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1.
Published information on methods for the production of benzazetines and their dehydro derivatives (benzazetes) and their chemical
transformations is reviewed and analyzed. It was noted that benzazetines with an unsubstituted NH group are unstable and their
stable representatives have only became accessible in recent years. The tendency of benzazetines to undergo opening of the
four-membered heterocycle and isomerization processes was demonstrated. The wide-ranging synthetic possibilities of benzazetines
and benzazetes are indicated.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1763–1783, December, 2007. 相似文献
2.
S. K. Petkevich V. I. Potkin R.V. Kaberdin 《Russian Journal of Organic Chemistry》2004,40(8):1146-1150
3-Aryl-5-methylenehydroxyiminoisoxazoles were synthesized by reaction of 1-aryl-3,4,4-trichloro-3-buten-1-ones with hydroxylamine. Reactions of ketones with hydrazine provided pyrazole structures; therewith two pyrazole molecules underwent coupling affording 3-arylpyrazole-5-carbaldehyde azines. 相似文献
3.
N. I. Nechai E. A. Dikusar V. I. Potkin R. V. Kaberdin 《Russian Journal of Organic Chemistry》2004,40(7):1009-1014
Previously unknown 4,5-dichloroisothiazole-3-carboxylic acid amides and esters were synthesized by reactions of 4,5-dichloroisothiazole-3-carbonyl chloride with ammonia, heterocyclic and aromatic amines, and functionally substituted alcohols and phenols. 相似文献
4.
Dikusar E. A. Potkin V. I. Vashkevich E. V. Kozlov N. G. Kaberdin R. V. 《Russian Journal of General Chemistry》2004,74(4):578-581
(Z)-2-Naphthylacetylene was synthesized by the reaction of (Z)-3-(2-naphthyl)-3-chloropropenal (prepared from 2-acetylnaphthalene) with aqueous NaOH in dioxane. The reactions of 2-naphthylacetylene with CuCl, [Ag(NH3)2]NO3, and K2[HgI4] gave copper, silver, and mercury 2-naphthylacetylenides, respectively. Silver naphthylacetylenide reacts with iodine to give the iodoethynyl derivative, which readily takes up bromine across the triple bond. 相似文献
5.
V. I. Potkin V. A. Knizhnikov A. A. Yanuchok R. V. Kaberdin 《Russian Journal of Organic Chemistry》2001,37(5):640-643
The reactions of 4-ethoxy-2-(2,3,3-trichloro-1-nitro-2-propenylidene)benzazetine with methyl- and phenyllithium at a ratio of 1:2 result in replacement of one chlorine atom and formation, respectively, of 4-ethoxy-2-(2,3-dichloro-3-methyl-1-nitro-2-propenylidene)benzazetine and 4-ethoxy-2-(2,3-dichloro-1-nitro-3-phenyl-2-propenylidene)benzazetine in 45 and 52% yield. With excess phenyllithium (reactant ratio 1:5), a mixture of products is formed due to replacement of one, two, and three chlorine atoms by phenyl groups. An analogous reaction with methyllithium is nonselective. 相似文献
6.
A. I. Verenich A. A. Govorova N. M. Galitskii V. I. Potkin R. V. Kaberdin Yu. A. Ol'dekop 《Chemistry of Heterocyclic Compounds》1992,28(3):336-339
X-ray structural data are used to demonstrate that the chlorine in the 5-position of the heterocycle is replaced on reaction of 3-trichloromethyl-4,5-dichloroisothiazole with sodium isopropoxide. The S-N and C-S bond lengths are lengthened in the resulting 3-trichloromethyl-4-chloro-5-isopropoxyisothiazole whereas the C-N and C-C bonds are shortened compared with analogous bonds in 4,5-dichloroisothiazole-3-carboxylic acid. This is explained by conjugation of the carboxylic acid with the heterocycle.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 399–402, March, 1992. 相似文献
7.
Butane-, phenylmethane-, and benzenethiols reacted with 4,5-dichloro-3-trichloromethyl-1,2-thiazole in the presence of sodium ethoxide to give the corresponding 5-alkyl(aryl)sulfanyl-4-chloro-3-trichloromethyl-1,2-thiazoles. The reaction of 4,5-dichloro-1,2-thiazole-3-carboxylic acid with the same thiols under similar conditions resulted in the formation of sodium 4,5-dichloro-1,2-thiazole-3-carboxylate, while in the presence of pyridine 5-alkyl(aryl)sulfanyl-4-chloro-1,2-thiazole-3-carboxylic acids were obtained. 相似文献
8.
V. I. Potkin V. A. Zapol''skii V. A. Knizhnikov R. V. Kaberdin A. A. Yanuchok S. K. Petkevich 《Russian Journal of Organic Chemistry》2001,37(5):689-694
Heating of 1-azolyl-1-(4-R-phenylamino)-2-nitro-3,4,4-trichloro-1,3-butadienes and 1-azolyl-1-(4-R-phenylamino)-2-nitro-3,4-dichloro-4-bromo-1,3-butadienes (R = BuO, EtO, MeO, Me; azolyl = 1-benzotriazolyl, 3,5-dimethyl-1-pyrazolyl, and 1,2,4-triazol-1-yl) in methanol or acetic acid gave the corresponding 2-(1-nitrotrihalopropenylidene)-4-R-benzazetines. The latter reacted with amines, sodium alkoxides, and sodium thiolates, affording salts of the aci-nitro form. The reactions with benzoyl chloride and chloroacetyl chloride in the presence of pyridine led to formation of mixed anhydrides. 相似文献
9.
V. I. Potkin S. K. Petkevich R. V. Kaberdin P. V. Kurman 《Russian Journal of Organic Chemistry》2007,43(11):1617-1621
Bromination of 3,4,4-trichlorobut-3-enoic acid in boiling carbon tetrachloride led to the formation of 2-bromo-3,4,4-trichlorobut-3-enoic acid as a result of replacement of hydrogen in the CH2 group. The reaction at 40°C involved the double C=C bond to give 3,4-dibromo-3,4,4-trichlorobutanoic acid. The brominated acids were converted into the corresponding chlorides which were used to acylate benzene, toluene, and bromobenzene according to Friedel-Crafts. The acylation was not selective, and only the reaction of 3,4-dibromo-3,4,4-trichlorobutanoyl chloride with benzene gave 3,4-dibromo-3,4,4-trichloro-1-phenylbutan-1-one as the only product. 1-Aryl-2-bromo-3,4,4-trichlorobut-3-en-1-ones were synthesized by bromination of the corresponding 1-aryl-3,4,4-trichlorobut-3-en-1-ones which were prepared previously by Friedel-Crafts acylation of substituted benzenes with 3,4,4-trichlorobut-3-enoyl chloride. 相似文献
10.
S. K. Petkevich V. I. Potkin R. V. Kaberdin 《Russian Journal of Organic Chemistry》2006,42(10):1481-1485
The reaction of 1-aryl-3,4,4-trichlorobut-3-en-1-ones with semicarbazide hydrochloride in the presence of sodium acetate is accompanied by prototropic allylic rearrangement, leading to the formation of two isomeric products, semicarbazones of the initial ketones and 1-aryl-3,4,4-trichlorobut-2-en-1-one semicarbazones. The latter undergo heterocyclization in the presence of triethylamine to give the corresponding 3-aryl-5-dichloromethyl-1H-pyrazole-1-carboxamides. 相似文献