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Journal articles on the topic 'Pyrimidines. Pyrimidines'

Author: Grafiati

Published: 4 June 2021

Last updated: 1 February 2022

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1

Nwachukwu, Chideraa I., Leanna J. Patton, Nathan P. Bowling, and Eric Bosch. "Ditopic halogen bonding with bipyrimidines and activated pyrimidines." Acta Crystallographica Section C Structural Chemistry 76, no. 5 (2020): 458–67. http://dx.doi.org/10.1107/s2053229620005082.

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The potential of pyrimidines to serve as ditopic halogen-bond acceptors is explored. The halogen-bonded cocrystals formed from solutions of either 5,5′-bipyrimidine (C8H6N4) or 1,2-bis(pyrimidin-5-yl)ethyne (C10H6N4) and 2 molar equivalents of 1,3-diiodotetrafluorobenzene (C6F4I2) have a 1:1 composition. Each pyrimidine moiety acts as a single halogen-bond acceptor and the bipyrimidines act as ditopic halogen-bond acceptors. In contrast, the activated pyrimidines 2- and 5-{[4-(dimethylamino)phenyl]ethynyl}pyrimidine (C14H13N3) are ditopic halogen-bond acceptors, and 1:1 halogen-bonded cocrysta

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2

Verma, Vishal, Chandra Prakash Joshi, Alka Agarwal, Sakshi Soni, and Udichi Kataria. "A Review on Pharmacological Aspects of Pyrimidine Derivatives." Journal of Drug Delivery and Therapeutics 10, no. 5 (2020): 358–61. http://dx.doi.org/10.22270/jddt.v10i5.4295.

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Pyrimidine is an aromatic heterocyclic organic compound similar to pyridine. One of the three diazines (six-membered heterocyclics with two nitrogen atoms in the ring), it has the nitrogens at positions 1 and 3 in the ring. Pyrimidines are typically synthesized by the “Principal Synthesis” involving cyclization of beta-dicarbonyl compounds with N-C-N compounds. Reaction of the former with amidines to give 2-substituted pyrimidines, with urea to give 2-pyrimidiones, and guanidines to give 2-aminopyrimidines are typical. Pyrimidines can be prepared via the biginelli reaction. Many other methods

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3

Borrell, José I., Jordi Teixidó, Blanca Martínez-Teipel, et al. "An Unequivocal Synthesis of 4-Amino-1,5,6,8-tetrahydropyrido[2,3-d]pyrimidine-2,7-diones and 2-Amino-3,5,6,8-tetrahydropyrido[2,3-d]pyrimidine-4,7-diones." Collection of Czechoslovak Chemical Communications 61, no. 6 (1996): 901–9. http://dx.doi.org/10.1135/cccc19960901.

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An unequivocal set of procedures for the synthesis of 4-amino-1,5,6,8-tetrahydropyrido[2,3-d]pyrimidine-2,7-diones (7) and 2-amino-3,5,6,8-tetrahydropyrido[2,3-d]pyrimidine-4,7-diones (8), in a maximum of four steps from an α,β-unsaturated ester 1, is reported. Thus, the acid hydrolysis of the 2,4-diaminopyrido[2,3-d]pyrimidines 3 yields the 4-amino-2-oxopyrido[2,3-d]pyrimidines 7 while the cyclization of the Michael adducts 9 (formed by reaction of 1 and methyl cyanoacetate) with guanidine affords the corresponding 2-amino-4-oxopyrido[2,3-d]pyrimidines 8. Both isomers were also obtained by hy

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4

Mohammed, F. K., and M. G. Badrey. "Synthesis of Pyrimidines and Heteroannulated Pyrimidine Ring Systems." Journal of the Korean Chemical Society 55, no. 2 (2011): 218–29. http://dx.doi.org/10.5012/jkcs.2011.55.2.218.

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5

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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6

Behera, Manoranjan, M. Sambaiah, Poosa Mallesham, et al. "Tandem Schiff-Base Formation/Heterocyclization: An Approach to the Synthesis of Fused Pyrazolo–Pyrimidine/Isoxazolo-Pyrimidine Hybrids." Synlett 30, no. 05 (2019): 586–92. http://dx.doi.org/10.1055/s-0037-1612081.

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A new synthesis of pyrazolo[4,3-d]pyrimidines and isoxazolo[4,5-d]pyrimidines is described. Key steps in the synthesis involve Stille coupling of 4,6-dichloro-2-phenyl-pyrimidine with tributyl(1-ethoxyvinyl)stannane and tandem Schiff-base formation/heterocyclization of 2,6-di-aryl-5-fluoro-4-acetylpyrimidine with hydrazines or hydroxylamine to give pyrazolo[4,3-d]pyrimidines and isoxazolo[4,5-d]pyrimidines, respectively. The position of the fluoro group in the pyrimidine ring is important for the success of heterocylization reaction.

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7

Sirakanyan, Spinelli, Geronikaki, et al. "Synthesis, Antitumor Activity, and Docking Analysis of New Pyrido[3’,2’:4,5]furo(thieno)[3,2-d]pyrimidin-8-amines." Molecules 24, no. 21 (2019): 3952. http://dx.doi.org/10.3390/molecules24213952.

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Continuing our research in the field of new heterocyclic compounds, herein we report on the synthesis and antitumor activity of new amino derivatives of pyrido[3’,2’:4,5](furo)thieno[3,2-d]pyrimidines as well as of two new heterocyclic systems: furo[2–e]imidazo[1,2-c]pyrimidine and furo[2,3-e]pyrimido[1,2-c]pyrimidine. Thus, by refluxing the 8-chloro derivatives of pyrido[3’,2’:4,5]thieno(furo)[3,2-d]pyrimidines with various amines, the relevant pyrido[3’,2’:4,5]thieno(furo)[3,2-d]pyrimidin-8-amines were obtained. Further, the cyclization of some amines under the action of phosphorus oxychlori

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8

Solomyannyi, Roman, Sergii Slivchuk, Donald Smee, et al. "In vitro Activity of the Novel Pyrimidines and Their Condensed Derivatives Against Poliovirus." Current Bioactive Compounds 15, no. 5 (2019): 582–91. http://dx.doi.org/10.2174/1573407214666180720120509.

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Background: Substituted pyrimidine derivatives (non-nucleoside) are found to be associated with various biological activities. The various substituted pyrimidines are also having significant in vitro activity against different DNA and RNA viruses. The present study focuses on the anti-PV activity of new pyrimidines and their condensed derivatives. Methods: A series of novel pyrimidines and their condensed derivatives were synthesized and their structures were confirmed by spectral data. Their antiviral activities against poliovirus type 3 (PV-3) were evaluated in vitro. In cell culture, morpho

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9

Gallagher, P. E., and N. J. Duker. "Detection of UV purine photoproducts in a defined sequence of human DNA." Molecular and Cellular Biology 6, no. 2 (1986): 707–9. http://dx.doi.org/10.1128/mcb.6.2.707.

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The UV-irradiated, 3'-end-labeled, 92-base-pair terminus of the human alphoid sequence was incubated with purified endonuclease v. Previously unreported photoproducts were incised at purine loci. These were not pyrimidine photodimers, 6-4'-(pyrimidin-2'-one)-pyrimidines, base loss sites, or ring-opened purines. Therefore, purine-containing photoproducts, possibly dimers, were incised by the enzyme preparation.

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10

Gallagher, P. E., and N. J. Duker. "Detection of UV purine photoproducts in a defined sequence of human DNA." Molecular and Cellular Biology 6, no. 2 (1986): 707–9. http://dx.doi.org/10.1128/mcb.6.2.707-709.1986.

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The UV-irradiated, 3'-end-labeled, 92-base-pair terminus of the human alphoid sequence was incubated with purified endonuclease v. Previously unreported photoproducts were incised at purine loci. These were not pyrimidine photodimers, 6-4'-(pyrimidin-2'-one)-pyrimidines, base loss sites, or ring-opened purines. Therefore, purine-containing photoproducts, possibly dimers, were incised by the enzyme preparation.

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11

Nerkar, A. G., S. A. Ghone, and A. K. Thaker. "In SilicoScreening of the Library of Pyrimidine Derivatives as Thymidylate Synthase Inhibitors for Anticancer Activity." E-Journal of Chemistry 6, no. 3 (2009): 665–72. http://dx.doi.org/10.1155/2009/352717.

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We here report the virtual screening of several series of pyrimidine derivatives forin silicoThymidylate Synthase (TS) inhibition to arrive at possible potential inhibitors of TS with acceptable pharmacokinetic or ADME (Absorption, Distribution, Metabolism and Excretion) properties. Library of the molecules was constructed based upon structural modifications of pyrimidines nucleus. Structural modifications in descending order were performed for the series of pyrimidines,vizfrom pyrimidines with five membered heterocyclic ring to pyrimidines with four membered heterocyclic ring to simple pyrimi

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12

Popa, Marcel Mirel, Emilian Georgescu, Mino R. Caira, et al. "Indolizines and pyrrolo[1,2-c]pyrimidines decorated with a pyrimidine and a pyridine unit respectively." Beilstein Journal of Organic Chemistry 11 (June 26, 2015): 1079–88. http://dx.doi.org/10.3762/bjoc.11.121.

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The three possible structural isomers of 4-(pyridyl)pyrimidine were employed for the synthesis of new pyrrolo[1,2-c]pyrimidines and new indolizines, by 1,3-dipolar cycloaddition reaction of their corresponding N-ylides generated in situ from their corresponding cycloimmonium bromides. In the case of 4-(3-pyridyl)pyrimidine and 4-(4-pyridyl)pyrimidine the quaternization reactions occur as expected at the pyridine nitrogen atom leading to pyridinium bromides and consequently to new indolizines via the corresponding pyridinium N-ylides. However, in the case of 4-(2-pyridyl)pyrimidine the steric h

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13

Liu, Xianxian, and Rebecca E. Parales. "Chemotaxis of Escherichia coli to Pyrimidines: a New Role for the Signal Transducer Tap." Journal of Bacteriology 190, no. 3 (2007): 972–79. http://dx.doi.org/10.1128/jb.01590-07.

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ABSTRACT Escherichia coli exhibits chemotactic responses to sugars, amino acids, and dipeptides, and the responses are mediated by methyl-accepting chemotaxis proteins (MCPs). Using capillary assays, we demonstrated that Escherichia coli RP437 is attracted to the pyrimidines thymine and uracil and the response was constitutively expressed under all tested growth conditions. All MCP mutants lacking the MCP Tap protein showed no response to pyrimidines, suggesting that Tap, which is known to mediate dipeptide chemotaxis, is required for pyrimidine chemotaxis. In order to confirm the role of Tap

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14

Bischoff, Kerstin, Ulrich Girreser, Dieter Heber, and Martin Schütt. "Two-Step Synthetic Approach to 6-Substituted Pyrido[2,3-d]pyrimidine(1H,3H)-2,4-diones from 6-Amino-, 6-Alkylamino-, and 6-Arylamino-1,3-dimethyluracils." Zeitschrift für Naturforschung B 61, no. 4 (2006): 486–94. http://dx.doi.org/10.1515/znb-2006-0415.

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The Mannich reaction of 7-aryl-5,6-dihydropyrido[2,3-d]pyrimidines 3, easily accessible by condensation of 6-amino-1,3-dimethyluracil (1) with Mannich bases 2a - c, gives rise to a mixture of 7-aryl-6-(N,N-dimethylaminomethyl)pyrido[2,3-d]pyrimidines 6 and 7 as well as 1,2-bis- (7-arylpyrido[2,3-d]pyrimidin-6-yl)ethane 13 the ratio of which depends on the reaction conditions and the amine used. 6-Alkylamino-1,3-dimethyluracils 15 - 18 were converted to the corresponding 5-(3-oxo-3-phenylpropyl)uracils 19 - 22 by condensation with the Mannich base 2a. Ring closure of 19 - 22 was performed by Vi

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15

Verbitskiy, Egor, Gennady Rusinov, Oleg Chupakhin, and Valery Charushin. "Recent Advances in Direct C–H Functionalization of Pyrimidines." Synthesis 50, no. 02 (2017): 193–210. http://dx.doi.org/10.1055/s-0036-1589520.

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Data spanning the period 2000–2017 on the direct C–H functionalization of pyrimidines are collected and discussed in this review. This demonstrates the surge of interest and creativity that this field of chemistry has experienced during the last two decades. Plausible applications of highly functionalized pyrimidines are also discussed.1 Introduction2 Transition-Metal-Catalyzed C–H Functionalization of Pyrimidine Derivatives3 Transition-Metal-Free Direct C–H Functionalization of Pyrimidine Derivatives4 Deprotonative Metalation of Pyrimidine Derivatives5 Conclusions

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16

Dawood, Dina H., Eman M. H. Abbas, Thoraya A. Farghaly, Mamdouh M. Ali, and Mohammed F. Ibrahim. "ZnO Nanoparticles Catalyst in the Synthesis of Bioactive Fused Pyrimidines as Anti-breast Cancer Agents Targeting VEGFR-2." Medicinal Chemistry 15, no. 3 (2019): 277–86. http://dx.doi.org/10.2174/1573406414666180912113226.

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Background: Pyrimidines emerged as a remarkable class of heterocyclic compounds that have reinforced the pharmaceutical chemistry with various bioactive antitumor agents. Moreover, pyrimidine scaffold displayed VEGFR-2 inhibitory activity. Also, nano-sized catalysts are used in organic reactions in order to speed up the catalytic process. Objective: We were interested herein to synthesize a new series of fused pyrimidines using ZnO(NPs) to investigate their antitumor efficiency against breast MCF7 cancer and their VEGFR- 2 inhibition properties. Method: A simple and efficient method for the sy

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17

Ogurtsov, Vladimir, and Oleg Rakitin. "4-Chloro-6-(chloromethyl)-1-methyl-1H-pyrazolo[3,4-d]pyrimidine." Molbank 2021, no. 3 (2021): M1253. http://dx.doi.org/10.3390/m1253.

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A novel 4-chloro-6-(chloromethyl)-1-methyl-1H-pyrazolo[3,4-d]pyrimidine was prepared by a rational and short two-step synthesis from commercially available ethyl 5-amino-1-methyl-1H-pyrazole-4-carboxylate via 6-(chloromethyl)-1-methyl-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one. The structure of the synthesized compounds was established by elemental analysis, high-resolution mass-spectrometry, 1H, 13C-NMR and IR spectroscopy and mass-spectrometry. 4-Chloro-6-(chloromethyl)-1-methyl-1H-pyrazolo[3,4-d]pyrimidine is a convenient intermediate for various disubstituted 1-methyl-1H-pyrazolo[3,4-d]

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18

Hocková, Dana, Milena Masojídková, and Antonín Holý. "Sonogashira Cross-Coupling in the Synthesis of Acyclic Nucleoside Phosphonates: Preparation of 6-[(Phosphonomethoxy)alkynyl]- and 6-[(Phosphonomethoxy)alkyl]pyrimidines." Collection of Czechoslovak Chemical Communications 70, no. 2 (2005): 247–58. http://dx.doi.org/10.1135/cccc20050247.

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Several 6-[(phosphonomethoxy)alkyl]pyrimidines and 6-[(phosphonomethoxy)alkynyl]pyrimidines were prepared as saturated and unsaturated carba-analogues of antivirally active 2,4-diamino-6-[2-(phosphonomethoxy)ethoxy]pyrimidine. As the key step of their synthesis the Sonogashira cross-coupling reaction was successfully applied. The replacement of the C-O moiety by the C-C bond resulted in the loss of biological activity.

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19

Mohamed, Mosaad, Ramdan El-Domany, and Rania Abd El-Hameed. "Synthesis of certain pyrrole derivatives as antimicro-bial agents." Acta Pharmaceutica 59, no. 2 (2009): 145–58. http://dx.doi.org/10.2478/v10007-009-0016-9.

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Synthesis of certain pyrrole derivatives as antimicro-bial agentsIn an effort to establish new pyrroles and pyrrolo[2,3-d] pyrimidines with improved antimicrobial activity we report here the synthesis andin vitromicrobiological evaluation of a series of pyrrole derivatives. A series of new 2-aminopyrrole-3-carbonitriles (1a-d) were synthesized from the reaction of benzoin, primary aromatic amines and malononitrile, from which a number of pyrrole derivatives (2a-dto5a-d) and pyrrolo[2,3-d]pyrimidines (6a-dto10a, d) were synthesized. Thein vitroantimicrobial testing of the synthesized compounds

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20

Chandrani, Jeenkal P., and Kalpesh J. Ganatra. "An Efficient And Catalytically Free Chemical Transformation of Pyrimidin-2(1H)-one to 2-(N-Arylamino)pyrimidines and their in vitro Cytotoxicity Evaluation." Asian Journal of Organic & Medicinal Chemistry 5, no. 2 (2020): 133–37. http://dx.doi.org/10.14233/ajomc.2020.ajomc-p260.

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With the aim to develop an efficient strategy to synthesize pyrimidine derivatives bearing diversely substituted amines involves four step linear protocols started with Biginelli multi-component reaction leading to dihydropyrimidines which passing throug multistep sequantial process containing oxidation, chlorination and catalytically free transformation of pyrimidin-2(1H)-one to 2-(N-arylamino)pyrimidines, were evaluated for cytotoxicity study against human cancer lines HCT-116, Hep-G2 and QG-56. Compound 4j exhibit significant anticancer activity showed against: human hepato carcinoma (Hep-G

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21

Cawrse, Brian M., Nia’mani M. Robinson, Nina C. Lee, Gerald M. Wilson, and Katherine L. Seley-Radtke. "Structural and Biological Investigations for a Series of N-5 Substituted Pyrrolo[3,2-d]pyrimidines as Potential Anti-Cancer Therapeutics." Molecules 24, no. 14 (2019): 2656. http://dx.doi.org/10.3390/molecules24142656.

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Pyrrolo[3,2-d]pyrimidines have been studied for many years as potential lead compounds for the development of antiproliferative agents. Much of the focus has been on modifications to the pyrimidine ring, with enzymatic recognition often modulated by C2 and C4 substituents. In contrast, this work focuses on the N5 of the pyrrole ring by means of a series of novel N5-substituted pyrrolo[3,2-d]pyrimidines. The compounds were screened against the NCI-60 Human Tumor Cell Line panel, and the results were analyzed using the COMPARE algorithm to elucidate potential mechanisms of action. COMPARE analys

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22

Greco, Chiara, Rosa Catania, Dario Leonardo Balacco, et al. "Synthesis and Antibacterial Evaluation of New Pyrazolo[3,4-d]pyrimidines Kinase Inhibitors." Molecules 25, no. 22 (2020): 5354. http://dx.doi.org/10.3390/molecules25225354.

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Pyrazolo[3,4-d]pyrimidines represent an important class of heterocyclic compounds well-known for their anticancer activity exerted by the inhibition of eukaryotic protein kinases. Recently, pyrazolo[3,4-d]pyrimidines have become increasingly attractive for their potential antimicrobial properties. Here, we explored the activity of a library of in-house pyrazolo[3,4-d]pyrimidines, targeting human protein kinases, against Staphylococcus aureus and Escherichia coli and their interaction with ampicillin and kanamycin, representing important classes of clinically used antibiotics. Our results repre

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23

Innocenti, Paolo, Hannah Woodward, Lisa O'Fee, and Swen Hoelder. "Expanding the scope of fused pyrimidines as kinase inhibitor scaffolds: synthesis and modification of pyrido[3,4-d]pyrimidines." Organic & Biomolecular Chemistry 13, no. 3 (2015): 893–904. http://dx.doi.org/10.1039/c4ob02238f.

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A versatile and efficient entry into 2-amino-pyrido[3,4-d]pyrimidines was developed. Our strategy hinges on the concise preparation and derivatisation of 8-chloro-2-(methylthio)pyrido[3,4-d]pyrimidine intermediates to yield putative kinase inhibitors.

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24

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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25

Schmidt, Andreas, and Thorsten Mordhorst. "Syntheses and Properties of Di- and Tricationic Hetarenium-Substituted Pyrimidines." Zeitschrift für Naturforschung B 61, no. 4 (2006): 396–405. http://dx.doi.org/10.1515/znb-2006-0405.

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2,4-Dichloro-, 4,6-dichloro-, 2,4,6-trichloro- and tetrachloropyrimidine undergo nucleophilic displacements by 4-(dimethylamino)pyridine to give (pyrimidine-2,4-diyl)-1,1’-bis[4-(dimethylamino) pyridinium] dichloride, (pyrimidine-4,6-diyl)-1,1’-bis[4-(dimethylamino)-pyridinium] dichloride, (pyrimidine-2,4,6-triyl)-1,1’,1”-tris[4-(dimethylamino)pyridinium] trichloride, and (5- chloropyrimidine-2,4,6-triyl)-1,1’,1”-tris[4-(dimethylamino)pyridinium] trichloride, respectively. Nucleophilic substitutions of the pyridinium substituents by O- and S-nucleophiles to functionalized pyrimidines are exami

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26

Lee, Su-Jeong, Jun-Gi Ahn, Jihwan Seo, Heun-Jong Ha, and Chang-Woo Cho. "Organocatalytic enantioselective synthesis of acyclic pyrimidine nucleosides by aza-Michael reaction." Organic & Biomolecular Chemistry 16, no. 48 (2018): 9477–86. http://dx.doi.org/10.1039/c8ob02754d.

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27

Soto-Acosta, Ruben, Eunkyung Jung, Li Qiu, Daniel J. Wilson, Robert J. Geraghty, and Liqiang Chen. "4,7-Disubstituted 7H-Pyrrolo[2,3-d]pyrimidines and Their Analogs as Antiviral Agents against Zika Virus." Molecules 26, no. 13 (2021): 3779. http://dx.doi.org/10.3390/molecules26133779.

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Discovery of compound 1 as a Zika virus (ZIKV) inhibitor has prompted us to investigate its 7H-pyrrolo[2,3-d]pyrimidine scaffold, revealing structural features that elicit antiviral activity. Furthermore, we have demonstrated that 9H-purine or 1H-pyrazolo[3,4-d]pyrimidine can serve as an alternative core structure. Overall, we have identified 4,7-disubstituted 7H-pyrrolo[2,3-d]pyrimidines and their analogs including compounds 1, 8 and 11 as promising antiviral agents against flaviviruses ZIKV and dengue virus (DENV). While the molecular target of these compounds is yet to be elucidated, 4,7-di

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28

Geies, Ahmed A. "Bromonitriles in Heterocyclic Synthesis. Synthesis and Reactions of Thiazolo[3,2-a]pyrimidines (III)." Collection of Czechoslovak Chemical Communications 57, no. 7 (1992): 1565–69. http://dx.doi.org/10.1135/cccc19921565.

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As a continuation of our previous work about the synthesis and properties of thiazolopyrimidines, which are expected to be of biological and medicinal importance, the present work is aimed to synthesize new polyfunctional substituted thiazolo[3,2-a]pyrimidines. Pyrimidine derivatives I were reacted with bromomalononitrile or ethyl bromocyanoacetate at room temperature in ethanol in presence of potassium hydroxide as a basic catalyst followed by refluxing the reaction mixture to give thiazolo[3,2-a]pyrimidines IIa-IId.

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29

K, Ishwar Bhat, and Abhishek Kumar. "PYRIMIDINES AS POTENT CYTOTOXIC AND ANTI-INFLAMMATORY AGENTS." Asian Journal of Pharmaceutical and Clinical Research 10, no. 6 (2017): 237. http://dx.doi.org/10.22159/ajpcr.2017.v10i6.17343.

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Objective: Many derivatives of pyrimidine are known for the broad-spectrum biological activities such as antimicrobial, antitumor, antibacterial, antitubercular, anti-inflammatory, and cytotoxic activity. Chalcones with an enone group show potent pharmacological activities such as antiinflammatory, antibacterial, antifungal, and antimalarial activity. A series of pyrimidines from chalcones have been synthesized and screened for anti-inflammatory and cytotoxic activity studies.Methods: Chalcones [1-(4-nitrophenyl)-3-substituted-phenylprop-2-en-1-one] were synthesized from various substituted al

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30

Sahu, Pramod K., Praveen K. Sahu, Manvendra S. Kaurav, et al. "One-pot facile and mild construction of densely functionalized pyrimidines in water via consecutive C–C and C–S bonds formation." RSC Advances 8, no. 59 (2018): 33952–59. http://dx.doi.org/10.1039/c8ra04363a.

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Fused pyrimidines composed of alternating heteroatoms and a pyrimidine moiety were synthesized efficiently using readily available starting material 4-hydroxycoumarin, aromatic aldehydes, and urea/thiourea at room temperature.

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31

Pandhurnekar, Chandrashekhar P., Ekta M. Meshram, Himani N. Chopde, and Rameshkumar J. Batra. "Synthesis, Characterization, and Biological Activity of 4-(2-Hydroxy-5-(aryl-diazenyl)phenyl)-6-(aryl)pyrimidin-2-ols Derivatives." Organic Chemistry International 2013 (July 1, 2013): 1–10. http://dx.doi.org/10.1155/2013/582079.

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With the aim of synthesizing new heterocyclic compounds and exploring biological potency, new series of chalcones, that is, 3-(2-hydroxy-5-(aryl-diazenyl)phenyl)-1-(aryl)prop-2-en-1-one and their pyrimidine derivatives, that is, 4-(2-hydroxy-5-(aryl-diazenyl)phenyl)-6-(aryl)pyrimidin-2-ols were synthesized using different aromatic amines and salicylaldehyde as starting moieties. The structures of newly synthesized compounds were confirmed using different spectroscopic techniques such as IR, 1H-NMR, 13C-NMR, and mass spectral analysis, and elemental analysis. The newly synthesized pyrimidines d

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32

Vanderhaeghe, H., and M. Claesen. "Pyrimidines II-Dérivés des acides pyrimidine-carboxyliques." Bulletin des Sociétés Chimiques Belges 66, no. 1 (2010): 276–91. http://dx.doi.org/10.1002/bscb.19570660123.

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33

Romero-Ortega, Moisés, Michelle Trujillo-Lagunas, Ignacio Medina-Mercado, Ivann Zaragoza-Galicia, and Horacio Olivo. "A Synthesis of 4-Chloro-2-(trichloromethyl)pyrimidines and Their Study in Nucleophilic Substitution." Synthesis 51, no. 02 (2018): 530–37. http://dx.doi.org/10.1055/s-0037-1610270.

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A convenient two-step, one-pot synthesis of 4-chloro-2-(trichloromethyl)pyrimidines starting from 2-(trichloromethyl)-1,3-diazabutadienes is described. These nitrogen heterocycles were prepared by a sequential acylation/intramolecular cyclization reaction between 2-(trichloromethyl)-1,3-diazabutadienes and acyl chlorides in the presence of triethylamine followed by treatment with POCl3. This is the first report for the synthesis of this type of 4-chloro-2-(trichloromethyl)pyrimidine derivatives and serves as a source for a wide variety of other substituted pyrimidines by nucleophilic substitut

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34

Shehab, Wesam S., Mohamed G. Assy, Hamed Y. Moustafa, Magda H. Abdellattif, and Hamdi M. A. Rahman. "Pyrimidines as block units in heterocycles: novel synthesis of pyrimidines and condensed pyrimidine derivatives." Journal of the Iranian Chemical Society 16, no. 11 (2019): 2451–61. http://dx.doi.org/10.1007/s13738-019-01712-4.

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35

Dodonova, Jelena, and Sigitas Tumkevicius. "Fused Pyrrolo[2,3-d]pyrimidines (7-Deazapurines) by Palladium-Catalyzed Direct N–H and C–H Arylation Reactions." Synthesis 49, no. 11 (2017): 2523–34. http://dx.doi.org/10.1055/s-0036-1588734.

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Palladium-catalyzed intramolecular direct C–H arylations for the synthesis of hitherto unknown fused hetero systems containing an incorporated pyrrolo[2,3-d]pyrimidine scaffold are described. Pyrimido[5′,4′:4,5]pyrrolo[2,1-a]isoindoles were synthesized from 2,4-diarylpyrrolo[2,3-d]pyrimidines and o-bromobenzyl bromides by using a cascade N-benzylation/C–H arylation reaction sequence. A series of pyrimido[5′,4′:4,5]pyrrolo[1,2-f]phenanthridines were successfully assembled via a domino process involving the palladium-catalyzed direct double C–H arylation reactions of 2,4,7-triarylpyrrolo[2,3-d]

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36

Zhou, Jing, Zhengtong Mao, Haokun Pan, and Xingxian Zhang. "Pd-Catalyzed highly selective and direct ortho C–H arylation of pyrrolo[2,3-d]pyrimidine derivatives." Organic Chemistry Frontiers 7, no. 2 (2020): 324–28. http://dx.doi.org/10.1039/c9qo01312a.

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Pd-Catalyzed one-pot direct ortho C–H arylation of pyrrolo[2,3-d]pyrimidine derivatives is reported. This protocol provides a variety of biphenyl-containing pyrrolo[2,3-d]pyrimidines in good to excellent yields.

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37

Azam, Mohammed Afzal, Loganathan Dharanya, Charu Chandrakant Mehta, and Sumit Sachdeva. "Synthesis and biological evaluation of some novel pyrazolopyrimidines incorporating a benzothiazole ring system." Acta Pharmaceutica 63, no. 1 (2013): 19–30. http://dx.doi.org/10.2478/acph-2013-0001.

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In the present study, a series of benzothiazol derivatives 3a-l containing pyrazolo[3,4-d]pyrimidine moiety at the second position were synthesized and characterized by analytical and spectral data. The compounds were tested for their in vitro antimicrobial activity. Compounds 1-(1,3-benzothiazol-2- yl)-3-methyl-4-phenyl-1H-pyrazolo[3,4-d]pyrimidine (3a), 1- (1,3-benzothiazol-2-yl)-4-(4-chlorophenyl)-3-methyl-1H-pyrazolo[ 3,4-d]pyrimidine (3d) and 1-(1,3-benzothiazol-2-yl)- 3-methyl-4-substituted phenyl-1H-pyrazolo[3,4-d]pyrimidines (3h-j) showed significant inhibitory activity against P. aeru

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38

Mao, Zhengtong, Min Liu, Gaoyang Zhu, Jing Zhou, and Xingxian Zhang. "Transition-metal-free highly regioselective C–H acetoxylation of pyrrolo[2,3-d]pyrimidine derivatives." Organic Chemistry Frontiers 7, no. 18 (2020): 2696–702. http://dx.doi.org/10.1039/d0qo00702a.

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Transition-metal-free catalyzed direct C(sp<sup>2</sup>)–H acetoxylation of pyrrolo[2,3-d]pyrimidine derivatives is reported. This protocol provides a variety of acetoxylated pyrrolo[2,3-d]pyrimidines in good to excellent yields.

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39

Prager, RH, and Y. Singh. "The Chemistry of 5-Oxodihydroisoxazoles. IX. Annelated Pyrimidines by Flash Vacuum Pyrolysis." Australian Journal of Chemistry 47, no. 7 (1994): 1263. http://dx.doi.org/10.1071/ch9941263.

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3-( Heterocyclylamino ) acrylates and analogues undergo smooth cyclization in close to quantitative yield under conditions of flash vacuum pyrolysis at 530°. Heterocycles which give annelated pyrimidines by this procedure include quinoline (seven examples), isoquinoline, pyridine and pyrimidine.

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40

Vincetti, Paolo, Gabriele Costantino, Maria Grazia Martina, and Marco Radi. "Probing the Reactivity of 2,4-Dichlorofuro[3,4-d]pyrimidin-7-one: A Versatile and Underexploited Scaffold to Generate Substituted or Fused Pyrimidine Derivatives." Synlett 30, no. 17 (2019): 2010–14. http://dx.doi.org/10.1055/s-0039-1690205.

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Herein, we describe the results of our investigation on the chemical reactivity and versatility of a poorly explored scaffold: 2,4-dichlorofuro[3,4-d]pyrimidin-7-one (3). Highly functionalized pyrimidines can be obtained with a divergent approach by reacting the key intermediate 3 with different amine nucleophiles under carefully controlled reaction conditions. The set-up of a microwave-assisted one-pot, two- or three-step protocol to rapidly generate 2,4,5,6-tetrasubstituted or fused pyrimidines is also reported.

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41

Kokorekin, Vladimir A., Sergey V. Neverov, Vera N. Kuzina, and Vladimir A. Petrosyan. "A New Method for the Synthesis of 3-Thiocyanatopyrazolo[1,5-a]pyrimidines." Molecules 25, no. 18 (2020): 4169. http://dx.doi.org/10.3390/molecules25184169.

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In this article, we demonstrate how an original effective “metal-free” and “chromatography-free” route for the synthesis of 3-thiocyanatopyrazolo[1,5-a]pyrimidines has been developed. It is based on electrooxidative (anodic) C–H thiocyanation of 5-aminopyrazoles by thiocyanate ion leading to 4-thiocyanato-5-aminopyrazoles (stage 1, yields up to 87%) following by their chemical condensation with 1,3-dicarbonyl compounds or their derivatives (stage 2, yields up to 96%). This method is equally effective for the synthesis of 3-thiocyanatopyrazolo[1,5-a]pyrimidines, both without substituents and wi

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42

Kalita, Subarna Jyoti, Dibakar Chandra Deka, and Hormi Mecadon. "Organocatalytic domino Knöevenagel–Michael reaction in water for the regioselective synthesis of benzo[4,5]imidazo[1,2-a]pyrimidines and pyrido[2,3-d]pyrimidin-2-amines." RSC Advances 6, no. 94 (2016): 91320–24. http://dx.doi.org/10.1039/c6ra21376f.

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43

Ahmed, Essam Kh, Mohamed A. Ameen, and Fathy F. Abdel-Latif. "Microwave-Assisted Synthesis of Novel Imidazo- and Pyrimidopyrido[4’,3’:4,5]thieno[2,3-d]pyrimidines." Zeitschrift für Naturforschung B 60, no. 2 (2005): 221–26. http://dx.doi.org/10.1515/znb-2005-0216.

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It is reported on the microwave-assisted synthesis of imidazo- and pyrimidopyrido [4’,3’:4,5]thieno[ 2,3-d]pyrimidines from 2-ethoxymethylene-amino-3-cyano-4,5,6,7-tetrahydrothieno[2,3-c]- pyridine-6-carboxylic acid ethyl ester and 4-chloro-pyridothieno[2,3-d]pyrimidine.

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44

Ho, Yuh-Wen, and Maw Cherng Suen. "Thioxopyrimidine in Heterocyclic Synthesis I: Synthesis of Some Novel 6-(Heteroatom-substituted)-(thio)pyrimidine Derivatives." Journal of Chemistry 2013 (2013): 1–15. http://dx.doi.org/10.1155/2013/765243.

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A series of novel N-cycloalkanes, morpholine, piperazines, pyrazole, pyrimidine, benzimidazolo[1,2-a]pyrimidine, 1,2,3,4-tetrazolo[1,5-a]pyrimidine, azopyrazolo[1,5- a]pyrimidine, pyrimido[4', 5':3,4]pyrazolo[1,5-a]pyrimidines and pyridine derivatives incorporating a 5-cyano-4-methyl-2-phenyl-(thio)pyrimidine moiety were obtained by the intramolecular cyclization of 6-methylthio-pyrimidine, 6-(benzoylmethyl)thio- pyrimidine and 2-[(5-cyano-4-methyl-2-phenylpyrimidin-6-yl)thio]-3-dimethyl- amino-1-phenyl-prop-2-en-1-one with appropriate amines and enaminone compounds, respectively. The structur

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45

Stentoft, Charlotte, Betina Amdisen Røjen, Søren Krogh Jensen, Niels B. Kristensen, Mogens Vestergaard, and Mogens Larsen. "Absorption and intermediary metabolism of purines and pyrimidines in lactating dairy cows." British Journal of Nutrition 113, no. 4 (2015): 560–73. http://dx.doi.org/10.1017/s0007114514004000.

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About 20 % of ruminal microbial N in dairy cows derives from purines and pyrimidines; however, their intermediary metabolism and contribution to the overall N metabolism has sparsely been described. In the present study, the postprandial patterns of net portal-drained viscera (PDV) and hepatic metabolism were assessed to evaluate purine and pyrimidine N in dairy cows. Blood was sampled simultaneously from four veins with eight hourly samples from four multi-catheterised Holstein cows. Quantification of twenty purines and pyrimidines was performed with HPLC–MS/MS, and net fluxes were estimated

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46

Dolšak, Ana, Kristjan Mrgole, and Matej Sova. "Microwave-Assisted Regioselective Suzuki Coupling of 2,4-Dichloropyrimidines with Aryl and Heteroaryl Boronic Acids." Catalysts 11, no. 4 (2021): 439. http://dx.doi.org/10.3390/catal11040439.

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Suzuki coupling reaction has been often used for the preparation of a diverse set of substituted pyrimidines. In this study, the Suzuki coupling of 2,4-dichloropyrimidines with aryl and heteroaryl boronic acids was investigated. A thorough screening of reaction conditions and the use of microwave irradiation led to a very efficient and straightforward synthetic procedure providing C4-substituted pyrimidines in good to excellent yields. Short reaction time (15 min) and extremely low catalyst loading (0.5 mol%) are the main advantages of our tetrakis(triphenylphosphine)palladium(0) catalyzed mic

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47

Gein, V. L., A. N. Prudnikova, A. A. Kurbatova, and M. V. Dmitriev. "Synthesis of (E)-5-Arylvinyl-7-methyltetrazolo[1,5-a]pyrimidines." Russian Journal of General Chemistry 91, no. 4 (2021): 621–25. http://dx.doi.org/10.1134/s1070363221040071.

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Abstract A three-component reaction of 5-aminotetrazole with aromatic aldehydes and acetylacetone under solvent- and catalyst-free conditions at a temperature of 150–160°С proceeds with the formation of (E)-5-arylvinyl-7-methyltetrazolo[1,5-a]pyrimidines. 5,7-Dimethyltetrazolo[1,5-a]pyrimidine is formed as a side-product of the reaction.

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48

Szennyes, Eszter, Gyöngyi Gyémánt, László Somsák та Éva Bokor. "Synthesis of New Series of 2-C-(β-D-glucopyranosyl)-Pyrimidines and Their Evaluation as Inhibitors of Some Glycoenzymes". Molecules 25, № 3 (2020): 701. http://dx.doi.org/10.3390/molecules25030701.

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Despite the substantial interest in C-glycosyl heterocycles as mimetics of biologically active native glycans, the appearance of C-glycopyranosyl derivatives of six-membered heterocycles, both in synthetic and biological contexts, is rather scarce. As part of our ongoing research program aimed at preparing hitherto barely known 2-C-glycopyranosyl pyrimidines, the goal of the present study was to synthesize new 5-mono- and multiply substituted derivatives of this compound class. Thus, 2-C-(β-D-glucopyranosyl)-5,6-disubstituted-pyrimidin-4(3H)-ones and 4-amino-2-C-(β-D-glucopyranosyl)-5,6-disubs

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49

Yang, Wen-Juan, Qiu Sun, Jing Sun, and Chao-Guo Yan. "Domino aza/oxa-hetero-Diels–Alder reaction for construction of novel spiro[pyrido[3′,2′:5,6]pyrano[2,3-d]pyrimidine-7,5′-pyrimidine]." Organic Chemistry Frontiers 5, no. 18 (2018): 2754–58. http://dx.doi.org/10.1039/c8qo00784e.

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The unprecedented reaction of α,β-unsaturated N-arylaldimines with two molecular 5-arylidene-1,3-dimethylbarbituric acids in methylene dichloride at room temperature afforded unique spiro[pyrido[3′,2′:5,6]pyrano[2,3-d]pyrimidine-7,5′-pyrimidines] in moderate to good yields and with high diastereoselectivity.

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50

Mamaghani, Manouchehr. "Ultrasound-promoted synthesis of novel dihydropyrido[2,3-d:5,6- d`]dipyrimidine derivatives." JOURNAL OF ADVANCES IN CHEMISTRY 11, no. 5 (2015): 3567–75. http://dx.doi.org/10.24297/jac.v11i5.4475.

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An efficient synthesis of dihydropyrido[2,3-d:5,6-d`]pyrimidine derivatives was developed via one-pot three-component reaction of 6-amino-2-(alkylthio)-pyrimidine-4(3H)one and aryl aldehydes in the mixed solvent of glacial acetic acid and DMF (1:1, v:v) under ultrasonic irradiation. In this protocol novel fused dihydropyrido[2,3-d]pyrimidines were synthesized in high yields (80-97%) and lower reaction times (5-25 min).

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