Synthesis of some novel pyridine and naphthyridine derivatives

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we study the synthesis of several new pyridine derivatives.

Simple organic salts containing strong intermolecular H-bonds haveattracted anattention as materials which display ferroelectric-paraelectric phasetransitions (Fu et al.,2011a,b,c). With thepurpose of obtaining crystals of organic salts exhibiting ferroelectricphase transitions, various organic compounds have been studied and theseries of new materials have beenelaborated (Dai & Chen, 2011; Xu et al., 2011; Zheng,2011).Herewith we present the synthesis and crystal structure of the titlemolecular complex, pyridine-4-carbonitrile–oxalic acid (2/1).

List of Publications (1990年以降) 114

67. Scandium Triflate Catalyzed Formation of Benzothiazole from 2-Aminobenzothiol and Formaldehyde in the Presence of Water.
Itoh, T.; Nagata, K.; Miyazaki, M.; Ohsawa, A.
Heterocycles 2000, 52, 1037-1040.66. A Novel Synthesis of Chiral 1-Allyl-1,2,3,4-tetrahydro-β-carbolineEmploying Allyltributyltin and Chiral AcylChlorides.
Itoh, T.; Matsuya, Y.; Enomoto, Y.; Nagata, K.; Miyazaki, M.; Ohsawa, A. , 1999, 1799-1801.

65. Disproportionation Reaction of DisulfidesPromoted by Nitric Oxide (NO) in the Presenceof Oxygen.
Itoh, T.; Tsutsumi, N.; Ohsawa, A.
19992161-2166.

64. A Nobel Synthesis of Chiral TetrahydroisoquinolinesEmploying Silyl Enol Ethers in the Presenceof Chiral Acyl Chlorides.
Itoh, I.; Nagata, K.; Miyazaki, M.; Ohsawa, A.
19991154-1156.
63. Reactions of Secondary and Tertiary Amines with Nitric Oxide in the Presence of Oxygen.
Itoh, T.; Matsuya, Y.; Maeta, H.; Miyazaki, M.; Nagata, K.; Ohsawa, A.
. 1999, , 819-823. 62. One Pot Reaction of Unstable -Acyl Quaternary Salt of Thiazoles or Imidazoles with Silyl Enol Ethers Formed .
Itoh, T.; Miyazaki, M.; Nagata, K.; Matsuya, Y.; Ohsawa, A.
1999, , 667-671.
61. Effect of Oxygen on the Reaction of Secondary Amines with Nitric Oxide.
Itoh, T.; Matsuya, Y.; Maeta, H.; Miyazaki, M.; Nagata, K.; Ohsawa, A.
1999, , 133-135.
60. Allylation of -Acyl Quaternary Salts of Azaaromatics with Allyltrimethylsilane in the Presence of Triflate Ion.
Itoh, T.; Miyazaki, M.; Nagata, K.; Ohsawa, A.
1998, , 67-71.
59. Vicarious Nucleophilic Substitution of Pyridazinium -Dicyanomethylides.
Itoh, T.; Matsuya, Y.; Nagata, K.; Miyazaki, M.; Tsutsumi, N.; Ohsawa, A.
, 1998, 1637-1641.58. Synthesis of 1,2-Dihydroisoquinolines by the Reaction of Isoquinoline with Allyltributyltin or Silyl Enol Ethers in the Presence of -Acylating Agents
Itoh, T.; Miyazaki, M.; Nagata, K.; Hasegawa, H.; Ohsawa, A.; Nakamura, K. T.
1998, , 125-128.

The oxalic acid (10 mmol), pyridine-4-carbonitrile (20 mmol) and ethanol (50 mL)were put into a 100mL flask. The mixture was stirred at 60°C for 2 h, andthen the precipitate was filtered off. Colourless crystals suitable for X-raydiffraction were obtained by slow evaporation of the solution.


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Acetamide derivatives and one pyridone derivative were prepared. The structure of the synthesized compounds was verified through elemental analyses,1H -NMR and13C- NMR, IR spectra. The NQO1 inducer activity of the synthesized compounds was evaluated using a quantitative bioassay in Hepa1c1c7 murine hepatoma cells. The acetamide derivatives showed weak activity, with the 3-ethylphenyl being more potent than the 2-ethylphenyl derivative. The pyridone derivative was inactive.