Retro-ene reaction I: Reaction of N-hydroxymethylsaccharin with benzoyl chlorides and alkyl halides

N-Benzoylsaccharins, N-(saccharinylmethyl) benzoates and N-alkylsaccharins were synthesized from N-hydroxymethylsaccharin and the corresponding benzoyl chlorides or alkyl halides under different conditions. The reaction mechanisms are also discussed.     

Retro-ene reactions IV. Alkylation of 4,5-dichloro-1-hydroxy-methylpyridazin-6-one with α,ω-dibromoalkanes or 4,5-dichloro-1 -(ω-bromoalkyl)pyridazin-6-ones

Alkylation of 4,5-dichloro-1-hydroxymethylpyridazin-6-one ( 1 ) with α,ω-dibromoalkanes 2 or ω-bromo-alkylpyridazin-6-ones 3 via a fragmentation of the retro-ene type under the two restricted conditions was investigated.     

Reaction of 4,5-dichloro-3-nitropyridazin-6-one with dimethylchloromethyleneammonium chloride

3,4,5-Trichloropyridazin-6-one, 3,4,5,6-tetrachloropyridzine and 4,5-dichloro-3-(N,N-dimethylamino)-pyridazin-6-one were synthesized from 4,5-dichloro-3-nitropyridazin-6-one and dimethylchloromethylene-ammonium chloride selectively.     

Reaction of 1,1-dichloro-1-nitrosoalkanes with acid chlorides and zinc

1,1-Dichloro-1-nitrosoalkanes, similar to -halocarbonyl compounds, react with acid chlorides and zinc to give O- acylated acylhydroximoyl chlorides.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 2, pp. 477–478, February, 1990     

Reaction of 1,1-dichloro-1-nitrosoalkanes with trivalent phosphorus acid chlorides

Conclusions 1,1-Dichloro-1-nitrosoalkanes react with trivalent phosphorus acid chlorides not containing a P-O ether bond in the presence of nucleophilic reagents (sulfur dioxide, ethanethiol) to produce phosphorylated alkylchloroformoximes. This is rationalized in terms of intermediate O-alkylchloroformiminoyldichlorophosphorane formation.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya., No. 9, pp. 2128–2132, September, 1988.     

Reaction of 1-chloromethyl-4,5-dichloropyridazin-6-one

Reaction of 1-chloromethyl-4,5-dichloropyridazin-6-one with some nucleophiles such as sodium methoxide, sodium azide, 2-mercaptopyrimidine and phenol gave 2, 3, 4, 7, 8 and 10 . 5-Chloro-4-phenoxypyridazin-6-one ( 10 ) was also synthesized from 8 through 9.     

Synthesis of 4,5-dichloro-1-(4,5-dichloropyridazin-3-yl)pyridazin-6-one

This paper presents the synthesis of 4,5-dichloro-1-(4,5-dichloropyridazin-3-yl)pyridazin-6-one from 4,5-dichloropyridazin-6-one.     

Retro-ene reactions. III. Alkylation of 4,5-dichloro-1-hydroxymethylpyridazin-6-ones: Synthesis of 4,5-dichloro-1-(ω-phthalimido and saccharin-2′-ylalkyl)pyridazin-6-ones

4,5-Dichloro-1-(ω-phthalimido and saccharinyl-2′-ylalkyl)pyridazin-6-ones were synthesized from 4,5-dichloro-1-hydroxymethylpyridazin-6-one and the corresponding N-(ω-haloalkyl)phthalimides and saccharins via a fragmentation of retro-ene type.     

Reaction of 1-vinylbenzotriazole with alkyl halides and dialkyl sulfates

Adducts of alkyl halides and dialkyl sulfates with 1-vinylbenzyltriazole were synthesized, and their IR and UV spectra were investigated. The nitrogen atom in the 3 position is the coordination center in these quaternary nitrogen salts.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1571–1574, November, 1972.     

Reaction of N-vinylimidazoles with alkyl halides

Quaternary salts of N-vinylimidazole and N-vinylbenzimidazole were synthesized. The structures of the products of quaternization of the N-vinylimidazoles were proved by IR and UV spectra. The distribution of the -electron density in the N-vinylimidazole molecules was obtained by quantum-chemical calculation.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 958–960, July, 1971.     

Reaction of α-cyanomethylazaheterocycles with α-halo carboxylic acid chlorides and anhydrides

-Cyanomethylazaheterocycles (I) are acylated by -halo carboxylic acid chlorides and anhydrides at the methylene carbon atom to give hetaryl-containing halo ketones.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1515–1517, November, 1977.     

Synthesis of functionalized dialkyl ketones from carboxylic acid derivatives and alkyl halides

Unsymmetrical dialkyl ketones can be directly prepared by the nickel-catalyzed reductive coupling of carboxylic acid chlorides or (2-pyridyl)thioesters with alkyl iodides or benzylic chlorides. A wide variety of functional groups are tolerated by this process, including common nitrogen protecting groups and C-B bonds. Even hindered ketones flanked by tertiary and secondary centers can be formed. The mechanism is proposed to involve the reaction of a (L)Ni(alkyl)(2) intermediate with the carboxylic acid derivative.     

Ketone formation via mild nickel-catalyzed reductive coupling of alkyl halides with aryl acid chlorides

The present work highlights unprecedented Ni-catalyzed reductive coupling of unactivated alkyl iodides with aryl acid chlorides to efficiently generate alkyl aryl ketones under mild conditions.     

Reaction of substituted 2- and 4-methylpyrimidines with aromatic carboxylic acid chlorides

The effect of substituants in methylpyrimidines on the reaction of the methyl groups with aromatic carboxylic acid chlorides in the presence of triethylamine was studied. It is shown that, depending on the character of the substituents, the reaction with the acid chlorides takes place at the methyl groups or at the ring nitrogen atoms.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 687–690, May, 1982.