Organic compounds -- part of the class 532-570 series – Organic compounds – Nitrogen attached directly or indirectly to the purine ring...
Patent
1991-04-29
1994-03-15
Shah, Mukund J.
Organic compounds -- part of the class 532-570 series
Organic compounds
Nitrogen attached directly or indirectly to the purine ring...
558396, 558438, C07D24126
Patent
active
052947114
DESCRIPTION:
BRIEF SUMMARY
DESCRIPTION
1. Technical Field
This invention relates to 3,6-diamino-2,5-pyrazinedicarbonitrile which is a new pyrazine derivative having the formula [II] and its preparation methods. ##STR2##
The 3,6-diamino-2,5-pyrazinedicarbonitrile is a red crystal and yellowish green fluorescent substance. It can be applied as fluorescent dyestuff, light energy conversion material and also a useful intermediate to synthesize compounds including such as pteridine ring.
2. Background Art
Pyrazines are one of the most important heterocycles containing nitrogen. They are widely used for agricultural, pharmaceutical, cosmetic, polymeric chemicals and functional materials. Amino and cyano groups are especially important as the substituents, because of their potentiality to convert into other functional groups and to introduce various derivatives. Therefore, pyrazines substituted with both these groups are prospective starting materials.
Since diaminomaleonitrile (abbreviated as DAMN, hereafter) and its derivatives are commonly basic starting materials in technical fields, further development of simple synthetic process from DAMN to the useful pyrazines has been expected.
Pyrazine derivatives, substituted by both amino and cyano groups such as 6-amino-2,3,5-pyrazinetricarbonitrile, 5,6-diamino-2,3-pyrazinedicarbonitrile and 3,5-diamino-2,6-pyrazinedicarbonitrile etc., have been synthesized from DAMN or its homologues as the starting materials. (J. Org. Chem., 39, 1235 (1974) and Japanese Patent Application No. Sho 63-75909).
On the other hand, the example of the 3,6-diamino-2,5-pyrazinedicarbonitrile having symmetric structure was depicted in U.S. Pat. No. 3,674,749 as the starting material for polymers. However, the compound mentioned in the specification text was quite different from the one shown in the figure. Furthermore, in the description neither the physical properties, nor the method of preparation of these examples of use of the pyrazine carbonitrile have been confirmed.
DISCLOSURE OF INVENTION
2,3-diamino-3-(phenylthio)acrylonitrile (abbreviated as DAAN, hereafter), which is a related substance of DAMN, is readily derived from hydrogen cyanide and diphenyl disulfide. The inventors have noted the powerful emission of fluorescence in the course of the research on the synthesis of new heterocyclic compounds from DAAN, traced the fluorescent compound formed, identified it as 3,6-diamino-2,5-pyrazinedicarbonitrile and established a simple method of synthesizing the compound by further investigations.
Therefore, an object of the invention is the compound 3,6-diamino-2,5-pyrazinedicarbonitrile and its method of preparation particularly by the reaction of the compounds which are homologues of DAAN, represented formula [I], wherein R is aryl, alkyl, aralkyl or alkenyl and may be substituted. ##STR3##
BEST MODES FOR CARRYING OUT THE INVENTION
A detailed description of the invention follows.
The compounds of general formula [I] as starting materials are able to be readily synthesized by known methods as described in Patent WO 88/01264.
The compounds represented by general formula [I] are reacted under the condition of (a) in an acid solution or (b) in a solution of their acid salt solutions.
The reaction (a) is generally carried out in organic solvents or in mixed solvents of organic solvents and water in the presence of an acid or buffer solution for pH adjustment at 0.degree.-30.degree. C. for one to several hours under atmospheric pressure, with bubbling air if necessary. Hydrocarbons such as benzene, toluene and xylene; nitriles such as acetonitrile; halogenated hydrocarbons such as chloroform and dichloromethane; esters such as ethyl acetate; alcohols such as methanol and ethanol, ketones such as acetone and methyl ethyl ketone, ethers such as tetrahydrofuran, dioxane and 1,2-dimethoxyethane, dimethylformamide and dimethyl sulfoxide are applicable, or, these mixtures are also adoptable as the reaction solvents. Acidity of the reaction system, that is, pH should be kept at 1-5, and it is particularly desirable to
REFERENCES:
patent: 3674749 (1972-07-01), Craven
patent: 3763161 (1973-10-01), Hartter
patent: 3928351 (1975-12-01), Donald
Begland et al, J. Org. Chem. 39, p. 1235 (1974).
The Pyrazines by G. B. Barlin, vol. 41 of The Chemistry of Heterocyclic Compounds, pp. 35-36, 98, 126, 128, 129, 280 (1982).
Kojima Takakazu
Matsui Nobuo
Tazaki Seiji
Yagihara Tomio
Yanagisawa Atsushi
Bernhardt E.
Mason, Jr. Joseph C.
Nippon Soda Co. Ltd.
Oujevolk George B.
Shah Mukund J.
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