthesis, Characterization and Biological Evaluation of some New Thieno[2,3-d]Pyrimidine Derivatives." JOURNAL OF ADVANCES IN CHEMISTRY 5, no. 1 (2009): 581–91. http://dx.doi.org/10.24297/jac.v5i1.937.

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10-Oxo-4,6,7,8,9,10-hexahydroprazolo[1,5-a][1]benzothieno[2,3-d]pyrimidine-3-carbaldehyde (2) was prepared by Vilsmeier-Haack reaction of 3-amino-2-methyl-5,6,7,8-tetrahydro[1]benzothieno[2,3-d]pyrimidin-4(3H)-one (1). Reaction of carbaldehyde derivative 2 with malononitrile afforded arylidene malononitrile 3. Cyclization of the latter compound with thiourea yielded pyrimidinethione 4. Interaction of carbaldehyde derivative 2 in presence of thiourea with keto- compounds such as ethyl acetoacetate, or acetylacetone, or dimedone or ethyl cyanoacetate gave pyrimidine derivatives 5-8. Hydrazinolys

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35

Kaliendina, S., M. Brynzei, M. Kut, S. M. Sukharev, Е. Ostapchuk та M. Onysko. "Kaliendina S., Brynzei M., Kut M., Sukharev S.M., Ostapchuk Е., Onysko M. REGIOSELECTIVITY OF ALKYLATION OF 2-(THIOPHENE-2-IL)THIENO[2,3 d]PYRIMIDINE-4(3H)-ONE". Scientific Bulletin of the Uzhhorod University. Series «Chemistry» 50, № 2 (2024): 40–45. http://dx.doi.org/10.24144/2414-0260.2023.2.40-45.

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Thieno[2,3-d]pyrimidines are an important class of heterocyclic compounds with a wide range of biological activities. The thieno[2,3-d]pyrimidin-4-one system is of the greatest interest to scientists, as it is one of a large number of possible thienopyrimidine derivatives. The presence of an amide fragment in these molecules allows for the introduction of various substituents via alkylation reactions. On the other hand, the presence of N- and O-nucleophilic centres makes it possible to form different types of alkylation products. In the present work, the alkylation reaction of 5,6-dimeth

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36

Rahmati, Abbas, and Zahra Khalesi. "A one-pot, three-component synthesis of spiro[indoline-isoxazolo[4′,3′:5,6]pyrido[2,3-d]pyrimidine]triones in water." Tetrahedron 68, no. 40 (2012): 8472–79. http://dx.doi.org/10.1016/j.tet.2012.07.073.

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37

Moustafa, Moustafa Sherief, Saleh Mohammed Al-Mousawi, Maghraby Ali Selim, Ahmed Mohamed Mosallam, and Mohamed Hilmy Elnagdi. "Organobase-catalyzed three-component reactions for the synthesis of 4H-2-aminopyrans, condensed pyrans and polysubstituted benzenes." Beilstein Journal of Organic Chemistry 10 (January 14, 2014): 141–49. http://dx.doi.org/10.3762/bjoc.10.11.

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Novel routes for the preparation of 2-amino-4H-pyran-3-carbonitrile 9, amino-arylbenzoic acid ester derivatives 13a,b, 2-aminotetrahydro-4H-chromene-3-carbonitrile 18, 3-amino-4-cyanotetrahydronaphthalene-2-carboxylic acid ester 26 and 4-amino-3,5-dicyanophthalic acid ester derivatives 37a–c were developed. The synthetic methods utilize one-pot reactions of acetylene carboxylic acid esters, α,β-unsaturated nitriles and/or active methylenenitriles in the presence of L-proline or DABCO. Plausible mechanisms are suggested for the formation of the products. Finally, these compounds were used for t

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38

Abdel-Rahman, Abdu E., Etify A. Bakhite, and Elham A. Al-Taifi. "Fluorine-containing Heterocycles: Part II Synthesis and Reactions of New Thieno[2,3-b]Pyridine Derivatives Bearing Trifluoromethyl Group." Journal of Chemical Research 2005, no. 7 (2005): 461–68. http://dx.doi.org/10.3184/030823405774309014.

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Ethyl [3-cyano-6-(2-thienyl)-4-trifluoromethylpyridin-2-ylthio]acetate (2) and ethyl 3-amino-6-(2-thienyl)-4-trifluoromethylthieno[2,3-b]pyridine-2-carboxylate (3) were prepared by reaction of 3-cyano-6-(2-thienyl)-4-trifluoromethylpyridine-2(1H)-thione (1) with ethyl chloroacetate. The reaction of both 2 and 3 with hydrazine hydrate under different conditions was studied. The main products were [3-cyano-6-(2-thienyl)-4-trifluoromethyl-2-pyridinylthio]acetohydrazide (4) and 3-amino-6-(2-thienyl)-4-trifluoromethylthieno[2,3-b]pyridine-2-carbohydrazide (5). The condensation of acethydrazide 4 wi

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39

Saleh, Mohamed B., Saad S. M. Hassan, Ahmed A. Abdel Gaber, and Nahed A. Abdel Kream. "A novel uranyl ion-selective PVC membrane sensor based on 5,6,7,8-tetrahydro-8-thioxopyrido[4′,3′,4,5]thieno[2,3-d]pyrimidine-4(3H)one." Sensors and Actuators B: Chemical 94, no. 2 (2003): 140–44. http://dx.doi.org/10.1016/s0925-4005(03)00274-0.

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40

Laurenzana, Ilaria, Antonella Caivano, Francesco La Rocca, et al. "A Pyrazolo[3,4-d]Pyrimidine Compound Reduces Fyn Phosphorylation and Induces Apoptosis in Large Granular Lymphocyte Leukemia Cells." Blood 126, no. 23 (2015): 3254. http://dx.doi.org/10.1182/blood.v126.23.3254.3254.

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Abstract Introduction According to WHO classification, large granular lymphocyte leukemia (LGL leukemia) includes three entities: T-cell LGL leukemia, chronic NK lymphoproliferative disorders (NK-CLPD) and aggressive NK cell leukemia. Since no standard therapies for immature NK cell neoplasms have been established so far and the overall outcomes are dismal, new therapeutic options are needed. A pyrazolo[3,4-d]pyrimidine library of compounds have already been studied in a previous work by Tintori et al. It has been demonstrated that one of these compounds proved to be efficient against some mem

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41

Altowyan, Mezna Saleh, Matti Haukka, Saied M. Soliman, Assem Barakat, Ahmed T. A. Boraei, and Manar Sopaih. "Synthesis of a Novel Hydrazone of Thieno[2,3-d]pyrimidine Clubbed with Ninhydrin: X-ray Crystal Structure and Computational Investigations." Crystals 13, no. 3 (2023): 384. http://dx.doi.org/10.3390/cryst13030384.

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The novel hydrazone-containing thieno[2,3-d]pyrimidine, namely, N′-(1,3-dioxo-1,3-dihydro-2H-inden-2-ylidene)-2-(4-oxo-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-3(4H)-yl)acetohydrazide 4 was synthesized in a very good yield from the reaction of the triketoester 1 or ninhydrin 2 with the exocyclic acetohydrazide 3 in methanol. Good-quality crystals of 4 were obtained by recrystallization of the compound from the DMF/MeOH solvent mixture. The target product 4 crystallized in the triclinic crystal system and P-1 space group. The topology analysis of molecular packing indicated that the H

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42

Kshatriya, Monika R., and Jinal A. Gajjar. "Development of novel spiro benzotriazole-based compounds with 1,3-dicarbonyl scaffolds via one-pot synthesis." Current Chemistry Letters 14, no. 3 (2025): 681–86. https://doi.org/10.5267/j.ccl.2025.1.004.

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In the present study, it was demonstrated that a new series of derivatives of 1,2-diphenyl-3H-spiro[benzo[d]pyrrolo[2,1-b]triazol-3,5′-pyrimidine (4) and 3,2′-indandione (6) were efficiently designed and synthesized via a novel, and less cumbersome one-pot methodology involving tri-component interactions among benzotriazole, 2-chloro-2-phenylacetophenone, and 1,3-dicarbonyl compounds in CH₂Cl₂ at room temperature 25°C for 3 hours without the use of a catalyst. The resulting compounds' structural configurations were verified with NMR, IR, EI-MS, and elemental analysis exhibiting good yield and

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43

Marchalín, Štefan, Dušan Ilavský, Jaroslav Kováč, and Milan Bruncko. "Synthesis and reactions of 5-acetyl-2-amino-3-cyano-4-(5-X-2-furyl)-6-methyl-4H-pyrans." Collection of Czechoslovak Chemical Communications 55, no. 3 (1990): 718–27. http://dx.doi.org/10.1135/cccc19900718.

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Substituted 2-amino-4-(5-X-2-furyl)-4H-pyrans IIIa-IIIe have been prepared by a cyclization reaction of 5-X-2-furylmethylenepropanedinitriles IIa-IIe with 2,4-pentanedione. In reaction of 3-(5-X-2-furyl)-methylene-2,4-pentanediones Ia-Ie with propanedinitrile the formation of 4H-pyrans IIIa-IIIe is accompanied, depending on the catalyst type, by the formation of 5-X-2-furylmethylenepropanedinitriles IIa-IIe. 2-(4-Methylbenzylideneamino)-4H-pyran (V), 2-formylamino-4H-pyran (VI), and 3H, 5H-pyrano[2,3-d]pyrimidine-4-one (VII) have been synthesized by functional modifications of the amino group

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44

Rahmati, Abbas, and Zahra Khalesi. "ChemInform Abstract: A One-Pot, Three-Component Synthesis of Spiro[indoline-isoxazolo[4′,3′:5,6]pyrido[2,3-d]pyrimidine]triones in Water." ChemInform 44, no. 9 (2013): no. http://dx.doi.org/10.1002/chin.201309160.

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45

S. Mehdhar, Fatima, Abdullah Y. A. Alzahrani, Ebrahim Abdel-Galil, Ghada E. Abdel-Ghani, Ali Saeed, and Ehab Abdel-Latif. "Synthesis of some new thiophene-based compounds and evaluations of their cytotoxic activities." Bulletin of the Chemical Society of Ethiopia 37, no. 2 (2022): 373–89. http://dx.doi.org/10.4314/bcse.v37i2.10.

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ABSTRACT. A series of new thiophene derivatives was prepared through nucleophilic substitution reactions of the precursor N-(4-substituted-phenyl)-5-(2-chloroacetamido)-4-cyano-3-methylthiophene-2-‎carboxamides 4a and 4b with different sulfur and/or nitrogen nucleophilic reagents (namely; mercaptoacetic acid, 2-mercaptobenzothiazole, 5-(phenylamino)-1,3,4-thiadiazole-2-thiol, 2-mercapto-4,6-dimethylnicotinonitrile, 3-arylazo-4-mercapto-4-(phenylamino)-but-3-en-one derivatives, ammonium thiocyanate, piperidine and/or morpholine). The structures of the prepared thiophene compounds were character

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46

Fattahi, Mehri, Abolghasem Davoodnia, Mehdi Pordel, S. Ali Beyramabadi, and Niloofar Tavakoli-Hoseini. "Isolation of intermediates in the synthesis of new 3,4-dihydro-2H-chromeno[2,3-d]pyrimidines." Zeitschrift für Naturforschung B 73, no. 8 (2018): 557–63. http://dx.doi.org/10.1515/znb-2018-0042.

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AbstractReaction of N-alkyl-2-imino-2H-chromene-3-carboxamides with dimethyl acetylenedicarboxylate (DMAD) in the presence of sodium carbonate as catalyst in refluxing ethanol gave new tricyclic products identified as methyl 3-alkyl-2-(2-methoxy-2-oxoethyl)-4-oxo-3,4-dihydro-2H-chromeno[2,3-d]pyrimidine-2-carboxylates. In the absence of sodium carbonate, dimethyl 2-((E)-3-(alkylcarbamoyl)-2H-chromen-2-ylideneamino)fumarates were isolated as intermediates. These intermediates could be successfully converted to the same new tricyclic products by heating in ethanol containing sodium carbonate. Al

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47

Rigi, Fatemeh, and Hamid Reza Shaterian. "Silica Ammonium Acetate(SiO2-NH4OAc) Catalyzed Facial Synthesis of Dihydropyrazolo[4',3':5,6]Pyrano[2,3-d]Pyrimidine-5,7-Diones." Acta Chemica Iasi 26, no. 1 (2018): 45–58. http://dx.doi.org/10.2478/achi-2018-0004.

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Abstract Silica ammonium acetate (SiO2-NH4OAc) was applied as an inexpensive, practical and heterogeneous catalyst for the preparation of new and known dihydropyrazolo[4',3':5,6]pyrano[2,3-d]pyrimidine-5,7-diones via one-pot four-component reaction of hydrazine hydrate, ethyl acetoacetate aldehydes and barbituric acid/dimethyl barbituric acid under solvent-free conditions. Silica supported ammonium acetate (SiO2-NH4OAc) was prepared according to easy procedure under ambient condition. After completion of the reaction, the catalyst was separated by filtration and reused. So, recycling system, s

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48

Ye, Zhong-Li, Guang-Hua Xin, Fu-Tian Zhang та Dong-Rong Xiao. "Diaqua(5-carboxybenzene-1,3-dicarboxylato-κO1)[8-ethyl-5-oxo-2-(piperazin-4-ium-1-yl)-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylato-κ2O5,O6]zinc monohydrate". Acta Crystallographica Section E Structure Reports Online 69, № 2 (2013): m127. http://dx.doi.org/10.1107/s1600536813002122.

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In the title compound, [Zn(C14H17N5O3)(C9H4O6)(H2O)2]·H2O, the complex molecule exists in a zwitterionic form. The ZnIIion exhibits a distorted tetragonal-pyramidal geometry, being coordinated by two O atoms from the zwitterionic 8-ethyl-5-oxo-2-(piperazin-4-ium-1-yl)-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylate (L) ligand, one O atom from the 5-carboxybenzene-1,3-dicarboxylate dianion, [Hbtc]2−, and two O atoms from two aqua ligands. In the crystal, N—H...O and O—H...O hydrogen bonds link the components into a three-dimensional structure. The crystal packing exhibits π–π interactions betw

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49

Janeba, Zlatko, Jan Balzarini, Graciela Andrei, Robert Snoeck, Erik De Clercq, and Morris J. Robins. "Synthesis and biological evaluation of 5-(alkyn-1-yl)-1-(p-toluenesulfonyl)uracil derivatives." Canadian Journal of Chemistry 84, no. 4 (2006): 580–86. http://dx.doi.org/10.1139/v06-041.

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Sonogashira coupling of 5-iodouracil (2) and trimethylsilylacetylene gave 5-(trimethylsilylethynyl)uracil (3), which was deprotected to give 5-ethynyluracil (4). Copper(I)-catalyzed cyclization of 4 gave furo[2,3-d]pyrimidin-2(3H)-one (5). Tosylation of 2 and 4 gave the 1-(p-toluenesulfonyl) derivatives 6 and 7, respectively. The tosylated compound 6 and trimethylsilylacetylene did not undergo Sonogashira coupling, and copper(I)-catalyzed cyclization of 7 did not occur. Coupling of 2 with several terminal alkynes gave 5-(alkyn-1-yl)uracil derivatives (9), which underwent tosylation to produce

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50

Patel, A. J., and M. P. Patel. "ULTRASOUND PROMOTED L- PROLINE CATALYZED FACILE SYNTHESIS AND ANTIMICROBIAL EVALUATION OF 4H-CHROMENO[2,3-D] PYRIMIDINE DERIVATIVES INCORPORATED WITH QUINOLINE MOIETY." INDIAN DRUGS 54, no. 09 (2017): 16–23. http://dx.doi.org/10.53879/id.54.09.11091.

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A simple, straightforward synthesis of 5-(2-chloro-6-substitutedquinolin-3-yl)-2-(4-substitutedphenyl)-8,8- substituted-5,7,8,9-tetrahydro-4H-chromeno[2,3-d]pyrimidine-4,6(3H)-diones (4a-l) has been performed by ultrasound irradiation method. Targeted compounds (4a-l) prepared from reaction of intermediate 2-amino-4-(2-chloro-6-substituted quinolin-3-yl)-7,7-substituted-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3- carbonitrile 2, which is synthesized by one pot three components way using L-proline as green catalyst at room temperature, was further reacted with benzaldehyde derivatives in the same r

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