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Journal articles on the topic '5-trione'

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Published: 4 June 2021

Last updated: 13 February 2022

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1

Hanson, James R., Ismail Kiran, Natheer F. Masarweh, and Cavit Uyanik. "Preparation of Androst-5-ene-4,7,17-trione and A-Norandrost-5-ene-3,7,17-trione." Journal of Chemical Research, no. 9 (1998): 493. http://dx.doi.org/10.1039/a803764g.

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2

Hanson, James R., Ismail Kiran, Natheer F. Masarweh, and Cavit Uyanik. "ChemInform Abstract: Preparation of Androst-5-ene-4,7,17-trione and A-Norandrost-5-ene-3,7,17-trione." ChemInform 30, no. 15 (June 16, 2010): no. http://dx.doi.org/10.1002/chin.199915226.

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3

Bartke, Michael, and Wolfgang Pfleiderer. "Pteridines, XC Syntheses, Oxidations, Properties, and Reactions of 2-Thiopteridine-4,6, 7- trione Derivatives." Pteridines 1, no. 2 (May 1989): 83–90. http://dx.doi.org/10.1515/pteridines.1989.1.2.83.

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Summary A new efficient synthesis for 2-thiopteridine-4,6,7-triones (6-10, 15) has been found in the condendation of the appropriate 5,6-diaminopyrimidine (1-5, 14) with oxalic acid in DMF. Analogous condensations with dimethyl oxalate led to S-alkylation probably via an intermediate O-methylation of the DMF. 8-Methyl-2- thiopteridine-4,6,7-trione (10) shows a ring contraction to 9-methyl-2-thioxanthine (13) on base treatment. Oxidations by H20 2 and KMn04 respectively lead to the corresponding 2-sulfinate 22 and the 2-sulfonates 17 -19. Oxidative desulfurization takes place in formic acid with H 20 2 forming first the sulfinate 22, which then eliminates S02 to give pteridine-4,6,7-trione (23). Nucleophilic displacements of the 2-sulfonate group by ammonia and amines form the corresponding leucopterin derivatives 20, 21 and 24. The newly synthesized compounds have been characterized by elemental analyses, UV-spectra and pKa-determinations. The ionization sequences of the acidic hydrogens have been assigned based on these physical data .

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4

Kobyzhcha, N. I., V. S. Pyliavskyi, V. V. Sukhoveev, and V. I. Kashkovskyi. "Derivatives of pyrimidine-2,4,6-triones as components of additives to increase the lubricating properties of motor fuels." Catalysis and petrochemistry, no. 30 (2020): 97–101. http://dx.doi.org/10.15407/kataliz2020.30.097.

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One of the important tasks of modern petrochemistry is the development of new additives that can improve the performance of motor fuels. With the expansion of the number of automotive and agricultural machinery and increasing its technical level, the demand for a wider range of petroleum products is increasing and, as well, the requirements for their quality are increasing. As the environmental and operational requirements for motor fuels are constantly increasing, it is necessary to find new, more efficient additives. The paper describes the synthesis of spirocyclic pyrimidine-2,4,6-trionеs by ring-closing metathesis reactions (RCM). This type of transformation is actively used in petrochemical and organic syntheses and allows to obtain compounds that are difficult to synthesize by conventional methods of organic chemistry. RCM conversion was performed using a Grubbs-Hoveyda catalyst in an amount of 5 mol. %. The compounds formed during the reaction were investigated as additives to motor fuels. Studies of the effect of synthesized spiropyrimidine-2,4,6-trione derivatives as additives on the tribological characteristics of ethanol and diesel fuel were evaluated on a four-ball tribometer in terms of critical load. At least three experiments were performed at each load. The error of the experiment was less than 5%. It was found that substances 2c and 2b increase the lubricating properties of ethanol - the critical load to the fuel burr when adding the synthesized compounds increased by 25%. Spiropyrimidine-2,4,6-trione 2b also had a positive effect on the lubricity of diesel fuel and had the effect of increasing the load to burr by 12% at a concentration of 0.032%. Thus, derivatives of spiropyrimidine-2,4,6-triones have proven to be promising compounds for the manufacture of motor fuels.

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5

Fazldeen, H. "Oxidation of Isomuellitol and Hexahydromuellitol With Chromium Trioxide." Australian Journal of Chemistry 40, no. 5 (1987): 999. http://dx.doi.org/10.1071/ch9870999.

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Chromate oxidation of isomuellitol (2) led cleanly to the production of a cyclic trione , 2,2,9,9,15,15-hexamethyl- 1,8,14-trioxatrispiro [4.1.4.1.4.l]octadecane-6,12,18-trione (4), but the product derived from hexahydromuellitol (3) was an unexpected γ-lactone, 4-hydroxy-2,4-bis(3′-methylbutyl )-3-(4″-methyl-1″-oxopentyloxy)-5-oxotetrahydrofuran-2-carboxylic acid (5).

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6

Al-Sheikh, Ahmad, Kamal Sweidan, Norbert Kuhn, Cäcilia Maichle-Mößmer, and Manfred Steimann. "Elimination of a Thiomethyl Substituent from an Anionic 5-Methylenebarbituric Acid Derivative by Oxidation and Substitution." Zeitschrift für Naturforschung B 64, no. 3 (March 1, 2009): 307–12. http://dx.doi.org/10.1515/znb-2009-0309.

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Triethylammonium 5-[(1,3-dimethyl-2,4,6-trioxo-tetrahydropyrimidin-5(6H)-ylidene)-(methylthio) methyl]-1,3-dimethyl-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-olate (5), obtained from 5-[bis (methylthio)methylene]-1,3-dimethyl-2,4,6(1H,3H,5H)-pyrimidinetrione (2) and 1,3-dimethylbarbituric acid in the presence of triethylamine, is protonated by methanesulfonic acid to give 5,5ʹ-(methylthiomethanediylidene)bis(1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione) (6) in good yield. Compound 6 is oxidized in two steps by m-chloroperbenzoic acid to give 5,5ʹ- (methylsulfinylmethanediylidene)bis(1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione) (7) and 5-[(1,3-dimethyl-2,4,6-trioxo-tetrahydropyrimidin-5(6H)-ylidene)(methylsulfinyl)methyl]-5-hydroxy- 1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione (8), respectively. Excess pyridine eliminates methanesulfinic acid from 8 to give the zwitterionic 5-[(1,3-dimethyl-2,4,6-trioxo-tetrahydropyrimidin- 5(6H)-ylidene(pyridinium-1-yl)methyl]-1,3-dimethyl-2,6-dioxo-1,2,3,6-tetrahydropyrimidin- 4-olate (9). The crystal structures of compounds 6, 8, and 9 are reported.

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7

Collins, DJ, and NE Krause. "Monoacetals Derived From 12-α-Hydroxyandrosta-1,4-diene-3,17-dione and Androsta-1,4-diene-3,12,17-trione." Australian Journal of Chemistry 41, no. 6 (1988): 985. http://dx.doi.org/10.1071/ch9880985.

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Conversion of 12α-hydroxyandrosta-1,4-diene-3,17-dione (5) into the corresponding 17-cyclic ethylene acetal (1) was accompanied by acid- catalysed attack of ethylene glycol at C3 to give 17,17-ethylenedioxy- 3-(2′-hydroxyethoxy)-1-methylestra-1,3,5(10)-trien-12a-ol (2), which was the major product with prolonged reaction times. Exchange dioxolanation of androsta-1,4-diene-3,12,17-trione (8), prepared by Jones oxidation of (5), gave selectively the 12-monoacetal (9): the regioisomeric 17-monoacetal (4) was obtained by oxidation of the hydroxy acetal (1) with chromium trioxide in pyridine. The trione (8) likewise afforded selectively the 12,12-ethylenedithio acetal (11). Treatment of the trione (8) with p- toluenesulfonic acid in refluxing benzene gave 1-hydroxy-4-methylestra-1,3,5(10)-triene-12,17- dione (7a).

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8

Gohain, Mukut, Theunis J. Muller, and Barend C. B. Bezuidenhoudt. "5-(3,4-Dimethoxybenzylidene)-1,3-dimethyl-1,3-diazinane-2,4,6-trione." Acta Crystallographica Section E Structure Reports Online 68, no. 1 (December 21, 2011): o179. http://dx.doi.org/10.1107/s1600536811052986.

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9

Lewis, William, Robert H. McKeown, and Ward T. Robinson. "(\pm)-5-Ethyl-1-methyl-5-phenylpyrimidine-2,4,6-trione at 163 K." Acta Crystallographica Section E Structure Reports Online 61, no. 4 (March 4, 2005): o799—o800. http://dx.doi.org/10.1107/s1600536805005593.

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10

Hökelek, Tuncer, Zeynel Seferoğlu, Ertan Şahin, and Nermin Ertan. "5-[(5-Methylthiazol-2-yl)diazenyl]pyrimidine-2,4,6(1H,3H,5H)-trione." Acta Crystallographica Section E Structure Reports Online 63, no. 3 (February 28, 2007): o1506—o1508. http://dx.doi.org/10.1107/s1600536807009051.

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In the molecular structure of the title compound, C8H7N5O3S, the thiazole ring is oriented with respect to the barbituric acid ring at a dihedral angle of 5.14 (9)°. In the crystal structure, intermolecular N—H...N and N—H...O hydrogen bonds link the molecules, forming a layer parallel to the ac plane.

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11

Sweidan, Kamal, Norbert Kuhn, Cäcilia Maichle-Mößmer, and Manfred Steimann. "Reaction of a Zwitterionic Pyridinium Ylide with N,N-Dimethylaniline." Zeitschrift für Naturforschung B 65, no. 1 (January 1, 2010): 99–100. http://dx.doi.org/10.1515/znb-2010-0118.

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1,3-Dimethyl-2,4,6-trioxo-5-pyridinomethyl-1,3-perhydrodiazin- 5-ylpyridinium ylide (3) reacts with N,N-dimethylaniline to give 5-((1,3-dimethyl-2,4,6-trioxo-hexahydropyrimidin- 5-yl)methyl)-5-(4-(dimethylamino)benzyl)-1,3- dimethylpyrimidine- 2,4,6(1H3H5H)-trione (6) in good yield. The crystal structure of 6 is reported

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12

Gelbrich, Thomas, and Ulrich J. Griesser. "Crystal structure of 5-hydroxy-5-propylbarbituric acid." Acta Crystallographica Section E Crystallographic Communications 71, no. 11 (October 14, 2015): 1311–14. http://dx.doi.org/10.1107/s2056989015018769.

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Molecules of the title compound, C7H10N2O4, systematic name 5-hydroxy-5-propylpyrimidine-2,4,6(1H,3H,5H)-trione, form a hydrogen-bonded framework which is based on three independent hydrogen bonds, N—H...O(carbonyl), N—H...O(hydroxy) and O—H...O(carbonyl). This framework has the topology of the 5-connectednovnet. Each molecule is linked to five other moleculesviasix hydrogen bonds, and the descriptor of the hydrogen-bonded structure isF65[44.66-nov]. The crystal packing is isostructural with that of the previously reported 5-hydroxy-5-ethyl analogue.

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13

Piniella, J. F., and J. Rius. "Structure of (5S)-9(10⇒5)abeo-1-estrene-3,10,17-trione." Acta Crystallographica Section C Crystal Structure Communications 44, no. 4 (April 15, 1988): 699–701. http://dx.doi.org/10.1107/s0108270187012356.

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14

Panchatcharam, R., V. Dhayalan, A. K. Mohanakrishnan, G. Chakkaravarthi, and V. Manivannan. "1,3-Dimethyl-5-(2-methylbenzylidene)pyrimidine-2,4,6(1H,3H,5H)-trione." Acta Crystallographica Section E Structure Reports Online 65, no. 10 (September 9, 2009): o2394. http://dx.doi.org/10.1107/s1600536809035521.

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15

Poschenrieder, Hermann, Georg Höfner, and Hans-Dietrich Stachel. "5-Arylidene-pyrrolidine-2,3,4-trione 3-Oximes as NMDA Receptor Antagonists." Archiv der Pharmazie 332, no. 9 (September 1999): 309–16. http://dx.doi.org/10.1002/(sici)1521-4184(19999)332:9<309::aid-ardp309>3.0.co;2-n.

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16

Borg, Bertil, Efthimia Antonopoulou, Eva Andersson, Tomas Carlberg, and Ian Mayer. "Effectiveness of several androgens in stimulating kidney hypertrophy, a secondary sexual character, in castrated male three-spined sticklebacks, Gasterosteus aculeatus." Canadian Journal of Zoology 71, no. 11 (November 1, 1993): 2327–29. http://dx.doi.org/10.1139/z93-326.

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The effectiveness of different androgens in stimulating hypertrophy of the kidney tubules, a male secondary sexual character, was studied by injecting castrated male sticklebacks with androgens at doses of 0.008–25 μg∙g body weight−1∙day−1 (or control injections were given) for 3 weeks. The doses (μg/g) needed to give 50% stimulation of the kidney epithelium height were as follows: 11-ketotestosterone (OT), 0.047; 11β-hydroxyandrostenedione, 0.070; 11-ketoandrostenedione, 0.11; 5α-androstane-3,11,17-trione, 1.1; 5α-dihydrotestosterone, 1.8; 17β-hydroxy-5α-androstane-3,11-dione, 3.0; and testosterone, 15.2. Androstenedione and 5β-androstane-3,11,17-trione did not reach half-effectiveness at the dose tested (5 μg/g). It is suggested that OT is the physiologically relevant androgen in this case.

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17

Liu, Dong-Ze, Qi Liu, Ping Yang, and Wen-Xia Jiang. "A New Ergostane Triterpenoid from Cultures of the Basidiomycete Inocybe lilacina." Natural Product Communications 9, no. 3 (March 2014): 1934578X1400900. http://dx.doi.org/10.1177/1934578x1400900322.

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A new ergostane triterpenoid (4α-methylergost-8,24(28)-dien-3,7,11-trione, 1) together with four known compounds (2–5) were isolated from cultures of the basidiomycete Inocybe lilacina. The structure of the new compound was established on the basis of IR, 1D and 2D NMR spectroscopic and MS experiments.

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18

Subramanyahegde, Hosamani Amar, Yellappa Shivaraj, Giriyapura R. Vijayakumar, and Bandrehalli Siddagangaiah Palakshamurthy. "5′-([1,1′-Biphenyl]-4-yl)-1′,1′′,3′′-trimethyldispiro[indane-2,2′-pyrrolidine-4′,5′′-[1,3]diazinane]-1,3,2′′,4′′,6′′-pentaone." Acta Crystallographica Section E Structure Reports Online 70, no. 7 (June 11, 2014): o759. http://dx.doi.org/10.1107/s1600536814013117.

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In the title compound, C30H25N3O5, the central five-membered heterocyclic ring adopts an envelope conformation, with the N atom as the flap. The dihedral angles between this central ring and the pendant indane ring system, the trione and benzene rings are 87.49 (5), 82.95 (10) and 72.42 (10)°, respectively. The dihedral angle between the rings of the biphenyl group is 45.99 (13)°. In the crystal, molecules are linked by C—H...O hydrogen bonds into [101]C(12) chains.

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19

Obi, Chibuike D., and Cosmas O. Okoro. "Synthesis of 5-(trifluoromethyl)cyclohexane-1,2,3-trione (cVTC): new trifluoromethyl building block." Tetrahedron Letters 57, no. 47 (November 2016): 5259–61. http://dx.doi.org/10.1016/j.tetlet.2016.10.043.

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20

Seferoğlu, Zeynel, Tuncer Hökelek, Ertan Şahin, Mehmet Emin Çelik, and Nermin Ertan. "1,3-Dimethyl-5-(thiazol-2-yldiazenyl)pyrimidine-2,4,6(1H,3H,5H)-trione." Acta Crystallographica Section E Structure Reports Online 62, no. 12 (November 30, 2006): o5855—o5857. http://dx.doi.org/10.1107/s1600536806049816.

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21

Vickery, B., G. R. Willey, and M. G. B. Drew. "Structure of 2,2-dimethyl-1,3-dioxane-4,5,6-trione 5-(2,4-dinitrophenylhydrazone), C12H10N4O8." Acta Crystallographica Section C Crystal Structure Communications 41, no. 4 (April 15, 1985): 586–89. http://dx.doi.org/10.1107/s0108270185004759.

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22

Kumar, Ashish, Yahya E. Jad, Ayman El-Faham, Beatriz G. de la Torre, and Fernando Albericio. "Diethylphosphoryl-OxymaB (DEPO-B) as a Solid Coupling Reagent for Amide Bond Formation." Letters in Organic Chemistry 16, no. 1 (December 4, 2018): 30–33. http://dx.doi.org/10.2174/1570178615666180612074420.

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A new phosphonium based coupling reagent DEPO-B has been synthesized from 5- (hydroxyimino)-1,3-dimethylpyrimidine-2,4,6 (1H,3H,5H)-trione (Oxyma B) and diethyl chlorophosphate in presence of base. It is a solid material and the hydrolytic stability and solubility was evaluated for confirming its capability for usage in automated peptide synthesizer.

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23

Elinson, Michail N., Anatoly N. Vereshchagin, Alexander D. Korshunov, and Mikhail P. Egorov. "A fast and efficient ‘on-solvent’ cascade assembling of salicylaldehydes and dimethylbarbituric acid into 5-(1,3-dimethyl-2,4-dioxo-1,3,4,5-tetrahydro-2H-chromeno[2,3-d]pyrimidin-5-yl)-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-triones." Heterocyclic Communications 24, no. 2 (April 25, 2018): 79–83. http://dx.doi.org/10.1515/hc-2018-0015.

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AbstractA fast (15 min) and efficient cascade reaction of salicylaldehydes and 1,3-dimethylbarbituric acid in the presence ofp-TsOH as a catalyst furnishes substituted 5-(1,3-dimethyl-2,4-dioxo-1,3,4,5-tetrahydro-2H-chromeno[2,3-d]pyrimidin-5-yl)-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-triones1a–h, containing both chromeno[2,3-d]pyrimidine and hexahydropyrimidine-2,4,6-trione pharmacologically active fragments, in 95–99% yields. This new procedure is characterized by the use of inexpensive reagents and a simple workup.

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24

Schmidt, M., K. Albert, R. Brindle, C. Maichle-Mössmer, and K. Eger. "Zur Struktur von Hydroxy-5-phenyl-furanonen: Lösungs-NMR, Festkörper-13C-NMR und Röntgenstruktur im Vergleich / On the Structure of Hydroxy-5-phenyl-furanone Derivatives: NMR Spectroscopy in Solution and High Resolution Solid State 13C NMR Spectroscopy in Relation to X-Ray Crystallography." Zeitschrift für Naturforschung B 48, no. 10 (October 1, 1993): 1372–80. http://dx.doi.org/10.1515/znb-1993-1011.

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The structure of (5H)-2-Amino-3-hydroxy-5-phenyl-furan-4-one (lb) was determined by NMR-spectroscopy in solution and in the solid state. The structure of its oxidation product, 3,4-Dihydro-3,3,4,4-tetrahydroxy-5-phenyl-furan-2(5H)-one (7), given in the literature as 5-Phenyl-2,3,4-(5H)-furan-trione, was determined by NMR spectroscopy and crystal structure analysis. The solid state NMR spectrum of 7 was compared to the spectrum of dehydroascorbic acid

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25

Habashneh, Almeqdad Y., Mustafa M. El-Abadelah, Mohammed M. Abadleh, and Wolfgang Voelter. "Heterocycles [c]-Fused onto Indoloquinoxaline. Synthesis of Novel Pyrano[2’,3’:4,5]indolo[2,3-b]quinoxalin-2-ones." Zeitschrift für Naturforschung B 67, no. 7 (July 1, 2012): 725–30. http://dx.doi.org/10.5560/znb.2012-0131.

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A synthesis of 4-methylpyrano[2,3-e]indole-2,8,9-trione (5) is achieved from 7-amino-4- methylcoumarin by adopting the classical Sandmeyer methodology. The cyclocondensation reaction of pyrano-isatin 5 with the appropriately substituted o-phenylenediamines 6 in polyphosphoric acid proceeded regioselectively to furnish the respective pyrano[2’,3’:4,5]indolo[2,3-b]quinoxalines 7a - c. Structural assignments of the new compounds are based on microanalytical and spectral (IR, MS and NMR) data.

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26

Marcuccio, SM, and JA Elix. "Pyrazine Chemistry. IV. Oxidation of 3,6-Dibenzylpiperazine-2,5-diones." Australian Journal of Chemistry 38, no. 2 (1985): 343. http://dx.doi.org/10.1071/ch9850343.

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The autoxidation of (�) cis- and trans-3,6-dibenzyl-1,4- dimethylpiperazine-2,5-diones (6) and (8) has been shown to give (�)-6- benzyl-1,4-dimethylpiperazine-2,3,5-trione (12). Oxidation of a (2) cis-trans mixture of 1,4-diacetyl-3,6-dibenzylpiperazine-2,5-diones, (5) and (7), with elemental sulfur was shown to give (�)-(Z)-1-acetyl- 6-benzyl-3-benzylidenepiperazine-2,5-dione (10).

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27

Metwally, Mohamed Abbas, and M. A. Sofan. "Synthesis of Some New Pyrrolo Heterocycles of Pharmaceutical Interest from 1,4-Diphenylpyrrolidine-2,3,5-trione+." Zeitschrift für Naturforschung B 45, no. 3 (March 1, 1990): 382–84. http://dx.doi.org/10.1515/znb-1990-0313.

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Continuing earlier studies designed to obtain derivatives of pharmacological interest, some novel compounds 2, 5, 6, 7 and 8 were prepared using 1,4-diphenylpyrrolidine-2,3,5-trione (1) and 1,2-phenylenediamines, o-aminophenol, 1,3-diphenylacetone and thiosemicarbazide, respectively. The hydrazino derivative (8) was obtained from 7 and hydrazine hydrate. Structural identification was obtained by 1H NMR, mass spectra and IR spectral data.

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28

Savchuk, Sergei A., and Igor G. Zenkevich. "Identification of unknown compound extracted from the hair of exhumed human remains using mass spectrometric and gas chromatographic data." Аналитика и контроль 25, no. 1 (2021): 34–42. http://dx.doi.org/10.15826/analitika.2020.25.1.002.

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The real example of GC-MS identification of unknown constituent of human hair extract belonging to the exhumed remains is considered. The identification of this constituent (molecular weight 238 Da) was unsuccessful using both its standard mass spectrum (electron ionization) in combination with library search, and its GC retention index value (~1540 on semi-standard non-polar polydimethyl siloxane stationary phases with 5% phenyl groups). However, its identification appeared to be possible using the original algorithm of data processing. This approach implies revealing the structural analogues of unknown analytes, primarily their homologues which differ by molecular masses on ± 14 Da and by composition on CH2 homologous difference. This approach allowed revealing such analogues of unknown analyte as Flavesone (2,2,4,4-tetramethyl-2-isobutyrylcyclohexa-1,3,5-trione), Leptospermone (2,2,4,4-tetramethyl-2-isopentanoylcyclohexa-1,3,5-trione), and some others. All these compounds belong to a rather “exotic” class of natural compounds knows as cyclic b-triketones. Based on the obtained data, the possible structure of the constituent under the consideration was proposed as 2,2,4,4-tetramethyl-2-propionylcyclohexa-1,3,5-trione. The principal feature of cyclic b-triketones is their existence in a few tautomeric forms. Another tautomer of triketone under discussion is 5-hydroxy-2,2,6,6-tetramethyl-4-propionyl-4-en-1,3-dione (CAS № 87552-01-0). This compound is found to be the constituent of Leptospermum scoparium essential oil and some other plants, and it belongs to the group of structural analogues of Flavesone. The most known pharmaceutical application of essential oils containing these compounds are the components of conditioners for hair and skin. The results confirm this formerly unknown component does not belong to the group of toxic substances. This excludes the criminal origin of the remains.

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29

Mallah, Eyad, Ahmed Al-Sheikh, Kamal Sweidan, Wael Abu Dayyih, and Manfred Steimann. "Crystal structure of 5-[bis(methylsulfonyl)methyl]-1,3-dimethyl-5-(methylsulfonyl)pyrimidine-2,4,6(1H,3H,5H)-trione." Acta Crystallographica Section E Crystallographic Communications 71, no. 1 (January 1, 2015): o58—o59. http://dx.doi.org/10.1107/s2056989014027455.

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In the title compound, C10H16N2O9S3, the pyrimidine ring of the 1,3-dimethyl barbituric acid moiety has an envelope conformation with the C atom carrying the methylsulfonyl and bis(methylsulfonyl)methyl substituents as the flap. The dihedral angle between mean plane of the pyrimidine ring and the S/C/S plane is 72.4 (3)°. In the crystal, molecules are linkedviaC—H...O hydrogen bonds, forming a three-dimensional structure.

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30

Sweidan, Kamal, and Manfred Steimann. "5-[1-(1,3-Dimethyl-2,4,6-trioxohexahydropyrimidin-5-yl)-2-oxopropyl]-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione." Acta Crystallographica Section E Structure Reports Online 69, no. 8 (July 27, 2013): o1334. http://dx.doi.org/10.1107/s1600536813020138.

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31

Ardakani, Leili Shaker, Mohammad Hossein Mosslemin, and Bahareh Sadeghi. "Three-Component Reaction of Alkyl Isocyanide, Acetylenic Diesters and 5-Hydroxy-5- Arylpyrimidine-2,4,6(1H,3H,5H)-Trione." Journal of Chemical Research 39, no. 8 (August 2015): 467–69. http://dx.doi.org/10.3184/174751915x14381554915509.

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32

da Silva, Emerson T., Rodrigo S. Ribiero, Edson L. S. Lima, James L. Wardell, Janet M. S. Skakle, John N. Low, and Christopher Glidewell. "5-(1-Hydroxyethylidene)-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione and four amino derivatives." Acta Crystallographica Section C Crystal Structure Communications 61, no. 1 (December 11, 2004): o15—o20. http://dx.doi.org/10.1107/s0108270104028859.

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33

Ueda, K., M. Iwamatsu, and T. Sugimoto. "1,3,4,6-Tetrathiapentalene-5-spiro-2'-indan-2,1',3'-trione and its 2-thione analogue." Acta Crystallographica Section C Crystal Structure Communications 55, no. 1 (January 15, 1999): IUC9800077. http://dx.doi.org/10.1107/s0108270199099928.

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34

Barakat, Assem, Hazem A. Ghabbour, Bandar M. Al-Qahtani, M. Ali, and Abdullah Mohammed Al-Majid. "Crystal structure of 5-(3-fluorobenzylidene)-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione; C13H11FN2O3." Zeitschrift für Kristallographie - New Crystal Structures 231, no. 4 (December 1, 2016): 1059–61. http://dx.doi.org/10.1515/ncrs-2016-0050.

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AbstractC13H11FN2O3, triclinic, P1̅, a = 5.7471(4) Å, b = 7.8734(6) Å, c = 13.3112(11) Å, α = 75.546(3)°, β = 78.183(3)°, γ = 77.540(3)°, V = 562.22(7) Å3, Z = 2, Rgt(F) = 0.0444, wRref(F2) = 0.1234, T = 100 K.

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35

Fun, Hoong-Kun, Jeannie Bee-Jan Teh, Yun Liu, and Jian-Hua Xu. "3,3-Dimethyl-5-phenyl-3,4-dihydro-1H-benzo[b]carbazole-1,6,11(2H,5H)-trione." Acta Crystallographica Section E Structure Reports Online 63, no. 7 (June 13, 2007): o3146. http://dx.doi.org/10.1107/s1600536807027213.

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36

Abaszadeh, Mehdi, Hassan Sheibani, and Kazem Saidi. "The Condensation of (Chlorocarbonyl)phenyl Ketene with Bisnucleophiles. Synthesis of 4-Hydroxy-5-phenylpyro-[2,3-c]pyrazol-6-ones and Formation of Pyrazolo[1,2-a]pyrazole-triones by Hydrogen Exchange in Unstable Mesoionic Compounds." Australian Journal of Chemistry 63, no. 1 (2010): 92. http://dx.doi.org/10.1071/ch09344.

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The addition of (chlorocarbonyl)phenyl ketene 2 to 5-alkylpyrazol-3(4H)-ones 1 led to the formation of 3-hydroxypyrazolo[1,2-a]pyrazole-dione/pyrazolo[1,2-a]pyrazole-trione derivatives 3. This is ascribed to hydrogen exchange in initially formed unstable, mesoionic pyrazolo[1,2-a]pyrazol-4-ium-5-olates. In contrast, condensation of the same ketene with 3-alkyl-1-phenyl-2-pyrazolin-5-ones 4 afforded 4-hydroxy-3-alkyl-1,5-diphenylpyrano[2,3-c]pyrazol-6-one derivatives 5. The latter reaction provides a new and rapid route to 4-hydroxy-2-pyrones fused to pyrazole rings, in good to excellent yields.

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37

Shirini, Farhad, and Fatemeh Kamali. "Fe3O4/g-C3N4 Nanocomposites as a Reusable Catalyst for the Synthesis of 5-Arylidenepyrimidine-2,4,6-(1H,3H,5H)-Trione and Pyrano-Pyrimidinone Derivatives in Aqueous Media." Journal of Nanoscience and Nanotechnology 20, no. 9 (September 1, 2020): 5433–44. http://dx.doi.org/10.1166/jnn.2020.17863.

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A green magnetic nanocatalyst is developed by immobilization of Fe3O4 on Graphitic carbon nitride (g-C3N4) support for the efficacious synthesis of 5-arylidenepyrimidine-2,4,6-(1H,3H,5H)-trione and pyrano-pyrimidinone derivatives in aqueous media. The most momentous features of the present protocol are the simple preparation of the catalyst, mild reaction conditions, short reaction times and high yields of the products. Moreover, the magnetic nanocatalyst Fe3O4/g-C3N4 can be recycled effectively and reused several times, without a significant loss in reactivity.

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38

Black, DS, N. Chaichit, BM Gatehouse, and GI Moss. "Unusual Formation of New Indole-Containing Heterocyclic Ring Systems." Australian Journal of Chemistry 40, no. 12 (1987): 1965. http://dx.doi.org/10.1071/ch9871965.

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The oxazinoindoletrione (3) underwent reaction with aqueous ammonia in methanol or ethanol to yield the polycyclic methyl or ethyl esters (4) and (5) respectively. Reaction of trione (3) with gaseous ammonia in dry ethanol gave the aminobenzodiazepinone (7). This compound lost ammonia on heating in toluene to give compound (11) and in the presence of methanol or ethanol gave the methyl or ethyl esters (9) and (10) respectively. The structures of compounds (4), (7) and (10) were all established by X-ray crystallography.

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39

Barakat, Assem, Abdullah M. Al-Majid, Hany J. Al-Najjar, M. Iqbal Choudhary, and Sammer Yousuf. "Crystal structure of 1,3-dimethyl-5-(2,4,6-trimethylbenzylidene)pyrimidine- 2,4,6-1H,3H,5H)-trione, C16H18N2O3." Zeitschrift für Kristallographie - New Crystal Structures 229, no. 4 (December 1, 2014): 269–70. http://dx.doi.org/10.1515/ncrs-2014-0128.

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40

Fun, Hoong-Kun, Suchada Chantrapromma, Yun Liu, and Jian-Hua Xu. "5-(4-Methoxyphenyl)-3,3-dimethyl-2,3,4,5-tetrahydro-1H-benzo[b]carbazole-1,6,11-trione chloroform solvate." Acta Crystallographica Section E Structure Reports Online 63, no. 7 (June 15, 2007): o3236—o3237. http://dx.doi.org/10.1107/s1600536807028334.

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41

Nirmala, S., K. Karthikeyan, E. Theboral Sugi Kamala, L. Sudha, and P. T. Perumal. "4′-(4-Methoxyphenyl)-1,1′,1′′-trimethyldispiro[indoline-3,2′-pyrrolidine-3′,3′′-pyrrolidine]-2,2′′,5′′-trione." Acta Crystallographica Section E Structure Reports Online 65, no. 7 (June 20, 2009): o1655—o1656. http://dx.doi.org/10.1107/s1600536809021114.

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42

Gryl, Marlena, and Katarzyna Stadnicka. "Rubidium 2,4,6-trioxo-1,3-diazinan-5-ide–1,3-diazinane-2,4,6-trione–water (1/1/1)." Acta Crystallographica Section E Structure Reports Online 67, no. 5 (April 13, 2011): m571—m572. http://dx.doi.org/10.1107/s1600536811012657.

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43

Rozek, Tomas, Wit Janowski, John M. Hevko, Edward R. T. Tiekink, Suresh Dua, David J. M. Stone, and John H. Bowie. "Syntheses of Angucyclinones Related to Ochromycinone." Australian Journal of Chemistry 51, no. 6 (1998): 515. http://dx.doi.org/10.1071/c97151.

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Two synthetic approaches have been investigated for the syntheses of model angucyclinones related to ochromycinone. The first involves a Diels–Alder/Friedel–Crafts strategy in which the Diels–Alder adduct formed between dimethyl acetylenedicarboxylate and 3-ethenyl-5,5-dimethylcyclohex-2-en-1- one was converted into 6,6-dimethyl-8-oxo-5,6,7,8-tetrahydronaphthalene-1,2-dicarboxylic anhydride, which was then reacted with benzene in a Friedel–Crafts reaction. Acid-catalysed cyclization of the Friedel–Crafts products gave 3,3-dimethyl-3,4-dihydrobenz[a]anthracene-1,7,12(2H)-trione (3) in poor yield. Angucyclinones related to (3) are formed (in 40–50% overall yield) by aromatization of the adduct formed between the appropriate 1,4-naphthoquinone and 3-[(E)-2-methoxyethenyl]- 5,5-dimethylcyclohex-2-en-1-one (this dienone reacts with itself by a Diels–Alder process to yield an adduct which decomposes to 3,3,8,8-tetramethyl-3,4,7,8-tetrahydroanthracene-1,6(2H,5H)-dione). When the substituted 1,4-naphthoquinone is unsymmetrical, a boron triacetate assisted Diels–Alder reaction gives a single regioisomer (e.g. X-ray investigations indicate that 8-hydroxy-3,3-dimethyl-3,4-dihydrobenz[a]anthracene-1,7,12(2H)-trione is the product from 5-hydroxy-1,4-naphthoquinone). An X-ray structural study of the Diels–Alder adduct in the above reaction confirms the operation of an endo cyclization.

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44

Anholeti, Maria Carolina, Selma R. de Paiva, Maria Raquel Figueiredo, and Maria Auxiliadora C. Kaplan. "Chemosystematic aspects of polyisoprenylated benzophenones from the genus Clusia." Anais da Academia Brasileira de Ciências 87, no. 1 (March 2015): 289–301. http://dx.doi.org/10.1590/0001-3765201520140564.

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Benzophenone derivatives are special metabolites that arouse great scientific interest. The Clusiaceae family is known for producing large amounts of benzophenone derivatives with several isoprene residues on their structures, which are responsible for the observed complexity and structural variety in this class of substances, and also contribute to their biological activities. Clusia is an important genus belonging to Clusiaceae, with 55 different polyisoprenylated benzophenones identified so far. These substances were analyzed from biosynthetic and chemosystematic points of view, allowing the determination of characteristics regarding their production, accumulation and distribution within this genus. Polyisoprenylated benzophenones found in Clusiashowed a high prenylation degree, with 2 to 5 isoprene units and a greater occurrence in flowers and fruits. Section Cordylandra showed a very similar occurrence of 2,4,6-trihydroxybenzophenone derivatives and bicyclo[3.3.1]nonane-2,4,9-trione derivatives, the majority of them with 4 isoprene units. In section Anandrogyne there is a predominance of simple 2,4,6-trihydroxy-benzophenone derivatives, with 2 isoprene units, and in Chlamydoclusia predominates bicyclo[3.3.1]nonane-2,4,9-trione derivatives with 4 isoprene units. Although highly prenylated, these substances showed low oxidation indexes, which from an evolutionary perspective corroborates the fact that Clusiaceae is a family in transition, with some common aspects with both basal and derived botanical families.

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45

Findlay, John A., Guoqiang Li, and John A. Johnson. "Bioactive compounds from an endophytic fungus from eastern larch (Larixlaricina) needles." Canadian Journal of Chemistry 75, no. 6 (June 1, 1997): 716–19. http://dx.doi.org/10.1139/v97-086.

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The structures of two novel metabolites isolated from cultures of an unidentified endophytic fungus obtained from an eastern larch (Larixlaricina (Du Roi) K. Koch) needle were shown to be 8,1′,5′-trihydroxy-3′,4′dihydro-1′H-[2,4′]binaphthalenyl-1,4,2′-trione, 1, and 2-methyloctanoic acid 6-oxo-2-propenyl-3,6-dihydro-2H-pyran-3-yl ester, 2. Structures were determined by spectroscopic means. Compound 1 was toxic to spruce budworm (ChoristoneurafumiferanaClem.) larvae while 2 was active against Vibriosalmonicida, Pseudomonasaeruginosa, and Staphylococcusaureus. Keywords: insect toxin, Larixlaricina endophyte, antimicrobial, endophyte metabolite.

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46

Dehghanpour, Hamid Reza, Mohammad H. Mosslemin, and Razieh Mohebat. "Graphene Oxide: A Carbocatalyst for the One-Pot Multicomponent Synthesis of 5-Aryl-1H-Indeno[2’,1’:5,6]Pyrido[2,3-d]Pyrimidine-2,4,6(3H)-Trione." Journal of Chemical Research 42, no. 1 (January 2018): 35–39. http://dx.doi.org/10.3184/174751918x15161933697835.

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A simple, straightforward and efficient method is described for the synthesis of 5-aryl-1H-indeno[2’,1’:5,6]pyrido[2,3-d]pyrimidine-2,4,6(3H)-trione via one-pot multicomponent reaction of indane-1,3-dione, arylaldehydes and 6-aminopyrimidin-2,4(1H,3H)-dione in presence of catalytic amount of graphene oxide in water. Graphene oxide is a versatile carbocatalyst and this is the first report on its application in a pyrido[2,3-d]pyrimidine synthesis. Good yield, use of readily available starting materials, operational simplicity, easy work-up and eco-friendly re-usable catalyst are the key features of this protocol.

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47

Ardakani, Leili Shaker, Mohammad Hossein Mosslemin, and Bahareh Sadeghi. "ChemInform Abstract: Three-Component Reaction of Alkyl Isocyanide, Acetylenic Diesters and 5-Hydroxy-5-arylpyrimidine-2,4,6(1H,3H,5H)-trione." ChemInform 47, no. 5 (January 2016): no. http://dx.doi.org/10.1002/chin.201605185.

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48

Ramm, M., B. Schulz, J. U. Thurner, and M. Ulbricht. "Crystal and molecular structure of 5-diazo-2,2-dimethyl-4,6-dioxo-1,3-dioxane and 5-diazo-1,3-dimethylpyrimidin-2,4,6-trione." Crystal Research and Technology 25, no. 3 (March 1990): 297–303. http://dx.doi.org/10.1002/crat.2170250312.

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49

Gelbrich, Thomas, and Ulrich J. Griesser. "Crystal structure of the α-racemate of methohexital." Acta Crystallographica Section E Crystallographic Communications 71, no. 2 (January 24, 2015): 206–9. http://dx.doi.org/10.1107/s205698901500105x.

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Molecules of the title compound, C14H18N2O3[systematic name: 5-allyl-5-(hex-3-yn-2-yl)-1-methylpyrimidine-2,4,6(1H,3H,5H)-trione in the (RbSh)/(SbRh) racemic form], are connected by mutual N—H...O=C hydrogen bonds in which the carbonyl group at the 2-position of the pyrimidinetrione ring is employed. These interactions result in an inversion dimer which displays a centralR22(8) ring motif. This dimer is topologically distinct from that of the previously reported (SbRh) form, which is, however, also based on anR22(8) motif. The methyl group at the 1-position of the pyrimidinetrione ring in the title structure is disordered over two sets of sites in a 0.57 (2):0.43 (2) ratio.

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50

Rozek, Tomas, Tomas Rozek, Dennis K. Taylor, Dennis K. Taylor, Edward R. T. Tiekink, Edward R. T. Tiekink, John H. Bowie, and John H. Bowie. "Syntheses of Angucyclinones Related to Ochromycinone. III. An 11-Hydroxy Isomer and Some Reduced Analogues." Australian Journal of Chemistry 52, no. 2 (1999): 129. http://dx.doi.org/10.1071/c98124.

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The boron triacetate assisted Diels Alder reaction between racemic 5,5-dimethyl-3-vinylcyclohex- 2-enyl acetate and 5-hydroxynaphthoquinone yields the racemic 11-hydroxy-3,3-dimethyl-7,12-dioxo- 1,2,3,4,6,6a,7,12,12a,12b-decahydrobenzo[a]anthracen-1-yl acetate as the sole stereoisomer by regio- and stereo-selective cis endo addition. Aromatization of the Diels Alder adduct followed by hydrolysis of the acetate and oxidation of the resultant 1-hydroxy group gives the target angucyclinone, 11-hydroxy-3,3-dimethyl-1,2,3,4,7,12-hexahydrobenzo[a]anthracene-1,7,12-trione, in an overall yield of 37% from 5-hydroxynaphthoquinone. The regio- and stereo-selectivity of the Diels Alder addition is confirmed by a combination of 13C n.m.r. spectroscopy and X-ray crystallography.

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