Reaction products of 2-aminobenzenethiol with some β-diketones

2-Aminobenzenethiol undergoes condensation reactions with several β-diketones (CH₃, CF₃ and C₆H₅ substituents) to form benzothiazolines. Conversion to benzothiazines and benzothiazoles occurs in some instances, as documented by the isolation and spectroscopic characterization of the products.     

Reaction of 2-methylene-2,3-dihydroindoles with acrylamide

1,3-Dihydrospiro[2H-indolo-2,2-piperidine] derivatives were obtained by the reaction of 2-methylene-2,3-dihydro-1H-indole derivatives with acrylamide in proton-containing solvents. 2-(3-Carbamoylpropyl)-3H-indolium perchlorates were formed when the 1,3-dihydrospiro[2H-indolo-2,2-piperidine] derivatives were treated with perchloric acid.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 902–904, July, 1988.     

The reaction products of 2H-isoindole-4,7-dione derivatives with 2-aminobenzenethiol

From 2,3,4-Trisubstituted oxazolium-5-oxides and 2-methyl-, 2-phenyl- or 2-bromo-1,4-benzoquinone 1,2,3,5-tetrasubstituted 2H-isoindole-4,7-dione derivatives were prepared. These compounds were condensed with 2-aminobenzenethiol to produce 1,2,3-trisubstituted or 1,2,3,5-tetrasubstituted 4H-pyrrolo[3,4-a]phenothiazin-4-one derivatives. In the case of 1,2,3-trisubstituted 5-methyl-2H-isoindole-4,7-dione 1,2,3,5-tetrasubstituted 7-(2-mercaptophenyl)imino-2H-isoindole-4-one was obtained instead of the expected phenothiazinones.     

Reaction of 2,3-diaminomaleonitrile with diones

2,3-Diaminomaleonitrile (DAMN) was allowed to react with 2,6-heptanedione to produce (2Z)-2-amino-3-[(1E)-3-methylcyclohex-2-enylideneamino]but-2-enedinitrile and (2Z)-2-amino-3-[(1Z)-3-methylcyclohex-2-enylideneamino]but-2-enedinitrile. The reaction of DAMN with 2,7-octanedione yielded trans-5,8a-dimethyl-1,5a,6,7,8,8a-hexahydrocyclopenta[e]-1,4-diazepine-2,3-dicarbonitrile. DAMN reacted with 2,8-nonanedione to afford trans- and cis-5,9a-dimethyl-5a,6,7,8,9,9a-hexahydro-1H-benzo[e]-1,4-diazepine-2,3-dicarbonitrile. These compounds were characterized by X-ray crystallography, NMR spectroscopy, and DFT calculations.     

Reaction of aromatic o-diamines with isatins. 2. 2,3-diaminonaphthalene

The reaction of 2,3-diaminonaphthalene with isatins gives a mixture of indolo[2, 3-b]benzo[g]quinoxalines, 3-(2-aminophenyl)-2(1H)-benzo[g]quinoxalines, and spiro (2,3-d]imidazoline)-2,3-indolin-2ones. The ratio between the products is influenced by the solvent and the relative value of the positive charge on the -carbon atom in the isatin.For report 1 see [1].Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1399–1403, October, 1984.     

Reactions of fluoroalkyl-containing lithium 1,3-diketonates with diaminoarenes and 2-aminobenzenethiol

1,5-Benzo[b]- and 1,5-naphtho[2,3-b]diazepines were synthesized by the reaction of lithium 1,3-diketonates with 1,2-diaminobenzene and 2,3-diaminonaphthalene in an MeOH-AcOH-HCl mixture at 0 °C. The reactions of fluoroalkyl-containing lithium 1,3-diketonates with 1,2-diaminobenzene and 1,2-diamino-4,5-difluorobenzene under reflux in acetic acid afford 2-fluoroalkyl-containing benzimidazoles as the major products, whereas the reaction with 2-aminothiophenol gives 2-phenylbenzothiazole. The reactions of lithium diketonate containing the cyclohexane and cyclopentane moieties with 1,2-diaminoarenes and 2-aminobenzenethiol are accompanied by the opening of the carbocycle to form 2-(6-oxo-7,7,7-trifluoroheptyl)benzimidazole and 2-(5-oxo-6,6,6-trifluorohexyl)benzothiazole hydrates, respectively.     

Reaction of 2-(2-oxo-2,3-dihydro-1<Emphasis Type="Italic">H</Emphasis>-indol-3-ylidene)acetic acid esters with benzene-1,2-diamine and 2-aminobenzenethiol

2-(2-Oxo-2,3-dihydro-1H-indol-3-ylidene)acetic acid esters reacted with benzene-1,2-diamine or 2-aminobenzenethiol to give (2-oxo-2,3-dihydro-1H-indol-3-yl)-substituted 3,4-dihydroquinoxalin-2(1H)-ones or 2H-1,4-benzothiazin-3(4H)-ones.     

Reaction of 5-aryl-2,3-dihydrofuran-2,3-diones with ketene acetals

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, p. 1567, November, 1991.     

The Reaction of Molybdenum with 2,3-Dihydroxynaphthalene

[H2N（CH2）3NH312[MoO2（C10H6O2）2] （1） was synthesized by the 2,3-dihydroxynaphthalene in the mixed solvent of CH3OH, CH3CN reaction of （n-Bu4N）4[Mo8O26] with and 1,3-propanediarnine. （C5HllN2）2- [HeN（CH2）3NH2][MoO2（CloH6O2）2] （2） was obtained by the reaction of Na2MoO4.2H20 with 2,3-dihydroxynaphthalene in the same solvent above. Both of the complexes possess complex anion [Mo（VI）O2（OC10H6O）2]^2- which shows pseudo-octahedrally coordinated fashion, while the counterions are two protonated 1,3-propanediamine in complex 1 and （CsH11N2）^＋ in complex 2. （C5H11N2）＋ is the byproduct of reaction 2, which results from combination of acetonitrile with 1,3-propanediamine. Packing diagrams of the two complexes are also different. There is anti-parallel-aligned-double-meso-bilayer unit in complex 1. However there are four chiral anions arranged in anticlockwise orientation in complex 2.     

Five-membered 2,3-dioxo heterocycles. 21. Reaction of 1,5-diaryl-4-ethoxycarbonyl-tetrahydropyrrole-2,3-diones with 2-aminopyridine

The reaction of 2-aminopyridine with 1,5-diaryl-4-ethoxycarbonyltetrahydropyrrole-2,3-diones gave 11 complexes, which are converted to N-(2-pyridyl)-1,5-diaryl-3-hydroxy-2-oxo-2,5-dihydropyrrole-4-carboxamides when they are heated above their melting points without a solvent. The character of the hydrogen bonds in the complexes obtained is discussed.See [1] for Communication 20.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 32–36, January, 1992.     

Reaction of cytisine with alka-1,3- and -2,3-dien-2-ylphosphonates

Methods have been developed for functionalizing the alkaloid cytisine via introduction of alka-1,3- and -2,3-dien-2-ylphosphonate fragments. The main pathway of the reaction of cytisine with 2-(diethoxyphosphoryl) alka-2,3-dien-1-yl methanesulfonates is nucleophilic substitution of the methanesulfonyloxy group with retention of the alkadiene skeleton. A minor reaction pathway is nucleophilic substitution with formation of alka-1,3-dien-2-ylphosphonates. Cytisine conjugates with exclusively alka-1,3-dien-2-ylphosphonate fragment have been synthesized by copper(I)-catalyzed 1,3-dipolar cycloaddition of N-(prop-2-yn-1-yl)cytisine to 3-azidoalka-1,3-dien-2-ylphosphonates.     

Reaction of 2,3-dihydro-4-phenyl-1H-1,5-benzodiazepinethione-2 with acetylhydrazine

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, p. 1430, October, 1991.     

Reaction products of dialkyl acetylenedicarboxylates with 2,3-diaminopyridine

The condensation of dialkyl acetylenedicarboxylates 1 and 2 with 2,3-diaminopyridine (3) or its 5-bromo derivative 4 in ethanol gave pyrido[2,3-b]pyrazinones with a common side chain -CH₂-COOR at their 2-position, 5–7 , but in the presence of sulfuric acid the reaction afforded their isomers with the same side chain at the 3-position, 8–10 . All of the products were shown to exist in enamine form, in which a ring double bond has been displaced onto their side chain (?CH? COOR) being facilitated by an internal chelation as demonstrated by their ir and ₁H nmr spectra.     

Reaction of 2,3-Epoxypropyl Ethers with 1-Butanol

Nucleophilic opening of the oxirane ring in 2,3-epoxypropyl ethers with alcohols in the presence of titanium alkoxides and other catalysts was studied. The mechanism of catalysis by titanium alkoxides was discussed on the basis of comparison with acid–base catalysts.     

Reaction of 3-methyl-2,3-epoxysulfolane with alcohols

The corresponding dialkyl ethers of 3-methylsulfolane-2,3-diol are formed by the action of alcohols (methanol, ethanol, n-propyl alcohol, isopropyl alcohol, isobutyl alcohol, and n-octyl alcohol) on 3-methyl-2,3-epoxysulfolane in an acidic medium. The reaction proceeds through the intermediate formation of monoethers with subsequent etherification of the hydroxyl group by a second molecule of alcohol.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 613–615, May, 1979.     

Reaction of cis-2,3-dioctylaziridine with carboxylic acids

A series of aliphatic and aromatic carboxylic acids reacted with 2,3-dioctylaziridine to yield β-hydroxyalkyl amides in 69–89% yields and 2-substituted 4,5-di-n-octyl-δ²-oxazolines in amounts ranging from traces to 12% of the theoretical. No correlation could be found between carboxylic acid strength and either hydroxyamide or δ²-oxazoline yields. Solvents affected the product distribution.