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1.
A series of 3-chloro-5-halo(pseudohalo)-4H-1,2,6-thiadiazin-4-ones (halo/pseudohalo = Br, I, OTf) are prepared from 3,5-dichloro-4H-1,2,6-thiadiazin-4-one (3) in good yields. Of these the triflate reacts with tributyltin arenes (Stille couplings) chemoselectively to give only the 5-aryl-3-chloro-4H-1,2,6-thiadiazin-4-ones in high yields. This allowed the preparation of a series of unsymmetrical biaryl thiadiazines and ultimately a series of oligomers. Furthermore, treatment of 3-chloro-5-iodo-4H-1,2,6-thiadiazin-4-one (10) with Bu(3)SnH and Pd(OAc)(2) gave the bithiadiazinone which can also be further arylated via the Stille reaction to give bisthien-2-yl and bis(N-methylpyrrol-2-yl) analogs. 相似文献
2.
The synthesis of 2-(1H-imidazol-1-yl)-4H-1-benzothiopyran- 4 -ones 3 from 3-bromo-4H-1-benzothiopyran-4-ones 1 and imidazole is described. The reaction of 1 with secondary amines gives the corresponding 3 -amino-thiochromones 11. Compounds 3 can be oxidized to the sulfones 4 from which the thiochromanols 5 and thiochromene 7 can be easily obtained. 3-Bromo-2,3-dihydro-6-methyl-4H-1-benzothiopyran-4-one 12 and imidazole led by dehydrohalogenation to thiochromone, while the ketal 13 rearranged to benzo[b]thiophene 16. 相似文献
3.
J
Rg Bader 《Helvetica chimica acta》1968,51(6):1421-1438
Asymmetrically substituted 5-sulfonyl-1, 3-dithiafulvenes (9a–g), all of which have the same configuration (called α), are obtained by reaction of 4-chloro-5-sulfonyl-1, 2-dithiol-3-ones (3a–e) with sodium alkoxides. Side-products formed are 4-chloro-5-alkoxy-1, 2-dithiol-3-ones (5a and 5b), 3, 5-bis-alkylidene-1, 2, 4-trithiacyclopentanes (21 and 22), and (in some instances) minor amounts of compounds 33, 34, or 35. Reaction of 4-phenyl-5-methylsulfonyl-1, 2-dithiol-3-one with sodium methoxide results in the formation of 4-phenyl-5-methoxy-1, 2-dithiol-3-one (5c), the two cis-trans-isomers of 2, 4-bis-alkylidene-1, 3-dithiacyclobutane 24 and 25, and the 2, 5-bis-alkylidene-1, 2, 4, 5-tetrathiacyclohexane 26. Some conceivable reaction mechanisms are discussed, and proof is given for the structure of the major compounds. By treating 4-chloro-5-(2′-chloro-ethylthio)-1, 2-dithiol-3-one with sodium methoxide, the 2-alkylidene-1, 3-dithiolane 13 is obtained. The sulfonyl groups of the 1, 3-dithiafulvenes 9a–g described may be easily replaced by hydrogen or secondary amines, yielding compounds 14, 16 and 19, respectively. When dissolved in strong acids and reprecipitated, asymmetrically substituted 2-alkylidene-1, 3-dithia compounds may be converted into mixtures of all possible cis-trans-isomers thereof. Those isomers may be separated by fractional crystallization. Isomers 31 (called β) of 9 a--g, and 32 of 16a, b, are obtained accordingly. 相似文献
4.
Sixteen new 1-[5-chloro-1-substituted-2(1H)-pyrazin-2-on-3-yl]-5-aryl-3-methylpyrazoles V have been synthesized by condensation of 5-chloro-1-substituted-3-hydrazino-2(1H)-pyrazin-2-ones III and 1-aryl-1,3-butanediones IV in dry 1,4-dioxane. The general mass spectral fragmentation mode of these compounds has been studied. 相似文献
5.
A reaction of 3-allyl- and 3-phenylthiohydantoins with 1,5-diphenyl- and 1-phenyl-substituted 3-formyl-2-pyrazolines was used to obtain a series of 5-(pyrazolin-3-ylmethylidene)-2-thioxotetrahydro-4H-imidazol-4-ones, the subsequent alkylation of which with methyl iodide or ethyl chloroacetate gave the corresponding 2-alkylthio-5-(pyrazolin-3-ylmethylidene)-3,5-dihydro-4H-imidazol-4-ones in the yields from 30 to 77%. The oxidation of (5Z)-3-phenyl-5-[(1,5-diphenylpyrazolin-3-yl)methylidene]-2-methylsulfanyl-4,5-dihydroimidazol-4-one with lead tetraacetate led to the corresponding pyrazole in 48% yield. 相似文献
6.
James H. Looker Duane L. Shaneyfelt Wayne Halfar 《Journal of heterocyclic chemistry》1979,16(6):1281-1282
Condensation reactions of comenaldehyde methyl ether (I) with malonic acid, ethyl cyanoacetate, and cyanoacetamide to give β-(5-methoxy-4H-pyran-4-on-2-yl)acrylic acid (II), ethyl 2-cyano-3-(5-methoxy-4H-pyran-4-on-2-yl)propenoate (III), and 2-cyano-3-(5-methoxy-4H-pyran-4-on-2-yl)propenamide (IV), respectively, are described. Ultraviolet absorption spectra for 2-hydroxymethyl-5-methoxy-4H-pyran-4-one, I and II are presented. 相似文献
7.
Reaction of 1-(3-bromo-2-oxopropyl)pyridazin-6-ones 1 and 2 with sodium azide at room temperature gave the corresponding 1-(3-azido-2-oxopropyl)pyridazin-6-ones 3 and 4 , whereas reaction of 1-(1-bromo-2-oxo-propyl)pyridazin-6-ones 5 and 6 with excess sodium azide afforded 4-azido-5-chloropyridazin-6-one 7 and 4,5-diazido-3-nitropyridazin-6-one 8 by dealkylation. Some 1-(2-hydroxypropyl)pyridazin-6-ones 9, 10, 11 were synthesized from the corresponding 1-(2-oxopropyl) derivatives 1, 2, 3 . 4,5-Dichloro-1-(2,3-dihydroxypropyl)-pyridazin-6-one 13 was also prepared from compound 9 via the corresponding 2,3-epoxypropyl derivative 12 . Treatment of compound 5 with thiourea gave 4,5-dichloro-1-(2-amino-4-methylthiazol-5-yl)pyridazin-6-one 14 . Reaction of compounds 1 and 2 with thiourea at 20° afforded the corresponding 3-formamidinylthio-2-oxo-propyl derivatives 15 and 16 , whereas treatment of compound 1 with thiourea at 45° gave 4,5-dichloro-1-[(2-aminothiazol-5-yl)methyl]pyridazin-6-one 17 . Compound 17 was also prepared from compound 15 by refluxing in ethanol. 相似文献
8.
L. N. Sobenina Z. V. Stepanova O. V. Petrova J. Sh. Ma G. Yang A. A. Tatarinova A. I. Mikhaleva B. A. Trofimov 《Russian Chemical Bulletin》2013,62(1):88-92
Cross-coupling of 2-(biphenyl-4-yl)pyrroles derived from 1-(biphenyl-4-yl)ethanone oximes and acetylene with 3-bromo-1-phenylprop-2-yn-1-one on aluminum oxide gave 3-[5-(biphe-nyl-4-yl)pyrrol-2-yl]-1-phenylprop-2-yn-1-ones in 35–46% yields. 相似文献
9.
F. A. Gimalova E. M. Minnibaeva M. S. Miftakhov 《Russian Journal of Organic Chemistry》2007,43(11):1651-1655
2,3,5-Trichloro-4,4-dimethoxy-5-(2-methylfuran-3-yl)cyclopent-2-en-1-one reacted with secondary amines to give unusual AdNE-substitution-fragmentation products, 5-[(1Z,2E)-1-acetyl-3-dialkylaminoprop-2-en-1-ylidene]-3-dialkylamino-2-chloro-4,4-dimethoxycyclopent-2-en-1-ones. 相似文献
10.
I. Yu. Danilyuk R. I. Vas’kevich A. I. Vas’kevich M. V. Vovk 《Russian Journal of Organic Chemistry》2016,52(7):987-992
Intramolecular cyclization of 4-aryl-N-(thiophen-3-yl)but-3-enamides on heating in polyphosphoric acid afforded 8-aryl-4,6,7,8-tetrahydro-5H-thieno[3,2-b]azepin-5-ones and 5-aryl-1-(thiophen-3-yl)pyrrolidin-2-ones. Cyclofunctionalization of the title compounds with (chlorosulfanyl)benzene and 4-(chlorosulfanyl)-toluene led to the formation of 8-aryl-7-arylsulfanyl-4,6,7,8-tetrahydro-5H-thieno[3,2-b]azepin-5-ones or their mixtures with 5-aryl-4-arylsulfanyltetrahydrofuran-2-ones. 1-(Chlorosulfanyl)-4-nitrobenzene reacted with 4-(4-methylphenyl)-N-(thiophen-3-yl)but-3-enamide and 4-(4-fluorophenyl)-N-(thiophen-3-yl)but-3-enamide to give 5-(4-methylphenyl)-4-(4-nitrophenylsulfanyl)-1-(thiophen-3-yl)pyrrolidin-2-one and 5-(4-fluorophenyl)-4-(4-nitrophenylsulfanyl)tetrahydrofuran-2-one, respectively. 相似文献
11.
Nguyen P Corpuz E Heidelbaugh TM Chow K Garst ME 《The Journal of organic chemistry》2003,68(26):10195-10198
A regioselective oxidation of N-indan-4-yl-acetamide or N-(5,6,7,8-tetrahydronaphthalen-1-yl)acetamide with potassium permanganate followed by acidic hydrolysis gave 7-aminoindan-1-one or 8-aminotetral-1-one in good yield. The amino ketones were converted to the corresponding 7-haloindanone or the 8-halotetralone. Another method to prepare 7-haloindan-1-ones was completed by a cyclization of 3-chloro-1-(2-halophenyl)propan-1-one under Friedel-Crafts conditions to produce the product in gram quantity. 相似文献
12.
The preparation of 1,4-dihydro-4-oxo-3′-alkylthio-3,4′-diquinolinyl sulfides 3 or 1,4-dihydro-4-oxo-3-(alkylthio)quinolines 4 by acid catalysed hydrolysis of 4-methoxy-3′-alkylthio-3,4′-diquinolinyl sulfides 1 or 4-methoxy-3-(alkylthio)-quinolines 2 is described. The reactions of 4-methoxy-3′-alkylthio-3,4′-diquinolinyl sulfides 1 or 1,4-dihydro-4-oxo-3′-alkylthio-3,4′-diquinolinyl sulfides 3 with phosphoryl chloride in DMF afforded 4-chloro-3′-alkylthio-3,4′-diquinolinyl sulfides 5 . Treatment of the title compounds 1 or 3 with boiling phosphoryl chloride systems:leads to 4-chloro-3-(alkylthio)quinolines 6 and thioquinanthrene but those of alkoxy- or oxo-quinolines 2 or 4 lead to 4-chloro-3-(alkylthio)quinolines 6 . The reactions of N-methyl-4(1H)-quinolinones 3n and 4n with phosphoryl chloride directed to 4-chloro-3-(alkylthio)quinolines 6 were studied as well. 相似文献
13.
Yu. A. Sayapin E. A. Gusakov Zyong Ngia Bang I. O. Tupaeva V. N. Komissarov I. V. Dorogan V. V. Tkachev S. M. Aldoshin V. I. Minkin 《Russian Chemical Bulletin》2013,62(2):480-491
A reaction of substituted 2-(quinolin-2-yl)-1,3-tropolones with POCl3 leads to the new3-chloro-2-(quinolin-2-yl)tropone derivatives. New 2-(4-arylaminoquinolin-2-yl)-3-aryl-aminocyclohepta-2,4,6-trien-1-ones and 2-[4-morpholino(piperidino)quinolin-2-yl]-3-aryl-aminocyclohepta-2,4,6-trien-1-ones were obtained by nucleophilic substitution reaction of the halogen atom in 2-(4-chloroquinolin-2-yl)-3-chlorotropones and 3-chloro-2-[4-morpholino-(piperidino)quinolin-2-yl]tropones. Molecular structures of 3-chloro-2-(quinolin-2-yl)tropone and 3-arylamino-2-(quinolin-2-yl)tropone were established by X-ray diffraction analysis. Energy and structural characteristics of isomers of 3-arylamino-2-(quinolin-2-yl)tropones in the gas phase and in solution were calculated by the density functional theory method (PBE0/6-31G**). 相似文献
14.
Johannes Reisch Andreas Bathe Bernd H. W. Rosenthal Reza A. Salehi-Artimani 《Journal of heterocyclic chemistry》1987,24(3):869-872
Pyrano[3,2-c]quinoline alkaloids 3 , suitable precursor for photobiomimetic dimerisations, are available by ptc-reactions of 4-hydroxyquinoline-2-ones 1 with 3-chloro-3-methylbut-1-yne, as byproducts uro[3,2-c]-quinoline-2-one is isomeres 5 are found. In the synthesis of flindersine ( 3a ) additionally the oxazolo[3,2-a]quinolin-5-one 4 could be isolated, while in the preparation of N-methylflindersine ( 3b ) a bis-(N-methyal-4′-hydroxyquinolin-2′-one-3′-yl)isopentene ( 7 ) was identified. Alkaloid dimers, which may be formed from the intermediates 6 , were not present. The structure of 7 confirms reaction pathways, discussed previously. Haplophylline ( 3c ) is synthesized for the first time by N-alkylation a of 3a with 3-methylcrotonyal chlormethyl ester. 相似文献
15.
E.G. Frandsen 《Tetrahedron》1977,33(8):869-873
The reaction of 4- and 5-aryl-3-methylthio-1,2-dithiolylium iodides with 4-hydroxy-6-methyl-2-pyran-2-one and 4-hydroxycoumarin has been studied. 4-Substituted salts yielded 3-aryl-7-methyl-2-thioxo-2,5-pyrano [3,2-c]pyran-5-ones and 3-aryl-2-thioxo-2H,5H-pyrano[3,2-c]benzo[e]pyran-5-ones, respectively, whereas 5-substituted salts gave rise to 3-(5′-aryl-1′,2′-dithiol-3′-ylidene)-6-methyl-2-pyran-2,4-diones and 3-(5′-aryl-1′,2′-dithiol-3′-ylidene)-2-benzo [b]-pyran-2,4-diones. 相似文献
16.
M. A. El-Badawi A. A. El-Barbary Y. M. Lokshaa Mai El-Daly 《Phosphorus, sulfur, and silicon and the related elements》2013,188(3):587-596
Some of novel N , N '-bis-(1,2,4-triazin-4-yl)dicarboxylic acid amides ( 2-5 ) and thiadiazolo[2,3- b ][1,2,4]triazin-7-yl carboxylic acid derivatives ( 6 , 7 ) were prepared by heating 4-amino-6-methyl-5-oxo-3-thioxo-2,3,4,5-tetrahydro-1,2,4-triazine ( 1 ) with different dicarboxylic acids (oxalic, malonic, fumaric, maleic, succinic, and phthalic acids respectively) in POCl 3 . Refluxing 1 with 1-chloro-2,4-dinitrobenzene in DMF yielded 3-methyl-6-nitro-10 H -benzo[1,2,4]thiadiazino[2,3- c ][1,2,4]triazin-4-one ( 8 ). Condensation of 1 with 2,4-pentandione in refluxing acetic acid furnished 6-methyl-4-(1-methyl-3-oxobut-1-enylamino)-3-thioxo-3,4-dihydro-2 H -[1,2,4]triazin-5-one ( 9 ). 3,8-D imethyl[1,2,4] triazino[3,4- b ][1,3,4]thiadiazine-4,7-dione ( 11 ) was prepared by refluxing 1 with 2-bromopropionyl bromide in anhydrous benzene to afford the corresponding N -acetylated derivative 10 , which was cyclized by using triethylamine. Also, some triazinylquinazolinones 13a , b were obtained by fusion of 1 with 6-bromo(and/or 6,8-dibromo)-2-methyl-3,1-benzoxazin-4 H -ones. 相似文献
17.
E. A. Borodina N. A. Orlova Yu. V. Gatilov O. I. Sal’nikova 《Russian Journal of Organic Chemistry》2015,51(12):1745-1752
Reactions of polyfluorinated chalcones with guanidine in the presence of bases are accompanied by elimination of the polyfluorophenyl group. 3-(Pentafluorophenyl)-1-phenylprop-2-en-1-one and its derivatives reacted with guanidine under basic conditions to give 4-phenylpyrimidin-2-amine, polyfluorobenzenes, and Michael adducts, 3-(2-amino-4-phenylpyrimidin-5-yl)-3-(4-R-2,3,5,6-tetrafluorophenyl)-1-phenylpropan-1-ones. 1-(Pentafluorophenyl)-3-phenylprop-2-en-1-one and 1,3-bis(pentafluorophenyl)prop-2-en-1-one were converted into cinnamic acid derivatives whose reaction with guanidine afforded 2-amino-6-aryl-5,6-dihydropyrimidin-4(1H)-ones. 相似文献
18.
The synthesis of 2-chloro-1-(β-D -ribofuranosyl)-5,6-dimethylbenzimidazole (3b) has been accomplished by a condensation of 1-trimethylsilyl-2-chloro-5,6-dimethylbenzimidazole (1) with 2,3,5-tri-O-acetyl-D -ribofuranosyl bromide (2) followed by subsequent deacetylation. Nucleophilic displacement of the 2-chloro group from 3b has furnished several interesting 2-substituted-1-(β-D -ribofuranosyl)-5,6-dimethylbenzimidazoles. 1-(β-D -Ribofuranosyl)-5,6-dimethylbenzimidazole (5) and 1-(β-D -ribofuranosyl)-5,6-dimethylbenzimidazole-2-thione (4) were prepared from 3b. Alkylation of 4 furnished certain 2-alkylthio-1-(β-D -ribofuranosyl)-5,6-dirnethylbenzimidazoles and oxidation of 4 with alkaline hydrogen peroxide produced 1-(β-D -ribofuranosyl)-5,6-dimethylbenzimidazole-2-one D The assignment of anomeric configuration for all nucleosides reported is discussed. 相似文献
19.
R. Ian Fryer D. L. Coffen J. V. Earley A. Walser 《Journal of heterocyclic chemistry》1973,10(4):473-478
The preparation of the title compounds 3 and 4 using two different methods of synthesis is described. These compounds are readily reduced to 2,3-dihydro-1H-derivatives 5 . Oxidation of 2-alkylthio-1H-1,4-benzodiazepines leads to the corresponding sulfoxides and sulfones. The oxidative rearrangement of sulfones 9 to a 2H-1,4-benzodiazepin-2-one derivative 10 is also given. The “normal” addition of azodicarboxylate together with an unusual addition of two moles of acetylenedicarboxylate to the enamine double bond of 1H compounds is discussed. 相似文献
20.
Alex F. C. Flores Juliana L. Malavolta Leandro M. Frigo Morgana Doneda Darlene C. Flores 《合成通讯》2013,43(10):1198-1204
We develop an efficient method to synthesize novel propionyl-spaced bisheterocyclic compounds. It entails cyclocondensation of 3-(5-trifluoromethyl-1H-pyrazol-3-yl)propanoyl hydrazide obtained from levulinic acid, with 1,1,1-trifluoro-4-methoxy-3-alken-2-ones proceeding regiospecifically to 1-[(5-trifluoromethyl-5-hydroxy-3-substituted-4,5-dihydro-1H-pyrazol-1-yl)-3-(5-trifluoromethyl-1H-pyrazol-3-yl)propan-1-one derivatives. 相似文献