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1.
Phthalazinone and pyridopyridazinone derivatives 3, 5, and 9 were prepared via reaction ofappropriate lactams 2 and 8 with 2-bromoethylphthalimide, N-tosylaziridine, and N,O-ditosyl derivatives of N-methylethanolamine in a two-step process in the presence of MeONa/MeOH or NaH/dimethylformamide (DMF). Starting compounds 2 and 8 were obtained by reaction of hydrazine hydrate with isoindolinones 1 or azaisoindolinones 6. Selected N-(2-phthalimidoethyl)-phthalazinones were converted into corresponding 2-[2-(methylamino) ethyl]- derivatives in satisfactory yields by treatment with hydrazine.  相似文献   

2.
Abstract

The reaction of compound 1 with triethyl orthoformate afforded 2, which in turn reacted with CS2 and active methlyene compounds or malononitrile to give dithiolane and 4-malononitrile methylene derivatives 3,4, respectively. Treatment of compound 4 with active methylene compounds afforded spiro cyclopentene derivatives 5a-c. Compound 1 was reacted with bromomalononitrile or CS2 and halocompounds to afford furo-. thieno- and dithiolano-pyrazole derivatives 6–11, respectively. The reaction of compound 12 with phenacyl bromide or benzylidenemalononitrile furnished oxathiol-2-ylidene and pyridinethione derivatives 13,14, respectively. The dibromo derivative 16 was reacted with CS2 and active methylenes or malononitrile to obtain spiro dithietanes 17a-e and 4-dicyano-methlyene derivative 22, respectively. Compounds 17 underwent a cycloaddition reaction with thioglycolic acid, N-phenylbenzohydrazindoyl bromide, 2,5-dimethylfuran and 1-phenyl-3,5-pyrazolidinedi one to give cycloadducts 18–21, respectively. Treatment of > o-aminothiophenol or o-phenylenediamine with the dicyano compound 22 leads to the formation of spiro thiazepine or spiro diazine derivatives 23a,b . The arylidene derivatives 24 was reacted with S,S-acetals, N,S-acetals or ammonium dithiocarbamate to afford dithiane, oxazine or pyrazolodithiocarbamate derivatives 25–29, respectively. Chemoselective cyclization of compound 29 with H2SO4, NaOH or MeI gave compounds 30–32, respectively. Benzopyrano derivatives 34,36 were obtained through the reaction of compound 1 with a mixture of thiourea, triethyl orthoformate and ethyl cyanoacetate or with cyanoketene S,S diacetals, respectively.  相似文献   

3.
The 3(2H)-oxo-, 3(2H)-thioxo- or 3-amino-pyridazine derivatives 4, 6 and 7 were coupled with N-phthalyl- or N-tosyl-amino acids in one-step using N,N′-dicyclohexyl-carbodiimide as the condensing agent to furnish the corresponding 3-(N-phthalyl- or N-tosyl-aminoacyl)pyridazine derivatives 8–10 respectively. Hydrazinolysis of the N-phthalyl derivatives in methanol yielded the corresponding unprotected derivatives 11–13. The antibacterial activities of the prepared compounds were tested.

  相似文献   

4.
ABSTRACT

Cyclic ketones 1a-f reacted with mercaptoacetic acid in benzene and/or toluene in the presence of p-toluenesulfonic acid afforded the corresponding spiro-1,3-oxathialanone derivatives (2a-f). Compounds 2a-f reacted with glucosamine hydrochloride in a mixture of pyridine and ethanol to yield 3-(2′-glucosyl)-2-spiro[1′-cycloalkyl]thiazolidin-4-one derivatives 4a-f. Reaction of 4a-f with fused sodium acetate in a mixture of acetic anhydride and acetic acid gave annulated spirothiazoloxazologlucose derivatives 6a-f. All the synthesized spiro derivatives were identified by conventional methods (IR, 1H NMR spectroscopy and elemental analyses).  相似文献   

5.
Abstract

5-Anthracenylidene- and 5-(4-benzyloxy-3-methoxy)benzylidene-hydantoin and 2-thiohydantoin derivatives 3a-g were prepared by condensation of anthracene-9-carboxaldehyde and 4-benzyloxy-3-methoxybenzylaldehyde with hydantoin and 2-thiohydantoin derivatives. Compounds 3a, b, f undergo Mannich reaction with formaldehyde and morpholine to give the corresponding Mannich products 4a–c. For the synthesis of alkylmercaptohydantoin 5a–o, the potassium salt of compounds 3a, b, e, f were reacted with an alkylhalide, either methyl iodide, phenacyl bromide, ethyl bromo acetate, allyl bromide, or methallyl bromide, under stirring at room temperature to afford the alkylmercaptohydantoins 5a–o. Acid hydrolysis of compounds 5a–c afforded the corresponding arylidene-hydantoin derivatives 3c, d, g. 2-Methylmercapto-hydantoin derivatives 5a, c were reacted with some secondary amines such as morpholine or piperidine to afford 5-(4-benzyloxy-3-methoxy)benzylidene-2-morpholino- or piperidino glycocyamidine derivatives 7a, 5-anthracenylidene-2-morpholin-, or piperidino glycocyamidine derivatives 7b, c.

Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file.

GRAPHICAL ABSTRACT  相似文献   

6.
Hany M. Dalloul 《合成通讯》2013,43(10):1847-1856
The reaction of 4-amino-5-phenyl-3,5-thiaaza-4-pentenoic acid 3 with various nitrilimines 2 led to the formation of substituted carboxymethylthio derivatives of 1,2,4-triazoles (4a–l) rather than the amino derivatives 5 or imidazole derivatives 6. The spectral data of the synthesized compounds are in full agreement with its molecular structure.  相似文献   

7.
Abstract

2,3,4,6-Tetra-O-acetyl-D-glucopyranose (1) was successfully transformed to an anomeric mixture of 2,3,4,6-tetra-O-acetyl-1-O-(methylthio)thiocarbonyl-D-glucopyranose (2) by liquid - liquid and solid - liquid phase transfer methods. Similar anomeric free sugar derivatives bearing acetyl or benzoyl protective groups were also smoothly converted to the corresponding 1-O-(methylthio)thiocarbonyl derivatives. Thermal rearrangement of 1-O-(methylthio)thiocarbonylfuranose derivatives proceeded well to give 1-S-methylthiocarbonyl-1-thiofuranose derivatives.  相似文献   

8.
《合成通讯》2012,42(2):256-270
Abstract

A synthesis of novel hybrid molecules containing thiazole or bis(thiazoles) each bearing benzofuran and/or benzo[d]thiazole moieties by the reaction of the appropriate thioamide derivatives with the corresponding bis-bromoacetyl derivatives is reported. Mono- and bis(triazolothiadiazine) derivatives based on benzofuran or benzo[d]thiazole moieties were also synthesized in good yields by the reaction of the appropriate bis(bromoacetyl) derivatives with each of 4-amino-5-mercapto-1,2,4-triazoles and their corresponding bis-derivatives.  相似文献   

9.
ABSTRACT

-The reaction of 3-(1-adamantyl)-4-methyl-1,2,4-triazole-5-thiol 1 with certain 2-aminoethyl chlorides in alkaline medium yielded a separable mixture of the S-(2-aminoethyl) derivatives 2 and the N-(2-aminoethyl) derivatives 3. Meanwhile, alkylation of 2-(1-adamantyl)-1,3,4-oxadiazole-5-thiol 4 with 2-aminoethyl chlorides under the same conditions yielded only the S-alkyl derivatives 5. Interaction of 4 with primary or secondary amines and formaldehyde solution yielded the corresponding N-aminomethyl derivatives in high yields.  相似文献   

10.
This article describes the synthesis of new N-functionalized perfluoroalkanesulfonamides (5) with two sulfonamides functionalities. Perfluoroalkanesulfonyl fluoride underwent a reaction with 2-chloroethylamine hydrochloride or 3-bromopropylamine hydrobromide to give N-(2-chloroethyl or 3-bromopropyl) perfluoroalkanesulfonamides (1). Reaction of (1) with potassium thiocyanate gave N-(2-thiocyanatoethyl or 3-thiocyanatopropyl) perfluoroalkanesulfonamides (3). The sulfonyl chloride derivatives (4) were prepared by reaction of 3 with sulfuryl chloride. In the last step, 4 reacted with ammonia to give the bis sulfonamides derivatives (5). The structures of all new compounds prepared were determined by 1H, 19F, and 13C NMR spectroscopies and by HR-MS.  相似文献   

11.
《合成通讯》2013,43(22):3557-3567
A simple and easy method is provided for the synthesis of the novel pyridinone derivatives (3a–e), (8a–c) and (10a–c) by the reaction of ketene acetals (2a–e), (7a–c) and (9a–c) with ethyl cyanoacetate respectively. Compounds (3b–d) reacted with triethyl orthoformate to afford the pyridinone derivatives (4-6) respectively. Compound 7a reacted with ethyl acetoacetate or diethyl malonate to give thiazolopyridinone derivative 11 or 12 respectively.  相似文献   

12.
Enehydrazine derivatives have been obtained by the reaction of 6-phenyl-1,2,4-triazine 4-oxide with pyrazolones 2, which on further heating with pyrazolones 2 are converted into the corresponding symmetrical or unsymmetrical derivatives of dipyrazolylmethane. Enehydrazine derivatives of 1,3-dimethyl-5-nitrosouracil and 1,3-dimethylimidazolidine interact with 3-methyl-1-phenyl-5-pyrazolone (2a) with the formation of dipyrazolylmethane derivative. On interacting compound 2a or 3-methyl-1-(p-nitrophenyl)-5-pyrazolone with 3,6-diphenyl-1,2,4-triazine 4-oxide 12 the corresponding 4,4'-bispyrazolones are formed, but the interaction of compound 12 with 3-(p-nitrophenyl)-1-phenyl-5-pyrazolone leads to dipyrazolylmethane derivative. Dipyrazolylmethane derivative is obtained on heating of fervenulin 4-oxide, 2,4-dihydroxy-5-nitropyrimidine, and 1,3,5-triazines: 6-azauracil, 5-azauracil, azacytosine, and 2,4-diamino-s-triazine with pyrazolone 2a.  相似文献   

13.
Condensation of substituted 2-hydroxybenzaldehyde derivatives (1a-1) with diethyl 2-pentenedicarboxylate (2) in the presence of piperidine gave coumarin and / or chromene derivatives. Attempted reaction of 4-N,N-diethylamino-2-hydroxybenzaldehyde (1a) and 2-hydroxy-3-nitrobenzaldehyde (1i) with diethyl 3-phenyl-2-pentenedicarboxylate (5) led to formation of no coumarin or chromene derivative.  相似文献   

14.
Naphthyldiene derivatives,1-4, carrying electron-donating groups at one end and electron-withdrawing groups at the other, were synthesized to study the photoisomerization process. All the compounds showed efficient photoisomerization upon direct excitation leading to the formation of 4-Z isomer with high selectivity. Triplet sensitization studies indicated inefficientE-Z isomerization process. Room temperature fluorescence of1 and2 displayed fine structure in hexane solvent and the same was replaced by broad or structureless fluorescence in acetonitrile and methanol solvents. A mechanism involving a polarized or charge transfer singlet excited state is proposed for the observed photoisomerization in these naphthyldiene derivatives.  相似文献   

15.
以豆腐果苷为原料, 与取代苯甲酰肼反应生成中间体4-β-D-吡喃阿洛糖苷-苯甲醛取代苯甲酰腙(2a2g), 在溴作催化剂的条件下发生关环反应, 合成了一系列豆腐果苷类似物3a3g. 所有化合物结构经IR, 1H NMR以及MS谱得以证实. 初步药理实验结果表明, 化合物3a, 3c, 3f与豆腐果苷相比有更好的镇静活性.  相似文献   

16.
New pyridine derivatives bearing p-dimethyl amino phenyl and p-bromophenyl moieties at position-4 and 6 have been prepared. The behavior of pyridone derivative 2 toward ethyl chloroacetate followed by hydrazine hydrate gave pyridinyl acetohydrazide derivative 7, and its behavior toward carbon electrophiles has been investigated by its reaction with aromatic aldehydes, ethyl acetoacetate, acetyl acetone, cyclohexanone, phthalic anhydride, maleic anhydride, and isatin affording the pyridine derivatives 8a–e to 16, respectively. Treatment of compound 2 with acrylonitrile in Et3N, yielded the N- alkylated derivative 17. Some pyrazole derivatives have been synthesized by interaction of the chalcone 1 with hydrazine hydrate afforded pyrazole derivative 18. Treatment of compound 18 with benzoyl chloride and or acetic anhydride resulted in the formation of the acylated compounds 19 and 20. Elemental and spectroscopic pieces of evidence characterized all the newly synthesized compounds. Some of the synthesized compounds were tested for their antibacterial activities against Gram-positive and Gram-negative bacteria.  相似文献   

17.
2-Cyano-N-(tetrahydrocarbazole)acetamide (1) was utilized for the synthesis of several new arylazocarbazole derivatives (2a–e). Compound (1) reacted with phenyl isothiocyanate to yield the corresponding non-isolable intermediate (3), which gave, upon treatment with dilute hydrochloric acid, thiocarbamoyl derivative (4). Compound (3) reacted with chloroacetone, chloroacetic acid, chloroacetyl chloride, ethyl bromoacetate, and phenacyl bromide to afford thiazolone derivatives (6), (8), and (10), respectively. Compound (1) was heated in the presence of pyridine and/or hydrazine hydrate and/or isatine to give the corresponding tetrahydrocarbazole derivatives (13), (14), and (18), respectively.

Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file.  相似文献   

18.
新型四硫富瓦烯硫杂冠醚衍生物的合成   总被引:4,自引:0,他引:4  
在高度稀释条件下, 经4,5-二溴甲基-1,3-二硫杂环戊烯-2-硫酮(7)和多缩乙二醇的1,ω-二巯基衍生物的缩合反应, 方便地合成了4,5-位带二硫杂冠醚残基的2-硫代-1,3-二硫杂环戊烯的衍生物8a8d, 中间体硫杂冠醚8c8d的合成中有明显的“模板效应”. 在亚磷酸三乙酯存在下, 8a8d经自偶联生成新型的对称双臂四硫富瓦烯(TTF)硫杂冠醚衍生物10a10d, 而与4,5-二甲硫基-1,3-二硫杂环戊烯-2-酮(9)经交叉偶联生成新型的非对称单臂四硫富瓦烯硫杂冠醚衍生物11a11d. 用循环伏安法研究了上述目标化合物的电化学性质和离子传感性质.  相似文献   

19.

Bis[thieno(3,2-b)-1,4-diazepine] (4) and bis[imidazo(1′,2′)thieno(3,2-b)-1,4-diazepine (7) derivatives were prepared starting with thieno(2,3-b)thiophenes (1) and (2), respectively. Also, benzodiazepine derivatives (11a–f) were prepared via a reaction of cyclohexenone carboxylates (8a–f) with cyclohexylamine and chloroacetyl chloride followed by cyclization. Also, dibenzoazepines (13) and (14a,b) were prepared via a reaction of (8a) with o-phenylenediamine and o-aminophenol or o-aminothiophenol.  相似文献   

20.
A new series of coumarin derivatives (2–5) was synthesized by reaction of phenylsulfonylacetonitrile (1) with 2-hydroxy-1-naphthaldehyde and/or salicyaldehyde. Compounds 3 and 5 were converted to the corresponding phenanthridine analogs 6 and 7, respectively. Compound 9a was treated with different dienophiles to furnish the endo adducts of compounds (11ad) rather than the exo adducts. Ab initio calculations at the Hartree-Fock (HF) level using the basis set 6-31 G (d,p) was used to study and validate the stereospecificity of compounds 11a–d and showed clearly that the endo adducts were thermodynamically favorable. PM3 parameters also showed that the endo adducts are thermodynamically and kinetically favorable. Tetrahydrobenzochromenone (11) was synthesized and allowed to react with different aromatic diazonium salts to give the corresponding 4-arylazo derivatives (13), which were converted to the corresponding diazaindenophenanthrene derivatives (14) by reaction with o-diamines.  相似文献   

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