Citation: Şevket Hakan Üngören, Emine Dilekoğlu, İ rfan Koca. Synthesis of pyrazine-2,3-dicarbonitrile and 1,2,4-triazine-5(4H)-one derivatives from furan-2,3-diones[J]. Chinese Chemical Letters, ;2013, 24(12): 1130-1133.
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The reaction of furan-2,3-diones with S-methylisothiosemicarbazide hydroiodide yielded novel 1,2,4- triazine-5(4H)-ones, and reaction of furan-2,3-diones with diaminomaleonitrile led to the formation of pyrazine-2,3-dicarbonitrile derivatives, and the hydrolysis of these products led to the formation of more new pyrazine-2,3-dicarbonitrile derivatives. These compounds are potential herbicides and pesticides.
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-
[1]
[1] J.A. Joule, K. Mills, Heterocyclic Chemistry, Blackwell, Oxford, 2000.
-
[2]
[2] S.B. Ferreira, C.R. Kaiser, Pyrazine derivatives: a patent review (2008 - present), Expert Opin. Ther. Pat. 22 (2012) 1033-1051.
-
[3]
[3] Y.B. Zhang, X.L. Wang, W. Liu, et al., Design, synthesis and biological evaluation of heterocyclic azoles derivatives containing pyrazine moiety as potential telomerase inhibitors, Bioorg. Med. Chem. 20 (2012) 6356-6365.
-
[4]
[4] Y. Suzuki, A. Suzuki, A. Tamaru, et al., Rapid detection of pyrazinamide-resistant mycobacterium tuberculosis by a PCR-based in vitro system, Clin. Microbiol. 40 (2002) 501-507.
-
[5]
[5] B. Milczarska, H. Foks, Z. Zwolska, Studies on pyrazine derivatives, XLIII: synthesis and antituberculosis activity of 6-(1,2,3,4-tetrahydroisoquinolino) and 6-(1,3,3- trimethyl-6-azabicyclo-[3,2,1]-octano)-pyrazinocarboxylic acid derivatives, Phosphorus, Sulfur Silicon Relat. Elem. 180 (2005) 2255-2264.
-
[6]
[6] M.H. Cynamon, R.J. Speirs, J.T. Welch, In vitro antimycobacterial activity of 5- chloropyrazinamide, Antimicrob. Agents Chemother. 42 (1998) 462-463.
-
[7]
[7] A. Nakamura, M. Ono, H. Segawa, et al., Studies on herbicidal 2,3-pyrazinedicarbonitriles (2,3-dicyanopyrazines). Part IV. Synthesis and herbicidal activity of 6- phenyl-5-propylamino-2-pyrazinecarbonitriles and related compounds, Agric. Biol. Chem. 48 (1984) 1009-1016.
-
[8]
[8] W. Heri, F. Pfister, B. Carroll, T. Parshley, J.B. Nabors, Production, development, and registration of triazine herbicides, in: Triazine Herbicides, 2008, 31-43.
-
[9]
[9] J. Jerzykiewicz, G. Klobus, The effect of triazine- and urea-type herbicides on photosynthetic apparatus in cucumber leaves, Acta Soc. Bot. Pol. 76 (2007) 43-47.
-
[10]
[10] J. Pitha, P. Fiedler, J. Gut Collect, Nucleic acid components and their analogs. LXXXII. The fine structure of 6-azaisocytosine and its derivatives, Czech. Chem. Commun. 31 (1966) 1864-1871.
-
[11]
[11] G. Kollenz, H. Sterk, G. Hutter, Mechanistic investigations aided by isotopic labeling. 10. Investigations of novel furan-2,3-dione rearrangements by oxygen- 17 labeling, J. Org. Chem. 56 (1991) 235-239.
-
[12]
[12] T. Hö kelek, E. Saripinar, İ. Yıldırım, et al., 4-(4-Methoxybenzoyl)-5-(4-methoxyphenyl)- 2,3-dihydro-2,3-furandione, Acta Crystallogr. E 58 (2002) 30-32.
-
[13]
[13] İ. Yıldırım, İ. Koca, Synthesis, characterization and some reactions of novel 4- aroyl-5-aryl-2,3-dihydro-2,3-furandiones, Kuwait, J. Sci. Eng. 32 (2005) 49-60.
-
[14]
[14] R.W. Saalfrank, T. Lutz, B. Hoerner, et al., 2,3-Dioxo-2,3-dihydrofurans. 2. Versatile synthesis of 2,3-dioxo-2,3-dihydrofurans and alkylidenebutenolides. Crystal and molecular structure of 5-(4-chlorophenyl)-4-methoxycarbonyl-2,3-dioxo-2,3- dihydrofuran, Chem. Ber. 124 (1991) 2289-2295.
-
[15]
[15] G.L. Sommen, A. Linden, H. Heimgartner, Selenium-containing heterocycles from isoselenocyanates: synthesis of 5-amino-2,4-dihydro-3H-1,2,4-triazole-3- selones, Helv. Chim. Acta 90 (2007) 641-651.
-
[16]
[16] D.D. Nekrasov, S.V. Koltsova, Y.S. Andreichikov, Reaction of 5-aryl-2,3-furandiones with some N- and C-substituted amino nitriles, Russ. J. Org. Chem. 31 (1995) 591-594.
-
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