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Journal articles on the topic 'Benzoxazinones'

Author: Grafiati

Published: 4 June 2021

Last updated: 1 February 2022

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1

Silva, Herman, Sylvia V. Copaja, Héctor R. Bravo, and Victor H. Argandoña. "Relationship between Grain Yield, Osmotic Adjustment and Benzoxazinone Content in Triticum aestivum L. Cultivars." Zeitschrift für Naturforschung C 61, no. 9-10 (October 1, 2006): 704–8. http://dx.doi.org/10.1515/znc-2006-9-1016.

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AbstractFifteen wheat genotypes were grown under water deficit to ascertain the role of osmotic adjustment (OA) and the concentration of benzoxazinones in sustaining grain yield. A positive correlation between osmotic adjustment capacity and yield was observed in wheat genotypes cultivated under field conditions. The weight gain of plants exposed to drought was in agreement with the OA values (R2 = 0.93). However, when wheat plants were infested by cereal aphids, this correlation was not found. The benzoxazinones 2,4-dihydroxy-1,4-benzoxazin- 3-one (DIBOA) and 2,4-dihydroxy-7-methoxy-1,4 benzoxazin-3-one (DIMBOA) are defensive secondary metabolites present in wheat and others cereals. The content of these compounds varied in wheat genotypes and increased with drought and aphid infestation. A positive correlation between weight gain of irrigated-infested plants and drought-infested plants and the contents of benzoxazinones was observed. These results suggest that plants with better OA capacity and high benzoxazinone content should have better field yields.

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2

Bücker, Claudia, and Hans J. Grambow. "Alterations in 1,4-Benzoxazinone Levels Following Inoculation with Stem Rust in Wheat Leaves Carrying Various Alleles for Resistance and Their Possible Role as Phytoalexins in Moderately Resistant Leaves." Zeitschrift für Naturforschung C 45, no. 11-12 (December 1, 1990): 1151–55. http://dx.doi.org/10.1515/znc-1990-11-1211.

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The contents of 1,4-benzoxazinone derivatives in wheat plants infected with Puccinia graminis Pers. f. sp. tritici Ericss. & Henn, race 32, and in uninfected controls were examined in four near-isogenic lines of different infection types: Triticum aestivum L., cultivar Prelude Sr5 (highly resistant), Sr24, Sr26 (moderately resistant), and srx (susceptible). In all infection types the contents of DIMBOA -glc and HMBOA -glc decrease with time in the uninfected controls as well as in the infected plants. However, following inoculation, the synthesis of HDIBOA -glc is drastically increased in the moderately resistant cultivars. The results suggest that this fully methylated 1,4-benzoxazinone may function as a phytoalexin in this type of interaction. The benzoxazolinone MBOA which has been described as an in vitro conversion product of the benzoxazinones mentioned above is not detected in inoculated or uninoculated leaves.

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3

Huo, Chang-Hong, Bin Wang, Wen-Han Lin, and Yu-Ying Zhao. "Benzoxazinones from Acanthus ilicifolius." Biochemical Systematics and Ecology 33, no. 6 (June 2005): 643–45. http://dx.doi.org/10.1016/j.bse.2004.11.002.

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4

Marcacci, Sylvie, Muriel Raveton, Patrick Ravanel, and Jean-Paul Schwitzguébel. "The Possible Role of Hydroxylation in the Detoxification of Atrazine in Mature Vetiver (Chrysopogon zizanioides Nash) Grown in Hydroponics." Zeitschrift für Naturforschung C 60, no. 5-6 (June 1, 2005): 427–34. http://dx.doi.org/10.1515/znc-2005-5-611.

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The resistance mechanism of vetiver (Chrysopogon zizanioides) to atrazine was investigated to evaluate its potential for phytoremediation of environment contaminated with the herbicide. Plants known to metabolise atrazine rely on hydroxylation mediated by benzoxazinones, conjugation catalyzed by glutathione-S-transferases and dealkylation probably mediated by cytochromes P450. All three possibilities were explored in mature vetiver grown in hydroponics during this research project. Here we report on the chemical role of benzoxazinones in the transformation of atrazine.Fresh vetiver roots and leaves were cut to extract and study their content in benzoxazinones known to hydroxylate atrazine, such as 2,4-dihydroxy-2H-1,4-benzoxazin-3(4H)- one (DIBOA), 2,4-dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one (DIMBOA) and their mono- and di-glucosylated forms. Identification of benzoxazinones was performed by thin layer chromatography (TLC) and comparison of retention factors (Rf) and UV spectra with standards: although some products exhibited the same Rf as standards, UV spectra were different. Furthermore, in vitro hydroxylation of atrazine could not be detected in the presence of vetiver extracts. Finally, vetiver organs exposed to [14C]-atrazine did not produce any significant amount of hydroxylated products, such as hydroxyatrazine (HATR), hydroxydeethylatrazine (HDEA), and hydroxy-deisopropylatrazine (HDIA). Altogether, these metabolic features suggest that hydroxylation was not a major metabolic pathway of atrazine in vetiver.

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5

Lang, Ming, and Jian Wang. "A carbene-catalyzed tandem isomerization/cyclisation strategy: an efficient assembly of benzoxazinones." Organic Chemistry Frontiers 6, no. 9 (2019): 1367–71. http://dx.doi.org/10.1039/c9qo00094a.

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6

Martinand-Lurin, E., A. Dos Santos, L. El Kaim, L. Grimaud, and P. Retailleau. "Double Smiles rearrangement of Passerini adducts towards benzoxazinones." Chem. Commun. 50, no. 17 (2014): 2214–17. http://dx.doi.org/10.1039/c3cc49022j.

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7

Yoshida, H., A. Kunai, H. Fukushima, and J. Ohshita. "Benzyne-Mediated Route to Benzoxazinones." Synfacts 2006, no. 12 (December 2006): 1221. http://dx.doi.org/10.1055/s-2006-955575.

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8

Friebe, Annette. "Role of Benzoxazinones in Cereals." Journal of Crop Production 4, no. 2 (June 2001): 379–400. http://dx.doi.org/10.1300/j144v04n02_18.

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9

Cimarelli, Cristina, Gianni Palmieri, and Emanuela Volpini. "A facile synthesis of 3,4-dialkyl-3,4-dihydro-2H-1,3-benzoxazin-2-ones and naphthoxazin-2-ones and their reactions with organolithium and Grignard reagents Preparation of N-[1-(2′-hydroxyphenyl)alkyl]amides." Canadian Journal of Chemistry 82, no. 8 (August 1, 2004): 1314–21. http://dx.doi.org/10.1139/v04-100.

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A facile and simple method for the preparation of 3,4-dialkyl-3,4-dihydro-2H-1,3-benzoxazin-2-ones or naphthoxazin-2-ones in high yields from aminoalkylphenols and aminoalkylnaphthols is described. The reactions of the products obtained with organolithium and Grignard reagents were studied, and a method for the preparation of N-[1-(2-hydroxyphenyl)alkyl]-N-alkylamides, which are of pharmaceutical interest, from benzoxazinones was developed. A possible reaction mechanism is also proposed. The relative configuration of chiral products was determined from conformational analysis of 1H NMR spectra.Key words: benzoxazinones, naphthoxazinones, organometallic reagents, amide preparation, aminoalkylphenols.

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10

Li, Jinbiao, Shuaizhong Zhang, Madhava Reddy Lonka, Jinquan Zhang, and Hongbin Zou. "Rhodium(iii)-catalyzed cascade reactions of benzoic acids with dioxazolones: discovery of 2,5-substituted benzoxazinones as AIE molecules." Chemical Communications 55, no. 75 (2019): 11203–6. http://dx.doi.org/10.1039/c9cc05178c.

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11

Huo, Congde, Jie Dong, Yingpeng Su, Jing Tang, and Fengjuan Chen. "Iron-catalyzed oxidative sp3 carbon–hydrogen bond functionalization of 3,4-dihydro-1,4-benzoxazin-2-ones." Chemical Communications 52, no. 91 (2016): 13341–44. http://dx.doi.org/10.1039/c6cc05885j.

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12

Zhang, Xu, Bin Xu, and Ming-Hua Xu. "Rhodium-catalyzed asymmetric arylation of N- and O-containing cyclic aldimines: facile and efficient access to highly optically active 3,4-dihydrobenzo[1,4]oxazin-2-ones and dihydroquinoxalinones." Organic Chemistry Frontiers 3, no. 8 (2016): 944–48. http://dx.doi.org/10.1039/c6qo00191b.

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13

Rad-Moghadam, Kurosh, and Mehdi Mohseni. "An Expeditious and Solvent-Free Route to the Synthesis of 2-Substituted Quinazolin-4(3H)-Ones Under Microwave Conditions." Journal of Chemical Research 2003, no. 8 (August 2003): 487–88. http://dx.doi.org/10.3184/030823403103174632.

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14

Chen, Kaili, Biao Gao, Yanguo Shang, Jianyao Du, Qinlan Gu, and Jinxin Wang. "I2-Catalyzed cross dehydrogenative coupling: rapid access to benzoxazinones and quinazolinones." Org. Biomol. Chem. 15, no. 41 (2017): 8770–79. http://dx.doi.org/10.1039/c7ob02038d.

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15

Han, Zhengyu, Gang Liu, Rui Wang, Xiu-Qin Dong, and Xumu Zhang. "Highly efficient Ir-catalyzed asymmetric hydrogenation of benzoxazinones and derivatives with a Brønsted acid cocatalyst." Chemical Science 10, no. 15 (2019): 4328–33. http://dx.doi.org/10.1039/c8sc05797d.

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The Ir-catalyzed highly efficient asymmetric hydrogenation of benzoxazinones and derivatives was successfully developed with N-methylated ZhaoPhos L5 as the ligand, affording various chiral dihydrobenzoxazinones and derivatives with excellent results.

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16

Sun, Meng, Xiao Wan, Si-Jia Zhou, Guang-Jian Mei, and Feng Shi. "Iridium and a Brønsted acid cooperatively catalyzed chemodivergent and stereoselective reactions of vinyl benzoxazinones with azlactones." Chemical Communications 55, no. 9 (2019): 1283–86. http://dx.doi.org/10.1039/c8cc08962k.

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Under cooperative catalysis of iridium and a Brønsted acid, different C4-substituted azlactones react with vinyl benzoxazinones via a formal [4+2] cycloaddition or substitution reaction in a chemo- and stereoselective mode.

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17

Zhao, Zi-Biao, Xiang Li, Mu-Wang Chen, Zongbao K. Zhao, and Yong-Gui Zhou. "Biomimetic asymmetric reduction of benzoxazinones and quinoxalinones using ureas as transfer catalysts." Chemical Communications 56, no. 53 (2020): 7309–12. http://dx.doi.org/10.1039/d0cc03091k.

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Using ureas as transfer catalysts through hydrogen bonding activation, biomimetic asymmetric reduction of benzoxazinones and quinoxalinones has been developed, giving chiral products with high enantioselectivities. A key dihydroquinoxalinone intermediate of a BRD4 inhibitor was synthesized using biomimetic asymmetric reduction.

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18

Macías, Francisco A., Nuria Chinchilla, Elena Arroyo, José M. G. Molinillo, David Marín, and Rosa M. Varela. "Combined Strategy for Phytotoxicity Enhancement of Benzoxazinones." Journal of Agricultural and Food Chemistry 58, no. 3 (February 10, 2010): 2047–53. http://dx.doi.org/10.1021/jf903445m.

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19

Jarvest, Richard L., Martin J. Parratt, Christine M. Debouck, Joselina G. Gorniak, L. John Jennings, Halina T. Serafinowska, and James E. Strickler. "Inhibition of HSV-1 protease by benzoxazinones." Bioorganic & Medicinal Chemistry Letters 6, no. 20 (October 1996): 2463–66. http://dx.doi.org/10.1016/0960-894x(96)00455-6.

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20

Dabiri, Minoo, Noushin Farajinia Lehi, Siyavash Kazemi Movahed, and Hamid Reza Khavasi. "Pd-Catalyzed regioselective C–H halogenation of quinazolinones and benzoxazinones." Organic & Biomolecular Chemistry 15, no. 29 (2017): 6264–68. http://dx.doi.org/10.1039/c7ob01534h.

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21

Arroyo, Elena, Nuria Chinchilla, José M. G. Molinillo, Francisco A. Macias, Antonio Astola, Manuela Ortiz, and Manuel M. Valdivia. "Aneugenic effects of benzoxazinones in cultured human cells." Mutation Research/Genetic Toxicology and Environmental Mutagenesis 695, no. 1-2 (January 2010): 81–86. http://dx.doi.org/10.1016/j.mrgentox.2009.12.006.

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22

Nagao, T. "Benzoxazinones from Coix lachryma-jobi var. ma-yuen." Phytochemistry 23, no. 12 (November 26, 1985): 2959–62. http://dx.doi.org/10.1016/s0031-9422(00)80613-5.

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23

Nagao, Tsuneatsu, Hideaki Otsuka, Hiroshi Kohda, Tomohiro Sato, and Kazuo Yamasaki. "Benzoxazinones from Coix lachryma-jobi var. ma-yuen." Phytochemistry 24, no. 12 (November 1985): 2959–62. http://dx.doi.org/10.1016/0031-9422(85)80035-2.

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24

Qi, Xinxin, Rui Li, Hao-Peng Li, Jin-Bao Peng, Jun Ying, and Xiao-Feng Wu. "Palladium-Catalyzed Carbonylative Synthesis of N -Acetyl Benzoxazinones." ChemCatChem 10, no. 16 (July 2, 2018): 3415–18. http://dx.doi.org/10.1002/cctc.201800532.

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25

Iwamura, Hajime, Eri Nakagawa, and Nobuhiro Hirai. "Localization of Benzoxazinones that Occur Constitutively in Wheat Seedlings." Zeitschrift für Naturforschung C 51, no. 11-12 (December 1, 1996): 807–12. http://dx.doi.org/10.1515/znc-1996-11-1207.

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Occurrence and localization of novel antimicrobial and antifeeding compounds in wheat, 2,4-dihydroxy-1,4-benzoxazin-3-one (DIBOA ) and 2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one (DIMBOA), and their glucosides, were examined by staining wheat plants ( Triticum aestivum L.) in the juvenile stage of growth by ferric chloride. The methanol extracts of the stained plant tissues gave a characteristic blue color, which was shown by spectroscopic and chromatographic analyses to be exclusively due to benzoxazinones. When ferric chloride was applied to the root in the seedlings, the blue color immediately developed, the staining being strongest at the tip region and becoming lighter towards the basal part. The staining pattern of the radicle in the pre-emerging seed was similar to that in the root, but the coleorhiza was not stained. Little staining was observed in the epidermal layer of the leaf sheath in the shoot but the underlying tissue was stained strongly. The foliage leaf folded in the sheath was also stained, but less intense than the sheath tissue. It is suggested that the DIBOA and DIMBOA are produced within the stained region of the leaf and root. Together with previous findings that the benzoxazinones appear constitutively in wheat during the juvenile stage of growth, their localized occurrence in the tissues exposed to microbial and insect attacks suggests that they act as defense compounds during this vulnerable plant stage.

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26

Karataş, Mert Olgun, Harun Uslu, Bülent Alıcı, Başak Gökçe, Nahit Gencer, and Oktay Arslan. "Some coumarins and benzoxazinones as potent paraoxonase 1 inhibitors." Journal of Enzyme Inhibition and Medicinal Chemistry 31, no. 6 (February 17, 2016): 1386–91. http://dx.doi.org/10.3109/14756366.2016.1142982.

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27

Etter, M. C., Z. U. Lipkowska, G. Precigoux, F. Leroy, C. Decoret, F. Bayard, J. Royer, and J. Vicens. "Reaction Gaz-Solide Organique. Hydrolyse De Benzoxazinones et Naphtoxazinones." Molecular Crystals and Liquid Crystals Incorporating Nonlinear Optics 161, no. 1 (August 1988): 67–76. http://dx.doi.org/10.1080/00268948808070240.

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28

Mohapatra, Debendra K., and Apurba Datta. "Efficient synthesis of biologically important chiral 2-alkylamino benzoxazinones." Bioorganic & Medicinal Chemistry Letters 7, no. 19 (October 1997): 2527–30. http://dx.doi.org/10.1016/s0960-894x(97)10010-5.

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29

Macías, Francisco A., David Marín, Alberto Oliveros-Bastidas, and José M. G. Molinillo. "Rediscovering the bioactivity and ecological role of 1,4-benzoxazinones." Natural Product Reports 26, no. 4 (2009): 478. http://dx.doi.org/10.1039/b700682a.

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30

Baravkar, Sachin B., Arup Roy, Rupesh L. Gawade, Vedavati G. Puranik, and Gangadhar J. Sanjayan. "Nucleophilic Ring-Opening of Benzoxazinones by DBU: Some Observations." Synthetic Communications 44, no. 20 (August 8, 2014): 2955–60. http://dx.doi.org/10.1080/00397911.2014.910529.

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31

Kröger, Denis, Torben Schlüter, Malte Fischer, Irina Geibel, and Jürgen Martens. "Three-Component Reaction toward Polyannulated Quinazolinones, Benzoxazinones, and Benzothiazinones." ACS Combinatorial Science 17, no. 3 (February 10, 2015): 202–7. http://dx.doi.org/10.1021/co500165a.

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32

Macías, Francisco A., João M. De Siqueira, Nuria Chinchilla, David Marín, Rosa M. Varela, and José M. G. Molinillo. "New Herbicide Models from Benzoxazinones: Aromatic Ring Functionalization Effects." Journal of Agricultural and Food Chemistry 54, no. 26 (December 2006): 9843–51. http://dx.doi.org/10.1021/jf062709g.

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33

Viji, Mayavan, Jaeuk Sim, Siyuan Li, Heesoon Lee, Kyungsoo Oh, and Jae-Kyung Jung. "Organocatalytic and Regiodivergent Mannich Reaction of Ketones with Benzoxazinones." Advanced Synthesis & Catalysis 360, no. 23 (October 8, 2018): 4464–69. http://dx.doi.org/10.1002/adsc.201800870.

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34

Himottu, Marja, Kalevi Pihlaja, Géza Stájer, and Pirjo Vainiotalo. "Electron-impact induced fragmentations of some quinazolinediones and benzoxazinones." Rapid Communications in Mass Spectrometry 7, no. 5 (May 1993): 374–77. http://dx.doi.org/10.1002/rcm.1290070512.

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35

Stephani, Ralph, Caterina Ferraro, and István Lengyel. "The Synthesis and Antimicrobial Evaluation of Some Spiro-Phthalidyl Benzoxazinones." HETEROCYCLES 84, no. 2 (2012): 1383. http://dx.doi.org/10.3987/com-11-s(p)99.

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36

Lu, Liang-Qiu, Yuehui Li, Kathrin Junge, and Matthias Beller. "Relay Iron/Chiral Brønsted Acid Catalysis: Enantioselective Hydrogenation of Benzoxazinones." Journal of the American Chemical Society 137, no. 7 (February 13, 2015): 2763–68. http://dx.doi.org/10.1021/jacs.5b00085.

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37

Lectka, T., J. Wolfer, T. Bekele, C. Abraham, and C. Dogo-Isonagie. "Highly Enantioselective Synthesis of 1,4-Benzoxazinones and α-Amino Acids." Synfacts 2007, no. 1 (January 2007): 0092. http://dx.doi.org/10.1055/s-2006-955660.

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38

Macías, Francisco A., David Marín, Alberto Oliveros-Bastidas, and José M. G. Molinillo. "Optimization of Benzoxazinones as Natural Herbicide Models by Lipophilicity Enhancement." Journal of Agricultural and Food Chemistry 54, no. 25 (December 2006): 9357–65. http://dx.doi.org/10.1021/jf062168v.

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39

Martinand-Lurin, E., A. Dos Santos, L. El Kaim, L. Grimaud, and P. Retailleau. "ChemInform Abstract: Double Smiles Rearrangement of Passerini Adducts Towards Benzoxazinones." ChemInform 45, no. 21 (May 8, 2014): no. http://dx.doi.org/10.1002/chin.201421190.

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40

Huang, Zhi-Zhen, and Liu-Sheng Zu. "RAPID N-ALKYLATION OF BENZOXAZINONES AND BENZOTHIAZINONES UNDER MICROWAVE IRRADIATION." Organic Preparations and Procedures International 28, no. 1 (February 1996): 121–23. http://dx.doi.org/10.1080/00304949609355917.

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41

Barnes, Jane P., and Alan R. Putnam. "Role of benzoxazinones in allelopathy by rye (Secale cereale L.)." Journal of Chemical Ecology 13, no. 4 (April 1987): 889–906. http://dx.doi.org/10.1007/bf01020168.

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42

Mueller, Rudolf, Yong-Xin Li, Aidan Hampson, Sheng Zhong, Clayton Harris, Christopher Marrs, Stanislaw Rachwal, Jolanta Ulas, Lena Nielsson, and Gary Rogers. "Benzoxazinones as potent positive allosteric AMPA receptor modulators: Part I." Bioorganic & Medicinal Chemistry Letters 21, no. 13 (July 2011): 3923–26. http://dx.doi.org/10.1016/j.bmcl.2011.05.026.

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43

Sharifi, Ali, Zahra Babaalian, M. Saeed Abaee, Maryam Moazami, and Mojtaba Mirzaei. "Synergistic promoting effect of ball milling and Fe(ii) catalysis for cross-dehydrogenative-coupling of 1,4-benzoxazinones with indoles." Heterocyclic Communications 27, no. 1 (January 1, 2021): 57–62. http://dx.doi.org/10.1515/hc-2020-0123.

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Abstract In this work, a novel C(sp3)–C(sp2) cross-dehydrogenative-coupling method is developed to react benzoxazin-2-one derivatives with various indoles. As a result, combined use of ball milling and Fe(ii) catalysis leads to rapid coupling of 1,4-benzoxazinones with derivatives of indole. Under the conditions, derivatives of 1 couple with various indoles at room temperature to produce good yields of the desired compounds within 0.5–2 h time period. Thus, derivatives of both starting materials couple smoothly under relatively mild conditions to give good yields of 3.

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44

Macías, Francisco A., David Marín, Alberto Oliveros-Bastidas, David Chinchilla, Ana M. Simonet, and José M. G. Molinillo. "Isolation and Synthesis of Allelochemicals from Gramineae: Benzoxazinones and Related Compounds." Journal of Agricultural and Food Chemistry 54, no. 4 (February 2006): 991–1000. http://dx.doi.org/10.1021/jf050896x.

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45

Lo Piparo, Elena, Martin Smiesko, Paolo Mazzatorta, Emilio Benfenati, Jacqueline Idinger, and Sylvia Blümel. "Preliminary Analysis of Toxicity of Benzoxazinones and Their Metabolites forFolsomia candida." Journal of Agricultural and Food Chemistry 54, no. 4 (February 2006): 1099–104. http://dx.doi.org/10.1021/jf050916v.

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46

Rybczynski, Philip J., Roxanne E. Zeck, Donald W. Combs, Ignatius Turchi, Thomas P. Burris, Jun Z. Xu, Maria Yang, and Keith T. Demarest. "Benzoxazinones as PPARγ agonists. part 1: SAR of three aromatic regions." Bioorganic & Medicinal Chemistry Letters 13, no. 14 (July 2003): 2359–62. http://dx.doi.org/10.1016/s0960-894x(03)00401-3.

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47

Singh, Chandrodai Pratap, Sumit Kumar, and Shailesh Kumar. "Aspects of Green Chemistry Towards Synthesis of Biologically Active Substituted Benzoxazinones." Advanced Science, Engineering and Medicine 10, no. 7 (July 1, 2018): 842–49. http://dx.doi.org/10.1166/asem.2018.2255.

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48

Partanen, Tuula, Pirjo Vainiotalo, Géza Stájer, and Gábor Bernáth. "Mass Spectrometric Fragmentation of Saturated Isoindolobenzoxazepinones and -benzoxazinones Under Electron Ionization." Rapid Communications in Mass Spectrometry 10, no. 9 (July 15, 1996): 1013–18. http://dx.doi.org/10.1002/(sici)1097-0231(19960715)10:9<1013::aid-rcm611>3.0.co;2-l.

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49

MOHAPATRA, D. K., and A. DATTA. "ChemInform Abstract: Efficient Synthesis of Biologically Important Chiral 2-Alkylamino Benzoxazinones." ChemInform 29, no. 3 (June 24, 2010): no. http://dx.doi.org/10.1002/chin.199803170.

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50

Ferraro, Caterina, Istvan Lengyel, and Ralph Stephani. "ChemInform Abstract: The Synthesis and Antimicrobial Evaluation of Some Spirophthalidyl Benzoxazinones." ChemInform 43, no. 22 (May 3, 2012): no. http://dx.doi.org/10.1002/chin.201222156.

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