2- 2 -Hydroxyimino-2 -

Typical preparations have been described for 2-(r-hydroxyiminomethyl)pyrazine (138) 2-(4 -dimethylamino-T-hydroxyiminobutyl)pyrazine (1186) 2-(2 -hydroxy-iminopentyl)-6-methylpyrazine (645) 2-(2 -hydroxyimino-3, 3 -dimethylbutyl)-6-methylpyrazine (645) 2-[r-hydroxyimino-2-(pyridin-2"-yl) (hyl]pyrazine (642) 2-[2 -hydroxyimino-2 -(pyridin-2"-yl, pyrazin-2"-yl, or pyrimidin-4 -yl)ethyl]pyrazine (642) 2-[l, 2 -bishydroxyimino-2 -(pyridin-2"-yl)ethyl]pyrazine (642) 2-12 -(2",4"-dinitrophenylhydrazono)-3 -methylbutyl]-6-methylpyrazine (645) 2-[ 1-(substituted hydrazono)ethyl]pyrazine (1196) 2-[l -phenyl-1 -(substituted hydrazono)methyl]-pyrazine (1196) 2-(r-thiosemicarbazonoethyl)pyrazine (138) 2-(2 -chloro-l -thiosemicarbazonoethyOpyrazine (138) and 2,5-dimethyl-3,6-bis(r-semicarbazono-ethyl)pyrazine (1196). 

For oximes, the word oxime is placed after the name of the aldehyde or ketone. If the carbonyl group is not the principal group, use the prefix hydroxyimino-. Compounds with the group Z = N—OR are named by a prefix alkyloxyimino- as oxime O-ethers or as O-substituted oximes. Compounds with the group r C=N(0)R are named by adding A-oxide after the name of the alkylideneaminc compound. For amine oxides, add the word oxide after the name of the base, with locants. For example, C5H5N—O is named pyridine A-oxide or pyridine 1-oxide. 

A -benzyl or W-propyl-/V-nitrosohydrazir es 28a,b at 50 C for 6 days ot nitrosated to ethyl 2-(hydroxyimino)-3-oxobutanoate 29 which was then heated with benzyl-hydrazine 30a OT n-propylhydrazine 30b in ethanol (87JOU1773) (Scheme 8). 

Substituted perhydropyrido[l,2-n]pyrazines were reacted with 2-fluorobenzohydroximinoyl chlorides in the presence of DBU in CHCI3 to yield a isomeric mixture of 7-substituted 2-[(hydroxyimino)phenylmethyl]-perhydropyrido[l, 2-u]pyrazines (99MIP9). 

Benzo[i/]isoxazol-3-yl)perhydropyrido[ 1,2-u]pyrazines were obtained by the cyclization of 2-[(hydroxyimino)phenylmethyl]pyrido[l,2-u]pyrazines on the action of NaH in THF at 90 °C for 18 h (99MIP9). 

Chemical Name 1 -([4-[1 -(Hydroxyimino)ethyll phenoxy] acetyl] piperidine Common Name N-(p-1 -NitrosoethyOphenoxyacetylpiperidine, pifoxime Structural Formula /--- ... 

Therapeutic Function Cholinesterase reactivator (antidote for nerve gas) Chemical Name 2-[(Hydroxyimino)methyl] -1-methylpyridinium chloride Common Name 2-PAM chloride Structural Formula ... 

It was claimed3 that heating the oxime 2-[2-(hydroxyimino)propanyl]benzoic acid above its melting point resulted in dehydration to give 4-methyl-2,3-benzoxazepin-l(5//)-one (2, R = Me), as orange-red needles,4 but the color of the compound indicates that it has a different structure. 

It should be noted that fibres with high heat resistance can be also obtained by treating modified fibres of type 6, containing hydroxyimino groups, with Fe3 and Ni2+ salts, which is again explained by the formation of intermolecular chemical bonds. 

A-(2-Hydroxyimino-l,2-diphenylethylidene)aniline (13) gave 2,3-diphenylqui-noxahne (12) [neat AC2O, reflux, <24 h [monitored by thin-layer chromatography (tic)] 57% via the isolable acetoxyimino intermediate by a radical mechanism] or 2,3-diphenylquinoxaline 1-oxide (14) [Pb(OAc)4, CH2CI2, 25°C, 1 h 48%] when unsymmetric aniline substrates were used, two... 

Benzenediamine (148) and frani-l-chloro-l,2-bis(hydroxyimino)ethane (149) gave 2(177)-quinoxalinone oxime (150), perhaps better formulated as 2-hydroxyaminoquinoxaline (151) (EtOH, 20°C, 3 h 71%) 6,7-dibromo-l,2-benzenediamine likewise gave 6,7-dibromo-2-hydroxyamino-quinoxaline. ... 

Note There is considerale variety in this category, including, for example, the use of hydroxyimino- or nitroso derivatives of benzene as substrates. 

Likewise, 2-hydroxyimino-4-methylcyclohexanone (305) and the same synthon (303) gave 3-amino-6-methyl-5,6,7,8-tetrahydro-2-quinoxalinecarbonitrile 4-oxide (306) (Pr OH, 20°C, 48 h 74%). ... 

The extranuclear C-nitrosoquinoxalines are typified by 3-(a-methoxycarbonyl-a-nitrosomethyl)-2(l/i)-quinoxalmone (66), made by nitrosation of 3-(methoxy-carbonylmethyl)-2(l/f)-quinoxalmone (65) [AcOH, CI3CO2H, C5H11ONO, 20°C, 3 h 91% spectra suggest that the hydroxyimino tautomer (67) may predominate] and was subsequently reduced to afford 3-(a-amino-a-methoxycarbonylmethyl)-2(l//)-quinoxafinone (68) (PtOa, H2, 1 atm, THF, EtOH, 20°C, 4 h 59%) also by 3-[a-(4-amino-5-methyl-4//-l,2,4-triazol-3-yl)-a-nitrosomethyl]-2(l//)-quinoxa-linone (69, R = NO), prepared by nitrosation of 3-(4-amino-5-methyl-4//-1,2,4-triazol-3-ylmethyl)-2(177)-quinoxalinone (69, R = H) [NaN02 ( 1.25 equiv), AcOH, H2O, no further details 79%]." ... 

Hydroxyimino)ethyl]quinoxaline (112) gave 2-(l-cyano-2-dimethylami-... 

Hydroxyimino)methyl]amino-3-methylquinoxahne (193) (considered here as the oxime of an aldehyde) gave 4-methyl[l,2,4]triazolo[l,5-u]quinoxaline (194) (polyphosphoric acid, 75°C, 7 h 66%). ... 

Note. Such derivatives of quinoxaline ketones are not encountered as often as those of quinoxalinecarbaldehydes, but a few examples can be given here. 6-Acetyl-2-phenylquinoxaline gave its oxime, 6-[l-(hydroxyimino)ethyl]-2-phe-nylquinoxaline (209) (H2NOH HCl, NaOH, EtOH, H2O, reflux, 2 h 75%). ... 

The ketoxime, 3-[ot-hydroxyimino-a-(5-methyl-l,2,4-tiiazol-3-yhnethyl)]-2(17/)-quinoxalinone (218), gave 3-(5-methyl-l,2,4-triazol-3-yl)isoxazolo[4,5-7>]-quinoxaline (219) (POCI3, dioxane, reflux, h 88%)." ... 

CN l,r-[oxybis(methylene)]bis[4-[(hydroxyimino)methyl]pyridinium] dichloride... 

Ci,HijNOjS i55//-f5-0) see Meloxicam methyl 4-(2-hydroxyethoxy)benzoate (C],)H 204 3204-73-7) see Raloxifene hydrochloride methyl A -(2-hydroxyethyl)dithiocarbamate (CjHijNOSi 56158-48-6) see Flomoxef A -methyl-At-(2-hydroxyethyl)guanidine phosphate (C4H,4Nj05P 33018-83-6) see Creatinolfosfate 5-methyl-10-hydroxyimino-10,ll-dihydro-5H-dibenz-[6/lazepine... 

Cieplak apphed this effect to the explanation of the shift of selectivity in the reactions of the pentamethylcyclopentadienes 21,19, and 20 having substiments of formyl, vinyl, and (hydroxyimino)methyl moiety at the 5-positions [14]. He pointed out that the observed result is consistent with the notion that in the case of formyl moiety the hyperconjugative effect is enhanced by lone pair back-donation due to ... 

Other Alkoxycarbonylating Reagents Prepared from 2-Hydroxyimino-2-phenylacetonitrile... 

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