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1.
Design,Synthesis of Novel Thiourea and Pyrimidine Derivatives as Potential Antitumor Agents 下载免费PDF全文
1,3‐Bis‐(arylidene)thiourea derivatives ( 11a‐c ) were prepared by reacting thiourea ( 9 ) with bezaldehyde, p‐chlorobenzaldehyde or p‐anisaldehyde ( 10a‐c ) respectively. Further reaction of ( 11b ) with acetyl acetone, ethyl acetoacetate, malononitrile and acetic anhydride gave tetrahydropyrimidine‐2‐thiones ( 12‐14 ) and 1,3‐diacetyl thiourea ( 15 ). Compound ( 11b ) reacted with chloroacetyl chloride to give the corresponding pyrimidin‐4‐one derivative ( 16 ). Reaction of ( 12‐14 ) with acetic acid in aqueous sodium nitrite yielded the corresponding oxime derivatives ( 17‐19 ). The triazole ( 20 ) was achieved via refluxing of ( 19 ) in dimethylformamide. Reaction of ( 16 ) with mercaptoacetyl chloride gave the sulfanyl‐acetic acid ( 21 ) which afforded the dihydrazinyl ( 22 ) up on treatment with hydrazine hydrate. Newly synthesized compounds ware characterized by elemental analyses and spectral data (IR, 1H‐NMR, 13C‐NMR and mass spectra). The investigated compounds were screened for their cytotoxicity, i.e. compounds 19 , 20 and 22 exhibited highly potential antitumor activity. 相似文献
2.
Synthesis,Reactions, and Pharmacological Evaluations of Some Novel Pyridazolopyridiazine Candidates 下载免费PDF全文
Ahmed A. Fayed Naif O. Al‐Harbi Abd El‐Galil E. Amr Atef A. Kalmoush Khalid A. Shadid Eman M. Flefel 《Journal of heterocyclic chemistry》2014,51(6):1770-1777
Herein, we report the synthesis, characterization, and preliminary pharmacological activity of a new series of substituted pyrazolopyridazine derivatives. Compound 1 was reacted with ethoxymethylene malononitrile 2 in refluxing ethanol to give the corresponding compound 3 , which was treated with hydrazine hydrate or formamide to give pyrazolo[3,4‐c]pyrazole 4 and pyrazolo pyrimidine 5 derivatives, respectively. Also, compound 3 was reacted with NH4SCN or carbon disulphide or ethyl acetoacetate to yield the corresponding pyrazolo derivatives 6 , 7 , 8 , respectively. Additionally, compound 3 was reacted with triethyl orthoformat in acetic anhydride to give 9 , which was treated with hydrazine hydrate to give hydrazino derivative 10 . The latter compound transformed into the pyrazolo[4,3‐e][1,2,4]triazolo[1,5‐c]‐pyrimidine 11 via refluxing with acetic anhydride. Finally, compound 9 was reacted with benzoic acid hydrazide or mercapto acetic acid to give compounds 12 and 13 , respectively. The latter compound was treated with refluxing ethanolic sodium ethoxide solution to afford the pyrazolothiazolopyrimidine 14 . Some of the compounds exhibited better activities as anti‐inflammatory and antimicrobial agents than the reference controls. The detailed synthesis, spectroscopic data, anti‐inflammatory, and antimicrobial activities of the synthesized compounds was reported. 相似文献
3.
SA Al-Issa 《Molecules (Basel, Switzerland)》2012,17(9):10902-10915
The reaction of 4-methyl-2-phenyl-1,2-dihydro-6-oxo-5-pyridine- carbonitrile (1) with arylidene malononitrile afforded isoquinoline derivatives 2a,b. 6-Chloro-4-methyl-2-phenyl-5-pyridinecarbonitile (3) obtained by chlorination of compound 1 with phosphoryl chloride was converted into 6-amino-4-methyl-2-phenyl-5-pyridinecarbonitrile (4) and 6-hydrazido-4-methyl-2-phenyl-5-pyridinecarbonitrile (5) in good yield, through reactions with ammonium acetate and hydrazine hydrate, respectively. Treatment of 4 with ethyl acetoacetate, acetic anhydride, formic acid, urea and thiourea gave the corresponding pyrido [2,3-d] pyrimidine derivatives 7-10a,b. A new series of 6-substituted-4-methyl-2-phenyl-5-pyridine carbonitriles 11-13 has been synthesized via reaction of 4 with phenyl isothiocyanate, benzenesulphonyl chloride and acetic anhydride. Treatment of 4 with malononitrile gave 1,8-naphthyridine derivative 14. The reactivity of hydrazide 5 towards acetic acid, phenylisothiocyanate and methylacrylate to give pyrazolo-[3,4-b]-pyridine derivatives 15-17 was studied. Treatment of 5 with acetic anhydride, phthalic anhydride and carbon disulphide gave pyridine derivatives 18,19 and 1,2,4-triazolo-[3,4-a]-pyridine derivative 20. 相似文献
4.
Ahmed A. El-Maghraby Gameel A. M. El-Hag Ali Ahmed H. A. Ahmed Mohamed S. A. El-Gaby 《Phosphorus, sulfur, and silicon and the related elements》2013,188(2):293-302
Ternary condensation of aromatic aldehydes, malononitrile and thioglycolic acid (2:2:1 molar ratio) in ethanol/piperidine afforded the corresponding thiazolo[3,2-a]pyridines 1a-d . Thiazolo[2',3':1,6]pyrido[2,3-d]pyrimidine 4 was obtained by refluxing of compound 1a with acetic anhydride. Also, thiazolopyrido pyrimidine 6 was produced by refluxing of 1a with triethylorthoformate followed by treatment with hydrazine hydrate. Refluxing 1a with formic acid yielded the thiazolopyridopyrimidine 8 which on chlorination with thionyl chloride furnished the chloro derivative 9 . Finally, amino thiazolo[2',3':1,6]pyrido[2,3-d]pyrimidine 10 was obtained by treatment of 1a with formamide. The structures of these compounds were established on the basis of elemental analyses, IR, 1 H NMR, and mass spectral data. Also, the antimicrobial activity of some synthesized compounds is reported. 相似文献
5.
A. B. A. El-Gazzar H. A. R. Hussein A. S. Aly 《Phosphorus, sulfur, and silicon and the related elements》2013,188(12):2771-2784
We prepared a thieno[2,3-d]pyrimidine compound fused with a thiazolo ring to produce biologicaly active compounds. In a one-step reaction, 2-arylmethylene derivative (3) was prepared via the reaction of a ternary mixture of 2-thioxo-1,2,3,4-tetrahydrocyclohepteno[4,5]thieno[2,3-d]pyrimi-dine-4-one (2), cloroacetic acid, and a proper aldehyde. The reaction of 2 with 3-chloropent-2,4-dione in ethanolic potassium hydroxide yielded the S-acetylacetone derivative 4e. The latter compound reacted with hydrazine hydrate and phenyl hydrazine to give 2-pyrazolthio derivatives 8a,b, respectively. Compound 4e also underwent cyclization on boiling with acetic anhydride/pyridine solution to form 2-acetyl-3-methyl thiazolo[3,2-a]cyclohepteno[4,5]thieno[2,3-d] pyrimidine-5-one (9). To support the structure 9, it gave a characteristic reaction for the 2-acetyl group. The 2-methylthio derivatives 4a underwent further alkylation at N3 to give 6a,b. The purpose of the synthesis of thienopyrimidine derivatives is due to high biological activities. The 4-oxo-thienopyrimidine derivatives acted as inhibitors of adenosine kinase, platelet aggregation, antilukemia, and anticancer activities. 相似文献
6.
Mohamed A. A. Elneairy 《Phosphorus, sulfur, and silicon and the related elements》2013,188(2):469-483
Pyridine-2(1H)-thione 5 was synthesized from the reaction of 3-[3-(4-chlorophenyl)-1-phenyl-1H-pyrazol-4-yl]-1-phenylpropenone (3) and cynothioacetamide (4). Compound 5 reacted with halogented compounds 6a–e to give 2-S-alkylpyridine derivatives 7a–e, which could be in turn cyclized into the corresponding thieno[2,3-b]-pyridine derivatives 8a–e. Compound 8a reacted with hydrazine hydrate to give 9. The latter compound reacted with acetic anhydride (10a), formic acid (10b), acetic acid, ethyl acetoacetate, and pentane-2,4-dione to give the corresponding pyrido[3′,2′:4,5]thieno-[3,2-d]pyrimidine 13a,b, pyrazolo[3′,4′:4,5]thieno[3,2-d]pyridine 14 and thieno[2,3-b]-pyridine derivatives 18 and 20, respectively. Alternatively, 8c reacted with 10a,b and nitrous acid to afford the corresponding pyrido[3′,2′:4,5]thieno[3,2-d]pyrimidine 24a,b and pyrido[3′,2′:4,5]thieno[3,2-d][1,2,3]triazine 26 derivatives, respectively. Finally compound 5 reacted with methyl iodide to give 2-methylthiopyridine derivative 27, which could be reacted with hydrazine hydrate to yield the corresponding pyrazolo[3,4-b]-pyridine derivative 29. 相似文献
7.
Abu‐Bakr A. A. M. El‐Adasy Ahmed A. Khames Mohamed A. M. Gad‐Elkareem 《Journal of heterocyclic chemistry》2013,50(1):42-48
2‐Aminopyridine‐3‐carbonitrile derivative 1 reacted with each of malononitrile, ethyl cyanacetate, benzylidenemalononitrile, diethyl malonate, and ethyl acetoacetate to give the corresponding [1,8]naphthyridine derivatives 3 , 5 , 8 , 11 , and 14 , respectively. Further annulations of 3 , 5 , and 8 gave the corresponding pyrido[2,3‐b][1,8]naphthyridine‐3‐carbonitrile derivative 17 , pyrido[2,3‐h][1,6]naphthyridine‐3‐carbonitrile derivatives 18 and 19 , respectively. The reaction of 1 with formic acid, formamide, acetic anhydride, urea or thiourea, and 4‐isothiocyanatobenzenesulfonamide gave the pyridopyrimidine derivatives 20a , b , 21 , 22a , b , and 26 , respectively. Treatment of compound 1 with sulfuric acid afforded the amide derivative 27 . Compound 27 reacted with 4‐chlorobenzaldehyde and 1H‐indene‐1,3(2H)‐dione to give the pyridopyrimidine derivative 28 and spiro derivative 30 , respectively. In addition, compound 1 reacted with halo compounds afforded the pyrrolopyridine derivatives 32 and 34 . Finally, treatment of 1 with hydrazine hydrate gave the pyrazolopyridine derivative 35 . The structures of the newly synthesized compounds were established by elemental and spectral data. 相似文献
8.
Mohamed M. Abdulla 《Monatshefte für Chemie / Chemical Monthly》2008,139(1):69-76
Summary. A series of substituted heterocyclic systems were prepared from N
1-[4-(2-thienylmethylene)phenyl]-5-chloro-2-methoxybenzamide, which was prepared from the corresponding 5-chloroanisic acid
(2-methoxy-4-chlorobenzoic acid) as starting material. Condensation of the thienylmethylene derivative with guanidine hydrochloride,
urea, or thiourea afforded the aminopyrimidine, pyrimidinone, and thioxopyrimidine derivatives. The latter was condensed with
chloroacetic acid to yield a thiazolopyrimidine, which was condensed with 2-thiophenealdehyde to yield the arylmethylene derivative,
however, it was also prepared directly from thiopyrimidine by the action of chloroacetic acid, 2-thiophenealdehyde, and anhydrous
sodium acetate. Treating of the thienylmethylene derivative with phenylhydrazine or hydrazine hydrate in dioxane afforded
N-phenylpyrazoline and a pyrazoline, which was reacted with acetyl chloride in dioxane affording the N-acetyl analogue. The thienylmethylene derivative was reacted with malononitrile or ethyl cyanoacetate in the presence of
ammonium acetate to yield the corresponding cyanoaminopyridine and cyanopyrimidone derivatives. Also, it was reacted with
hydroxylamine hydrochloride in pyridine to give the oxime derivative, which was cyclized with acetic anhydride. On the other
hand, condensation of the thienylmethylene derivative with ethyl cyanoacetate in the presence of sodium ethoxide or cyanothioacetamide
gave the cyanopyrane and pyridine thione derivative, which was treated with ethyl chloroacetate affording the ethyl carboxylate
derivative. The pharmacological screening showed that many of these compounds have good anti-arrhythmic activity and low toxicity. 相似文献
9.
Mohamed M. Abdulla 《Monatshefte für Chemie / Chemical Monthly》2008,15(9):69-76
A series of substituted heterocyclic systems were prepared from N
1-[4-(2-thienylmethylene)phenyl]-5-chloro-2-methoxybenzamide, which was prepared from the corresponding 5-chloroanisic acid
(2-methoxy-4-chlorobenzoic acid) as starting material. Condensation of the thienylmethylene derivative with guanidine hydrochloride,
urea, or thiourea afforded the aminopyrimidine, pyrimidinone, and thioxopyrimidine derivatives. The latter was condensed with
chloroacetic acid to yield a thiazolopyrimidine, which was condensed with 2-thiophenealdehyde to yield the arylmethylene derivative,
however, it was also prepared directly from thiopyrimidine by the action of chloroacetic acid, 2-thiophenealdehyde, and anhydrous
sodium acetate. Treating of the thienylmethylene derivative with phenylhydrazine or hydrazine hydrate in dioxane afforded
N-phenylpyrazoline and a pyrazoline, which was reacted with acetyl chloride in dioxane affording the N-acetyl analogue. The thienylmethylene derivative was reacted with malononitrile or ethyl cyanoacetate in the presence of
ammonium acetate to yield the corresponding cyanoaminopyridine and cyanopyrimidone derivatives. Also, it was reacted with
hydroxylamine hydrochloride in pyridine to give the oxime derivative, which was cyclized with acetic anhydride. On the other
hand, condensation of the thienylmethylene derivative with ethyl cyanoacetate in the presence of sodium ethoxide or cyanothioacetamide
gave the cyanopyrane and pyridine thione derivative, which was treated with ethyl chloroacetate affording the ethyl carboxylate
derivative. The pharmacological screening showed that many of these compounds have good anti-arrhythmic activity and low toxicity. 相似文献
10.
M. M. Ghorab N. E. Amin M. S. A. El Gaby N. M. H. Taha M. A. Shehab I. M. I. Faker 《Phosphorus, sulfur, and silicon and the related elements》2013,188(12):2918-2928
The key intermediate diisothiocyanate 2 was allowed to react with 5-amino-3-methyl-pyrazole-4-carbonitrile 3, ethyl 5-amino-1-phenyl-pyrazole-4-carboxylate 6, 2-amino-tetrahydrobenzo[b]thiophene-3-car-bonitrile 9, ethyl-2-amino-tetra-hydrobenzo[b]thiophene-3-carboxylate 12, and/or 1,2,4-triazole 15 to give the corresponding biscompounds 4, 5, 7, 8, 10, 11, 13, 14, and 16, respectively. The structure of the synthesized compounds was elucidated by elemental analyses and spectral data. Some of the prepared compounds were tested for their antimicrobial and antitumor activities. 相似文献
11.
《合成通讯》2012,42(2):185-196
AbstractA series of some pyrrolone derivatives were synthesized from the acid hydrazide, derived from a pyrazolyl-2(3H)-furanone, through treating with some carbonyl reagents such as 1-phenyl-3-(thiophen-2-yl)-1H-pyrazole-4-carbaldehyde, formic acid, lauroyl chloride, succinoyl chloride, propionic anhydride, as well as, ethoxymethylene malononitrile. All compounds were obtained in good yields and characterized by their microanalytical and spectral data. The synthesized products were evaluated for their in vitro antitumor activity against two human carcinoma cell lines (HCT-116 and MCF7) using doxorubicin as a reference drug by MTT assay. The results revealed that some compounds exhibited significant potency. Noteworthy, the N-propionyl hydrazide derivative was the most potent against both cell lines. 相似文献
12.
Ahmed F. A. Shalaby Mohamed M. Abdulla Abd El Galil E. Amr Azza A. Hussain 《Monatshefte für Chemie / Chemical Monthly》2007,138(10):1019-1027
Summary. A series of substituted heterocyclic systems were prepared from N1-[4-(4-fluorocinnamoyl)phenyl]-5-chloro-2-methoxybenzamide, which was prepared from the corresponding 5-chloroanisic acid
(2-methoxy-4-chlorobenzoic acid) as starting material. Treating of the cinnamoyl derivative with hydrazine hydrate in dioxane
afforded a pyrazoline, which was reacted with morpholine and paraformaldehyde to give the N-substituted pyrazoline. Acylation of pyrazoline with acetyl chloride in dioxane afforded the N-acetyl analogue. Also, the cinamoyl derivative was reacted with methylhydrazine, phenylhydrazine, or ethyl cyanoacetate to
yield the corresponding N-methyl-, N-phenylpyrazoline, pyrane, and pyridone derivatives. Condensation of the cinnamoyl derivative with cyanothioacetamide gave
the pyridinethione derivative, which was treated with ethyl chloroacetate affording the ethyl carboxylate derivative. Also,
it was reacted with malononitrile or ethyl acetoacetae to give the cyano amino analougues and ethyl carboxylate, which was
reacted with methylhydrazine to give the (indazolyl)phenyl derivative. On the other hand, reaction of cinnamoyl derivative
with acetyl acetone afforded the cyclohexenyl derivative, which was reacted with hydrazine hydrate to give the [methylindazolyl]phenyl
derivative. Condensation of the cinnamoyl derivative with guanidine hydrochloride or thiourea afforded the aminopyrimidine
derivative and thioxopyrimidine. The latter was condensed with chloroacetic acid to yield a thiazolopyrimidine, which was
condensed with 2-thiophenealdehyde to yield the arylmethylene derivative, however, it was also prepared directly from thiopyrimidine
by the action of chloroacetic acid, 2-thiophenealdehyde, and anhydrous sodium acetate. The pharmacological screening showed
that many of these compounds have good anti-arrhythmic activity and low toxicity. 相似文献
13.
Saad R. Atta-Allah Rasha S. Gouhar Magdy M. Hemdan Wael S. I. Abou-Elmagd Kamal A. A. Kandeel 《合成通讯》2017,47(4):299-309
6-Aminopyrazolo[1,2-a][1,2,4]triazine-4,8-dione derivative 3 was obtained upon the reaction of the acid hydrazide derivative 2a with ethyl cyanoacetate. The reactions of 3 with several electrophiles such as aldehydes, isatin, acetic anhydride, phenyl isocyanate, benzoyl isothiocyanate, and p-toluenesulfonyl chloride were studied. The structures of the newly synthesized compounds were established on the basis of IR, 1H NMR, mass spectra, and elemental analyses. The antitumor activities of some selective compounds were examined against two cell lines as liver carcinoma cell line (HEPG-2) and human breast cancer cell line (MCF7). 相似文献
14.
Galal H. Sayed Mohammad E. Azab Kurls E. Anwer 《Journal of heterocyclic chemistry》2019,56(8):2121-2133
Under both conventional and microwave methods, 2‐amino‐4H‐pyran‐3‐carbonitrile derivative 1 was synthesized and reacted with different reagents. Thus, 2‐amino‐4H‐pyran‐3‐carbonitrile derivative was treated with chloroacetyl chloride, phenyl isocyanate, cyanoacetic acid, benzoyl chloride, triethyl orthoformate, acetic anhydride/H2SO4, arylidene malononitrile, urea, and/or p‐aminosulphaguanidine producing chloroacetamide, 3‐phenylurea, cyanoacetamide, N‐benzoylpyran, ethylformimidate, pyranopyrimidin‐4‐one, pyranopyridine, pyranopyrimidin‐2‐one, and pyranopyrimidin‐2‐imine derivatives, respectively. Meanwhile, compound 1 was reacted with ethyl bromoacetate, phenacyl bromide, phthalic anhydride, different aromatic amines, and/or acetic acid/H2SO4 to produce 5‐aminopyrano[2,3‐b]pyrrole‐6‐carboxylate, dihydropyrano[2,3‐b]pyrrole‐6‐yl‐(phenyl)methanone, 1,3‐dioxoisoindolinyl pyran, 1,4‐dihydropyridine, and 2‐hydroxy‐1,4‐dihydropyridine derivatives, respectively. On the other hand, when compound 1 was allowed to react with maleic anhydride and/or hydrazine hydrate, pyran‐4‐oxobut‐2‐enoic acid and 3‐aminopyranopyrazole derivatives were obtained, respectively. Reaction of pyran‐4‐oxobut‐2‐enoic acid with malononitrile under different conditions gave 2‐(furan‐2‐yl)‐4H‐pyran and 2‐(4H‐pyran‐2‐yl)‐1H‐pyrrole derivatives, while condensation of 3‐aminopyranopyrazole with benzaldehyde gave 1,4‐dihydropyrano[2,3‐c]pyrazol‐3‐yl‐1‐phenylmethanimine derivative. The newly synthesized compounds were characterized by the spectroscopic tools IR, 1H‐NMR, 13C‐NMR, MS, and elemental analysis. Some of these compounds have been screened in vitro for antimicrobial activity against different strains of bacteria and fungi and also were tested against two cancer cell lines: mammary gland breast cancer (MCF‐7) and colon cancer (HCT‐118). 相似文献
15.
F. F. Abdel-Latif R. M. Shaker S. A. Mahgoub M. Z. A. Badr 《Journal of heterocyclic chemistry》1989,26(3):769-772
The reaction of 3-hydrazino[1, 2, 4]triazino[5, 6-b]indole I with nitrous acid affords the azide III which could be cyclized with acetic anhydride to 10-acetyl-10H-tetrazolo[5′,1′:3, 4][1, 2, 4]triazino[5, 6-b]indole IIb . Cyclization reactions of I with acetic anhydride, ethyl chloroformate, carbon disulphide and aromatic aldehydes to the corresponding fused triazolo derivatives V–VIII are reported. On the other hand cyclization reactions of I with malononitrile, ethyl cyanoacetate, ethyl acetoacetate and acetylacetone to the corresponding condensed pyrazolino derivatives IX–XI are also reported. The reaction of I with α-dicarbonyl compounds to form mono and dihydrazones are reported. The structure of the compounds prepared and their cyclization mechanisms are reported. 相似文献
16.
α,β,γ,δ-四-{4-[3-(9-(4-(3-(9-(4-(2-(5,5-二酰氧基甲基-1,3-二噁烷基))))苯基-2,4,8,10-四氧杂螺[5.5]十一烷基)))苯基-2,4,8,10-四氧杂螺[5.5] 十一烷基]}苯基卟啉星形化合物的合成 总被引:1,自引:1,他引:0
以对苯二甲醛、丙二腈、季戊四醇和吡咯为原料, 合成了含有螺环结构单元的中间体3-[4-(2,2-二氰基)乙烯基]苯基-9-(4-甲酰基)苯基-2,4,8,10-四氧杂螺[5.5]十一烷(3)和α,β,γ,δ-四-(4-甲酰基苯基)卟啉(4). 4与过量的季戊四醇反应, 得到α,β,γ,δ-四-{4-[2-(5,5-二羟甲基-1,3-二噁烷基)]}苯基卟啉(5), 5与3的反应产物经10% NaOH 处理后, 再与过量的季戊四醇反应, 得到α,β,γ,δ-四-{4-[3-(9-(4-(3-(9-(4-(2-(5,5-二羟甲基-1,3-二噁烷基))))苯基-2,4,8,10-四氧杂螺[5.5]十一烷基)))苯基-2,4,8,10-四氧杂螺[5.5]十一烷基]}苯基卟啉(6), 6与乙酐、丙酐、苯甲酰氯反应, 得到α,β,γ,δ-四-{4-[3-(9-(4-(3- (9-(4-(2-(5,5-二乙酰氧基甲基-1,3-二噁烷基))))苯基-2,4,8,10-四氧杂螺[5.5]十一烷基)))苯基-2,4,8,10-四氧杂螺[5.5]十一烷基]}苯基卟啉(7), α,β,γ,δ-四-{4-[3-(9-(4-(3-(9-(4-(2-(5,5-二丙酰氧基甲基-1,3-二噁烷基))))苯基-2,4,8,10-四氧杂螺[5.5]十一烷基)))苯基-2,4,8,10-四氧杂螺[5.5]十一烷基]}苯基卟啉(8)和α,β,γ,δ-四-{4-[3-(9-(4-(3-(9-(4-(2-(5,5-二苯甲酰氧基甲基-1,3-二噁烷基))))苯基-2,4,8,10-四氧杂螺[5.5]十一烷基)))苯基-2,4,8,10-四氧杂螺[5.5]十一烷基]}苯基卟啉(9)等三种卟啉星形化合物. 中间体1~6和星形化合物7~9均进行了IR, 1H NMR, MS和元素分析等结构表征. 对影响反应的诸因素进行了讨论. 相似文献
17.
Peter Gajdoš Soňa Pavlíková Filip Bureš Alžbeta Krutošíková 《Central European Journal of Chemistry》2005,3(2):311-325
The synthesis and reactions of methyl 2-[3-(trifluoromethyl)phenyl]-4H-furo[3,2-b]pyrrole-5-carboxylate (1a) are described. Upon reaction with methyl iodide, benzyl chloride, or acetic anhydride, this compound gave N-substituted products 1b-d. By hydrolysis of compounds 1a-c, the corresponding acids 2a-c were formed, or by reaction with hydrazine-hydrate, the corresponding carbohydrazides 3a-c were formed. By heating 2-[3-(trifluoromethyl)phenly]-4H-furo[3,2-b]pyrrole-5-carboxylic acid (2a) in acetic anhydride, 4-acetyl-2-[3-(trifluoromethyl)phenyl]furo[3,2-b]pyrrole (4) was formed. By hydrolysis of 4, 2-[3-(trifluoromethyl)phenyl]-4H-furo[3,2-b]pyrrole (5a) was formed, and reactions with methyl iodide or benzyl chloride gave N-substituted products 5b-c. The reaction of 4 with dimethyl butynedioate gave substituted benzo[b]furan 6. Compound 3a reacted with triethyl orthoesters giving 7a-c, which afforded with phosphorus (V) sulphide the corresponding thiones 8a-c. The thiones 8a-c reacted with hydrazine hydrate to form hydrazine derivatives 9a-c. The reaction of triethyl orthoformiate with compounds 9a-c led to furo[2′,3′: 4,5]pyrrolo[1,2-d][1,2,4]triazolo[3,4-f][1,2,4]triazines 10a-c. Hydrazones 11a-c were formed from 3a-c and 5-[3-(trifluoromethyl)phenyl]furan-2-carboxaldehyde. The effect of microwave irradiation on some condensation reactions
was compared with “classical” conditions. The results showed that microwave irradiation shortens the reaction time while affording
comparable yields. 相似文献
18.
A.-B. A. G. Ghattas A. Khodairy M. A. Abd-Rahman S. Younes 《Phosphorus, sulfur, and silicon and the related elements》2013,188(8):1781-1794
Pyrazolo[3,4-b]pyridine derivative 3a was prepared and reacted with methyl iodide to give 4 or 5 depending on reaction conditions. Oxidation of 3a with iodine produced the corresponding disulphide derivative 6 , whereas oxidation with KMnO 4 gave the corresponding oxo derivative 7 . Oxidation of 4 afforded the corresponding sulphone derivative 8 , which on boiling in NaOH solution gave 7 . The reaction of compound 3a with chloroacetonitrile, ethyl chloroacetate, phenacyl bromide, and chloroacetanilide afforded 9a , b , 11 , and 12 respectively. Cyclication of the products 9a , b , 11 , and 12 yielded 10a , b , 13 , and 14 respectively. The reaction of compound 14 with ethyl orthoformate, nitrous acid, acetic anhydride, benzaldehyde, urea, CS 2 , and phenyl isothiocyanate afforded compounds 15-21 respectively. 相似文献
19.
《Journal of heterocyclic chemistry》2017,54(4):2360-2366
Condensation of 2‐amino‐5‐phenyl‐5H‐thiazolo[4,3‐b] [1,3,4] thiadiazoles ( 1 ) with some carboxylic acid derivatives furnished corresponding compounds 2–4 , respectively. Alkylation of 1 with benzoylchloride and 4‐chlorobenzyl chloride afforded thiazolo[4,3‐b][1,3,4]thiadiazole derivatives 5 and 6 , respectively. Similarly, transformation of 1 with chloroacetyl chloride yielded chloroacetamide derivative 7 . The later compound was subjected to react with potassium thiocyanate or piperazine whereby, the binary thiazolidinone derivative 8 and N 1 ,N4‐disubstituted piperazine 9 were produced, respectively. Also, the reactivity of 1 toward various active methylene reagents was investigated. Accordingly, our attempts to synthesize the tricyclic heterocyclic system 10 , 11′ , 12 ′ by reaction of 1 with chloroacetonitrile, 4‐oxo‐4‐phenylbutanoic acid and/or diethylmalonate in presence of acetyl chloride was furnished 10 , 11 , and 12 . The newly synthesized compounds were screened as antimicrobial agent. 相似文献
20.
Azza M. Abdel-Fattah Labeeb M. Shaif Fawzy A. Attaby 《Phosphorus, sulfur, and silicon and the related elements》2013,188(10):2443-2456
The present study aimed to investigate the synthetic potentiality and chemical reactivity of 2-thioxo-1,2-dihydropyridine-3-carbonitrile derivative 1. This goal performed via its reaction with each of 1-chloroacetone and iodomethane to afford the corresponding 2-alkylthio derivatives 3 and 9, respectively. Compound 3 underwent intramolecular cyclization to afford the corresponding thieno[2,3-b]pyridine derivative 4 which in turn, reacted with dimethylformamide/dimethylacetal followed by hydrazine hydrate and nitrous acid to afford the corresponding pyridothienopyrimidine and pyridothienopyridazine derivatives 6 and 8, respectively. On the other hand, Compound 9 reacted with hydrazine hydrate to give 3-aminopyrazolo[3,4-b]pyridine derivative 10, which diazotized with nitrous acid to give the corresponding diazonium salt 11. Compound 11 coupled with several active –CH2-containing reagents to synthesize the corresponding pyridopyrazolo-triazines 15, 24, 29, and 31. The formulas of all newly synthesized heterocyclic compounds were elucidated by considering the data of IR, 1H NMR, Mass spectral data, as well as data from elemental analyses. 相似文献