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1.
The nature of the compounds afforded by the rearrangement of the aminopropylation and aminoethylation products of tetrahydro-2H-1,3-oxazine-2-thione (I) has been investigated. In both instances compounds that can be considered to result from ring opening at either the C-O or C-S bond of a hypothetical bicyclic intermediate of structure IV were obtained. The compounds required for identification of the rearrangement products have been prepared by the reaction of the 2-methylthio derivatives of 2-thiazoline, 5,6-dihydro-4H-1,3-thiazine, and 5,6-dihydro-4H-1,3-oxazine with the appropriate hydroxyalkylamine or mercaptoalkylamine. 相似文献
2.
An original montmorillonite K-10 clay catalysed cycloisomerisation of salicylaldehyde 4-arylthiosemicarbazones yields 3,4-dihydro-4-hydrazino-2H-benz[e]-1,3-oxazine-2-thiones, which on reductive dehydrazination on alumina-supported copper(II) sulfate readily furnish 3,4-dihydro-2H-benz[e]-1,3-oxazine-2-thiones under solvent-free microwave irradiation. Under the same conditions salicylaldehyde thiosemicarbazones undergo cyclodehydrazination to yield 2H-benz[e]-1,3-oxazine-2-thiones. 相似文献
3.
Francesca Benedini Giorgio Bertolini Francesco Ferrario Angelo Motti Alberto Sala Flavio Somenzi 《Journal of heterocyclic chemistry》1995,32(1):103-107
The preparation and the physico-chemical characterization of 2H-pyrido[2,3-e]-1,3-oxazine-2,4(3H)-diones, 2H-pyrido[4,3-e]-1,3-oxazine-2,4(3H)-diones, 2H-pyrido[4,3-e]-1,3-oxazin-4(3H)-ones, 2H-thieno[2,3-e]-1,3-oxazin-4(3H)-ones and 2H-thieno[3,4-e]-1,3-oxazine-2,4(3H)-diones are reported. 相似文献
4.
Treatment of 4-fluoro-5-(1,1,2,2-tetrafluoroethyl)-3H-1,2-dithiole-3-thione with 2 equivalents of sodium sulfide gives after acidification 3,4-difluoro-2-mercapto-1,6,6aλ4-trithiapentalene, which can be further reduced by sodium sulfide to 3,5-difluoro-4-mercapto-thiopyran-2-thione. 相似文献
5.
Reaction of 3-(Dimethylamino)-2H-azirines with 1,3-Oxazolidine-2-thione to 3-(2-Hydroxyethyl)-2- thiohydantoins The reaction of 3-(dimethylamino)-2H-azirines 1 and 1,3-oxazolidine-2-thione ( 6 ), in MeCN at room temperature, yields, after hydrolytic workup, 3-(2-hydroxyethyl)-2-thiohydantoins 7 (Scheme 2). In the case of the spirocyclic 1c , crystallization of the crude reaction mixture leads to spiro [cyclopentane-1, 7′(7′aH)-imidazo [4, 3-b] oxazole] -5′-thione 8c . The mechanism is discussed. 相似文献
6.
E. A. Ignatenko E. V. Shklyaeva G. G. Abashev 《Russian Journal of Organic Chemistry》2013,49(9):1379-1385
The reaction of 1-(3-bromopropyl)-2,5-bis(thiophen-2-yl)-1H-pyrrole with cesium 5-methylsulfanyl-2-thioxo-1,3-dithiole-4-thiolate generated in situ gave previously unknown 4-{3-[2,5-bis(thiophen-2-yl)-1H-pyrrol-1-yl]propylsulfanyl}-5-methylsulfanyl-1,3-dithiole-2-thione, and cross-coupling of the latter with 4,5-disubstituted 1,3-dithiole-2-thiones in the presence of triethyl phosphite afforded new substituted tetrathiafulvalenes containing a 2,5-bis(thiophen-2-yl)pyrrole fragment. Optical properties and electrochemical behavior of the synthesized compounds were studied, and their ability to undergo electropolymerization was confirmed. 相似文献
7.
V. N. Britsun A. N. Borisevich A. N. Esipenko M. O. Lozinskii 《Russian Journal of Organic Chemistry》2007,43(1):103-107
N-Aryl-3-oxobutanethioamides react with 2-amino-1,3-thiazole (2-amino-1,3-benzothiazole) in acetic acid to give mixtures of 7-methyl-5H-[1,3]thiazolo[3,2-a]pyrimidine-5-thione (2-methyl-4H-pyrimido-[2,1-b][1,3]benzothiazole-4-thione) and 5-arylimino-7-methyl-5H-[1,3]thiazolo[3,2-a]pyrimidines (4-arylimino-2-methyl-4H-pyrimido[2,1-b][1,3]benzothiazoles), whose ratio depends on the nature of the aryl substituent in the initial butanethioamide. 相似文献
8.
A. A. Rzhevskii N. P. Gerasimova E. M. Alov O. S. Kozlova A. S. Danilova S. A. Khapova K. Yu. Suponitskii 《Russian Chemical Bulletin》2012,61(11):2133-2136
Reactions of triazolethiones with haloacetic acids were studied with 5-(4-methylphenyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione as an example. It was proved for the first time by X-ray diffraction that the cyclocondensation of these compounds proceeds regiospecifically to give 2-(4-methylphenyl)[1,3]thiazolo[3,2-b][1,2,4]triazol-6(5H)-one rather than its isomer 3-(4-methylphenyl)[1,3]thiazolo[2,3-c][1,2,4]triazol-5(6H)-one. 相似文献
9.
A. V. Peretokin A. S. Moskovkin I. V. Miroshnichenko M. Ya. Botnikov Yu. F. Malina B. V. Unkovskii 《Chemistry of Heterocyclic Compounds》1989,25(12):1390-1393
The syntheses and mass spectra of 5,6-tetramethylenetetrahydro-1,3-oxazine-2-thione and its 4-mono- and 4,4-disubstituted analogs are reported. The primary decay processes under electron impact are loss of the 1,3-oxazine ring, formation of hydrocarbon ions, and rearrangement of the [M–C6H9]+ ion.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1668–1672, December, 1989. 相似文献
10.
Dimethyl 3-(aryl)-3,6-dihydro-2H-1,3-oxazine-4,5-dicarboxylate structure assigned for the products obtained in the Bronsted acid catalyzed reaction of dimethyl but-2-ynoates with anilines and an excess of formaldehyde in methanol has been revised to methyl 1-(aryl)-3-(methoxymethyl)-4,5-dioxopyrrolidine-3-carboxylate. 相似文献
11.
N. I. Korotkikh G. F. Raenko T. M. Pekhtereva O. P. Shvaika A. H. Cowley J. N. Jones 《Russian Journal of Organic Chemistry》2006,42(12):1822-1833
A new stable crystalline carbene, 1,3-bis(1-adamantyl)benzimidazol-2-ylidene, was synthesized by decomposition of 1,3-bis(1-adamantyl)-2,3-dihydro-1H-benzimidazol-2-ylacetonitrile on heating under reduced pressure. Heteroaromatic 1,3-R2-disubstituted benzimidazol-2-ylidenes, both stable (R = 1-Ad) and generated in situ (R = Me, Bzl), as well as 1,3,4,5-tetraphenylimidazol-2-ylidene (generated in situ), reacted with acetonitrile to give the corresponding insertion products, 1,3-disubstituted 2-cyanomethyl-2,3-dihidro-1H-(benz)-imidazoles. The geometric parameters of 1,3-bis(1-adamantyl)benzimidazol-2-ylidene, determined by X-ray analysis, suggest its lower aromaticity as compared to imidazol-2-ylidenes and 1,2,4-triazol-5-ylidenes. The structures of 2-cyanomethyl-2,3-dihydro-1H-benzimidazoles, 2-cyanomethyl-1,3,4,5-tetraphenyl-2,3-dihydro-1H-imidazole, and 1-(1-adamantyl)-5-cyanomethyl-3,4-diphenyl-4,5-dihydro-1H-1,2,4-triazole are characterized by partial conjugation in the heteroring; some compounds exhibit luminescence under UV irradiation. 1,3-Bis(1-adamantyl)benzimidazol-2-ylidene reacted with molecular sulfur in benzene to give 1,3-bis-(1-adamantyl)-2,3-dihydro-1H-benzimidazole-2-thione, but it failed to react with selenium under analogous conditions. 相似文献
12.
1-Chlorobenzyl isocyanates react with 4-hydroxy-6-methylpyran-2-one and 4-hydroxycoumarin forming 4-aryl-3,4-dihydro-2H,5H-pyrano(chromeno)[3,4-e][1,3]oxazine-2,5-diones. The reaction of 1-aryl-2,2,2-trifluoro-1-chloroethyl isocyanates with the above substrates gives rise to structurally isomeric 2-aryl-2-trifluoromethyl-2,3-dihydro-2H,5H-pyrano(chromeno)[3,4-e][1,3]-oxazine-4,5-diones. 相似文献
13.
Nobuhiro Kihara Hidefumi Tochigi Takeshi Endo 《Journal of polymer science. Part A, Polymer chemistry》1995,33(7):1005-1010
5-(Methacryloyloxy)methyl-1,3-oxathiolane-2-thione ( 3 ) was synthesized from glycidyl methacrylate (GMA) and carbon disulfide in the presence of lithium bromide in 93% yield. The radical polymerization of 3 in DMSO initiated by AIBN at 60°C afforded corresponding polymethacrylate 4 quantitatively. Copolymerization of 3 with MMA was also carried out. 5-Phenoxymethyl-1,3-oxathiolane-2-thione ( 6 ), model dithiocarbonate, reacts with benzylamine at room temperature to afford O-(1-mercapto-3-phenoxy-2-propyl)N-benzyl-thiocarbamate ( 7 ) and 1,1′-dithiobis[3-phenoxy-2-(benzylaminothiocarbonyloxy)-propane] ( 8 ) in 89% and 7% yield, respectively. Polymer 4 reacted with butylamine or dipropylamine to afford a corresponding polymethacrylate bearing thiol group, which immediately turned to insoluble gel by facile auto-oxidation of the thiol group. © 1995 John Wiley & Sons, Inc. 相似文献
14.
4-Hydroxy-2H-chromen-2-one and 4-hydroxy-2H-chromene-2-thione reacted with allyl bromide, 1,1,3-trichloroprop-1-ene, and 1,3-dichlorobut-2-ene to give the corresponding ethers, which were oxidized to (2-oxo-2H-chromen-4-yloxy)acetic acid with potassium permanganate, and various derivatives of that acid were obtained. 3-(3,3-Dichloroprop-2-enyl)-7-hydroxy-4-methyl-2H-chromen-2-one and 3-(3,3-dichloroprop-2-enyl)-7-hydroxy-4-methyl-2H-chromene-2-thione were synthesized, and some their transformations were studied. 相似文献
15.
Masataka Yokoyama Hiroshi Inazawa Tomoji Shimizu Masahito Kodera Tsuneo Imamoto 《Phosphorus, sulfur, and silicon and the related elements》2013,188(1-2):187-193
Abstract Two 1,3-oxazine-6-thione derivatives obtained by “S,N-Double Rearrangement2” reacted with several nucleophiles to produce 1,3-diazin-6-ones, 6-imino-1,3-oxazines, 1,3,4-triazoles, 1,2,4-oxadiazoles, and 1,3-thiazol-6-ones. Their ring transformations are discussed. 相似文献
16.
1H,3H-Imidazo[1,5-c]thiazole-5,7-[6H,7aH]-dione and the corresponding 7-thione derivatives as well as 7,8-dihydro-5H-imidazo[1,5-c][1,3]thiazine-1,3-[2H,8aH]-dione and the corresponding 3-thione derivatives were synthesized starting from L -cysteine and DL -homocysteine thiolactone, respectively. The second group of bicyclic compounds represents a new heterocyclic ring system. The structures of the compounds were confirmed by spectroscopic studies and elemental analyses. 相似文献
17.
L. G. Shagun I. A. Dorofeev I. A. Mikhailova V. A. Shagun M. G. Voronkov 《Chemistry of Heterocyclic Compounds》2006,42(11):1478-1481
The reaction of 8-mercaptoquinolinium bromide with 1,3-dibromopropane-2-thione or 3,3-dibromobutane-2-thione in methanol gave
the 2-bromomethyl-2-mercaptotetrahydro-1,4-thiazino[2,3,3,4-i,j]quinolinium and 3-bromo-2-mercapto-2,3-dimethyltetrahydro-1,4-thiazino[2,3,3,4-i,j]quinolinium
bromides which readily exchanged the Br− anion for ClO
4
−
upon treatment with sodium perchlorate in methanol. Oxidation of the 3-bromo-2-mercapto-2,3-dimethyltetrahydro-1,4-thiazino[2,3,3,4-i,j]-quinolinium
bromide by selenium dioxide gave 2,2-dithiobis(3-bromo-2,3-dimethyltetrahydro-1,4-thiazino[2,3,3,4-i,j]quinolinium) bromide.
__________
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1720–1723, November, 2006. 相似文献
18.
The domino [2+2+2] cycloaddition reaction of α,β-unsaturated N-arylaldimines, dialkyl acetylenedicarboxylates and 2-arylidene-1,3-indanediones in dry methylene dichloride at room temperature afforded isomeric 2′-styryl-1,2′,3,4′-tetrahydro-1′H-spiro[indene-2,3′-pyridines] in good yields. Under similar conditions, the reaction of α,β-unsaturated N-arylaldimines with two molecules of dialkyl acetylenedicarboxylates resulted in 1-aryl-6-styryl-1,6-dihydropyridine-2,3,4,5-tetracarboxylates. Additionally, the three-component reaction of α,β-unsaturated N-arylaldimines, dimethylacetylenedicarboxylate and benzoyl cyanide also gave isomeric 1,3-oxazine-4,5-dicarboxylates. 相似文献
19.
Reaction of 3-(Dimethylamino)-2H-azirines with 1,3-Benzoxazole-2(3H)-thione The reaction of 3-(dimethylamino)-2H-azirines 2 with 1,3-benzoxazole-2(3H)-thione ( 5 ), which can be considered as NH-acidic heterocycle (pKaca. 7.3), in MeCN at room temperature, leads to 3-(2-hydroxyphenyl)-2-thiohydantoins 6 and thiourea derivatives of type 7 (Scheme 2). A reaction mechanism for the formation of the products via the crucial zwitterionic intermediate A ′ is suggested. This intermediate was trapped by methylation with Mel and hydrolysis to give 9 (Scheme 4). Under normal reaction conditions, A ′ undergoes a ring opening to B which is hydrolyzed during workup to yield 6 or rearranges to give the thiourea 7. A reasonable intermediate of the latter transformation is the isothiocyanate E (Scheme 3) which also could be trapped by morpholine. In i-PrOH at 55–65° 2a and 5 react to yield a mixture of 6a , 2-(isopropylthio)-1,3-benzoxazole ( 12 ), and the thioamide 13 (Scheme 5). A mechanism for the surprising alkylation of 5 via the intermediate 2-amino-2-alkoxyaziridine F is proposed. Again via an aziridine, e.g. H ( Scheme 6 ), the formation of 13 can be explained. 相似文献
20.
K. Schweiger A. Fuchsgruber Prof. Dr. G. Zigeuner 《Monatshefte für Chemie / Chemical Monthly》1977,108(1):257-263
Tetrahydro-6-hydroxy-4,4,6-trimethyl-1,3-thiazine-2-thione (1 a) reacts with methyl-, ethyl- and n-butylamine to the corresponding 1-alkyl-6-alkylaminotetrahydro-2(1H)-pyrimidinethione12 but withi-propylamine to tetrahydro-6-isopropylamino-1,3-thiazine-2-thione (6 d). On treatment withDCC,6 d is rearranged to dihydro-4-isopropylamino-2(1H)-pyridinethione (8 d), and 6-amino-tetrahydro-1,3-thiazinethione (6 a) to dihydro-4,4,6-trimethyl-2(1H)-pyrimidinethione (10 a). The reaction of 6-aminothiazinethiones6 a, d and 6-(4-morpholinyl)-thiazinethione13 resp., with methylamine leads to 1-methyl-6-methylamino-pyridinethione12 b. 1-Alkyl-6-alkylamino-tetrahydro-2(1H)-pyrimidinethiones (12) react at reflux temperature to dihydro-1-alkylpyrimidinethiones10. With methylamine only 6-methylamino-3,4,4,6-tetramethyl-1,3-thiazine-2-thione (6 f) is formed from tetrahydro-6-hydroxy-tetramethyl-1,3-thiazine-2-thione (1 b). 相似文献