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Pyrazinecarbonitrile oxides

This chapter includes not only nuclear and extranuclear pyrazinecarboxylic acids and anhydrides, but also the related esters, acyl halides, amides, hydrazides, nitriles, aldehydes, ketones, and any of their thio analogues a few rare isothiocyanatopy-razines and pyrazinecarbonitrile oxides are also included. To avoid repetition, interconversions of these pyrazine derivatives are discussed only at the first opportunity for example, the esterification of carboxylic acids is discussed as a reaction of carboxylic acids rather than as a preparative route to carboxylic esters, simply because the section on carboxylic acids precedes that on carboxylic esters. To minimize any confusion, many cross-references have been inserted. [Pg.299]

Pyrazinecarbonitrile Oxides are unstable but they can be generated from pyrazinecarbaldehyde oximes with TV-chlorosuccinimide and then trapped immediately by appropriate dipolarophiles to afford cyclic adducts, as illustrated in the following examples ... [Pg.346]

This process was undoubtedly developed for the manufacture of pyrazinamide (Zinamide, etc.),1696 a second-line drug for Mycobacterium tuberculosis infections, resistant to more effective and less toxic agents. Thus a mixture of 2-methyl-pyrazine (323), ammonia, oxygen, and steam is passed (at 400°C) over an alumina- or pumice-supported catalyst comprising one to three oxides of Ce, Cr, Mo, Mn, P, Sb, Ti, or (most importantly) V the main product (in up to 90% yield) is 2-pyrazinecarbonitrile (324), easily converted into 2-pyrazinecarboxamide... [Pg.128]

Bromo-5-methyl-2-pyrazinamine 4-oxide (187, R = Br) gave 3-amino-6-methyl-2-pyrazinecarbonitrile 1-oxide (187, R = CN) (CuCN, NaCN, Me2NCHO, 110°C, reflux, 4 h 59%).1508... [Pg.174]

Amino-6-dimethoxymethyl-2-pyrazinecarbonitrile from its 4-oxide (254) [neat (MeO)3P, reflux, N2, 4 h 68%].759,767... [Pg.232]

Dimethoxymethyl-3-dimethylaminomethyleneamino-2-pyrazinecarbonitrile 4-oxide (52) gave 3-amino-6-dimethoxymethyl-2-pyrazinecarbonitrile 4-oxide (53) [TsOH, (MeO)3CH, MeOH—H20, 20°C, 7 days 55%].759... [Pg.267]

All the major routes to pyrazinecarbonitriles have been discussed already by primary synthesis in Chapters 1 and 2 by cyanolysis of halogenopyrazines in Sections 4.2.8 and 4.4 by deoxidative cyanation of pyrazine N-oxides in Section 5.5.2.4 by the rare cyanolysis of nitropyrazines in Section 7.1.2 by cyanolysis of trimethylammoniopyrazine salts no recent examples by dehydration of pyrazinecarboxamides in Section 8.4.2 and by passenger introduction of a cyano group in a variety of ways, for example, by cyanoalkylation. [Pg.330]

In addition, l-benzyl-4-methyl-2-piperazinol (213) reacted with trimethylsilyl cyanide and boron trifluoride etherate to give l-benzyl-4-methyl-2-piperazinecar-bonitrile (214) (72% after separation from an isomer), which underwent partial dehydrogenation by m-chloroperoxybenzoic acid to afford 1 -benzyl-4-methyl-1,4,5,6-tetrahydro-2-pyrazinecarbonitrile (214a) in 53% yield 822 also, the oxime, 3-amino-6-hydroxyiminomethyl-2-pyrazinecarbonitrile 4-oxide (215) underwent... [Pg.330]

Acetamido-6-methyl-5-oxo-4,5-dihydro-2-pyrazinecarbonitrile 1-oxide 3-Acetamido-6-methyl-5-oxo-4,5-dihydro-2-pyrazinecarboxamide 2-Acetamidomethylpyrazine 2-Acetamido-5-methylpyrazine... [Pg.351]

Amino-6-ethoxymethyl-2-pyrazinecarbonitrile 3-Amino-6-ethoxymethyl-2-pyrazine-carbonitrile 4-oxide... [Pg.361]

Amino-4-hydroxy-5-oxo-4,5-dihydro-2-pyrazinecarbonitrile 3-Amino-5-(3-hydroxyprop-1 -enyl)-2-pyrazinecarbonitrile 4-oxide 3-Amino-5-(l-hydroxypropyl)-2-pyrazine-carbonitrile... [Pg.362]

Amino-6-methy]-2-pyrazinecarbonitrile 1 -oxide 3-Aniino-6-methyl-2-pyrazinecarbonitrile... [Pg.364]

Amino-5-phenyl-2-pyrazinecarbaldehyde 3-Amino-5-phenyl-2-pyrazinecarbonitrile 3-Amino-6-phenyl-2-pyrazinecarbonitrile 3-Amino-6-phenyl-2-pyrazinecarbonitrile 4-oxide 3-Amino-A-phenyl-2-pyrazinecarboxamide 3-Amino-5-phenyl-2-pyrazinecarboxamide 3-Amino-6-phenyl-2-pyrazinecarboxamide 3-Amino-6-phenyl-2-pyrazinecarboxamide 4-oxide... [Pg.364]

Amino-2-pyrazinecarbonitrile 3-Amino-2-pyrazinecarbonitrile 1,4-dioxide 3-Amino-2-pyrazinecarbonitrile 1 -oxide 3-Amino-2-pyrazinecarbonitrile 4-oxide 3-Amino-2-pyrazinecarbothioamide 3- Amino-2-pyrazinecarboxamide... [Pg.365]

Benzylthio-2-pyrazinecarbohydrazide 3-Benzylthio-2-pyrazinecarbonitrile 6-Benzylthio-2-pyrazinecarbonitrile 6-Benzylthio-2-pyrazinecarbothioamide 3-Benzylthio-2-pyrazinecarboxamide 6-Benzylthio-2-pyrazinecarboxamide 3-Benzylthio-2-pyrazinecarboxylic add 6-Benzylthio-2-pyrazinecarboxylic add 3-Benzylthi o-2,5-pyrazinedi carboxamide 2-Benzylthiopyrazine 4-oxide... [Pg.374]

Chloro-5,6-diphenyl-2-pyrazinecarbohydrazide 5-Chloro-3,6-diphenyl-2-pyrazinecarbonitrile 3-Chloro-5,6-diphenyl-2-pyrazinecarboxamide 2-Chloro-3,5-diphenylpyrazine 1 -oxide 2-Chloro-3,6-diphenylpyrazine 1-oxide 2-Chloro-3,6-diphenylpyrazine 4-oxide 2-Chloro-5,6-diphenylpyrazine 1-oxide... [Pg.387]

Dimethylamino-2-pyrazinecarbonitrile 6-Dimethylamino-2-pyrazinecarbonitrile 6-Dimethylamino-2-pyrazinecarboxamide 6-Dimethylamino-2-pyrazinecarboxylic acid 2-Dimethylaminopyrazine 1-oxide 2-Dimethylaminopyrazine 4-oxide 6-Dimethylamino-2,3,5-pyrazinetricarbonitrile 2-Dimethylamino-3,5,6-trifluoropyrazine 2-Dimethylamino-3,5,6-trimethylpyrazine Dimethyl 3,6-bis(methoxycarbonylmethyl)-... [Pg.410]

Ethoxy-3,6-dimethylpyrazine 5-Ethoxy-3,6-dimethyl-2-pyrazinecarbonitrile 5-Ethoxy-3,6-dimethyl-2-pyrazinecarbonitrile 1/4-oxide... [Pg.418]

Ethylthio-2-pyrazinecarbonitrile 6-Ethylthio-2-pyrazinecarbonitrile 6-Ethylthio-2-pyrazinecarbothioamide 3-Ethylthio-2-pyrazinecarboxamide 6-Ethylthio-2-pyrazinecarboxamide 3-Ethylthio-2-pyrazinecarboxylic acid 6-Ethylthio-2-pyrazinecarboxylic acid 3-Ethylthio-2,5-pyrazinedicarboxamide 2-Ethylthiopyrazine 1-oxide 2-Ethyl-3,5,6-trimethylpyrazine 2-Ethyl-3,5,6-triphenylpyrazine 2-Ethyl-3-vinylpyrazine 2-Ethynyl-3,6-dimethylpyrazine 2-Ethynyl-3-methylpyrazine 2-Fluoro-5,6-dimethoxy-3-methylpyrazine 2- Fluoro- 5,6-dimethoxypyrazine 2-Fluoro-3,6-dimethylpyrazine 2-Fluoro-3-(l-hydroxyethyl)pyrazine 2-Fluoro-3-iodopyrazine 2-Fluoromethyl-5-methyl-3,6-diphenylpyrazine 2- Fluoro- 5-phenylpyrazine 2-Fluoro-3-phenylthiopyrazine... [Pg.423]

Methoxy-6-phenyl-2-pyrazinecarbonitrile 2-Methoxy-3-phenylpyrazine 4-oxide 2-Methoxy-5-phenylpyrazine 4-oxide... [Pg.437]

Methyl-5,6-diphenyl-2-pyrazinecarbonitrile Methyl 5,6-diphenyl-2-pyrazinecarboxylate 2-Methyl-5,6-diphenylpyrazine 1-oxide... [Pg.445]

Thioxo-3,4-dihydro-2-pyrazinecarbonitrile 3-Thioxo-3,4-dihydro-2-pyrazinecarboxamide 6-Thioxo-1,6-dihydro-2-pyrazinecarboxamide 3-Thioxo-3,4-dihydro-2-pyrazinecarboxamide oxime 3-Thioxo-3,4-dihydro-2-pyrazinecarboxylic acid 6-Thioxo-1,6-dihydro-2-pyrazinecarboxylic acid 4-oxide... [Pg.459]

See other pages where Pyrazinecarbonitrile oxides is mentioned: [Pg.125]    [Pg.329]    [Pg.37]    [Pg.38]    [Pg.231]    [Pg.352]    [Pg.357]    [Pg.357]    [Pg.357]    [Pg.358]    [Pg.358]    [Pg.359]    [Pg.359]    [Pg.361]    [Pg.362]    [Pg.364]    [Pg.364]    [Pg.364]    [Pg.456]    [Pg.456]   
See also in sourсe #XX -- [ Pg.346 ]

See also in sourсe #XX -- [ Pg.346 ]



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3 - 2-pyrazinecarbonitrile

3-Amino-6-methyl-2-pyrazinecarbonitrile 1-oxide

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