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1.
S. M. Sherif 《Monatshefte für Chemie / Chemical Monthly》1996,127(8-9):955-962
Summary A convenientGewald synthesis of 3,5-diaminothiophene-2-carbonitrile derivatives (2) is reported. The synthetic potential of the -enaminonitrile moiety in2 has been explored; it proved to be a promising candidate for the synthesis of polyfunctionally substituted thieno[3,2-b]pyridines and thieno[3,2-d]pyrimidines.
Synthesen mit heterocyclischen -Enaminonitrilen: Eine einfache Methode zur Herstellung polyfunktionell substituierter Thiophen-, Thieno[3,2-b]pyridin- und Thieno[3,2-d]pyrimidinderivate
Zusammenfassung Eine bequeme Methode zur Herstellung von 3,5-Diaminothiophen-2-carbonitril-Derivaten (2) nachGewald wird vorgestellt. Das synthetische Potential der -Enaminonitrilfunktion von2 wurde untersucht.2 ist ein geeignetes Ausgangsmaterial für die Synthese polyfunktionell substituierter Thieno[3,2-b]pyridine und Thieno[3,2-d]pyrimidine.相似文献
2.
V. A. Artemov V. L. Ivanov L. A. Rodinovskaya A. M. Shestopalov V. P. Litvinov 《Chemistry of Heterocyclic Compounds》1996,32(4):483-486
1,4-Dihydro-3-cyano-2-pyridinethiolates react with 2-bromo-l-(4-bromophenyl)ethylidenemalononitrile or N-cyanochloracetanudine to give 6, 9-dihydropyrido[3, 2': 4, 5]thieno[3. 2-b]pyridines or 6, 9-dihydropyrido-[3.2:4.5Jthieno(3,2-d]pyrimidines, respectively.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 553–556, April, 1996. 相似文献
3.
The synthesis of N‐substituted pyridothienopyrimidines bearing ethoxymethyl, benzyloxymethyl, methylthiomethyl, benzoylmethyl, allyl, sec‐butyl, and 2‐acetyloxyethyl chains as a sugar mimic was described. The O‐substituted pyridothienopyrimidines were obtained during some reactions. 相似文献
4.
N‐Alkylation of 10H‐9‐fluoropyrido[3,2‐b][1,4]‐benzothiazine 5a, 10H‐7‐fluoropyrido[3,2‐b][1,4]‐benzothiazine 5b, and 10H‐7‐chloropyrido[3,2‐b][1,4]‐benzothiazine 5c with different N‐(bromoalkyl)phthalimides using anhydrous K2CO3 and tetrabutylammonium bromide (TBAB) under dry conditions with microwave irradiation leads to the formation of 10‐(phthalimidoalkyl)‐halosubstitutedpyrido[3,2‐b][1,4]‐benzothiazine (6a–f) along with some unidentified product. Compound 5a is a new azaphenothiazine derivative and was obtained from hitherto unknown 2‐acetylamino‐3‐fluorophenyl‐3′‐nitro‐2′‐pyridylsulfide 4a via Smiles rearrangement. Compound 4a is required for the synthesis and has been prepared starting from 2‐amino‐3‐fluorobenzenethiol 1a in three steps. 相似文献
5.
Yagodkina-Yakovenko M. S. Bol’but A. V. Vovk M. V. 《Russian Journal of Organic Chemistry》2018,54(10):1569-1572
Russian Journal of Organic Chemistry - Methyl 2-(bromomethyl)thiophene-3-carboxylates reacted with substituted 2-hydroxybenzonitriles to give methyl... 相似文献
6.
A convenient procedure for the synthesis of 2‐spirobenzopyranoquinone 5 and its application to the preparation of spironaphtho[2,3‐b]pyranoquinones 6 and 7 is described. 相似文献
7.
Nirmal D. Desai 《合成通讯》2013,43(15):2169-2182
Some new 7,9‐substituted 7H‐1,2,3,4‐tetrazolo[1,5‐c]pyrrolo[3,2‐e]pyrimidines 5 have been synthesized either by diazotization of 4‐hydrazino‐5,7‐disubstituted‐7H‐pyrrolo[2,3‐d]pyrimidines 4 obtained by hydrazinolysis of 4‐chloro‐5,7‐disubstituted 7H‐pyrrolo[2,3‐d]pyrimidines 3 or via a substitution reaction between 3 and sodium azide. 5,7‐Disubstituted‐7H‐pyrrolo[2,3‐d]pyrimidin‐4(3H)‐ones 2 were obtained by cyclocondensation of 1,4‐disubstituted 2‐amino‐3‐cyanopyrroles 1 with formic acid, which, on chlorination using phosphorus oxychloride, afforded 3. 2‐Amino‐3‐cyanopyrroles 1 were synthesized from the reaction between (2-bromo-1-(4-fluorophenyl) ethylidene) propanedinitrile and substituted aromatic amines under Gewald reaction conditions. A novel route for the synthesis of 4‐amino‐5,7‐disubstituted‐7H‐pyrrolo[2,3‐d]pyrimidines 6 by the reductive ring cleavage of 5 has been reported. 相似文献
8.
Reaction between 6‐(un)substituted‐2‐thiouracils and E‐ethyl 4‐bromocrotonate under basic conditions at room temperature is an easy, mild, high‐yielding, and regioselective method for the preparation of 7‐(un)substituted dihydrothiazolo[3,2‐a]pyrimidinone derivatives. 相似文献
9.
Dyachenko I. V. Dyachenko V. D. Dorovatovsky P. V. Khrustalev V. N. Nenajdenko V. G. 《Russian Journal of Organic Chemistry》2020,56(6):974-982
Russian Journal of Organic Chemistry - 2-Acyl-4,5,6-trialkyl-3-aminothieno[2,3-b]pyridines,... 相似文献
10.
4‐Mercaptothiocoumarin was alkylated with different propargylic and allylic halides under phase‐transfer‐catalyzed conditions in the presence of tetrabutylammonium bromide (TBAB) or benzyl triethylammonium chloride (BTEAC) catalyst in dichloromethane–aqueous NaOH solution (1%) at room temperature. These 4‐thiopropynyl and thioallyl thiocoumarins were then refluxed in chlorobenzene and quinoline to give thiopyrano[3,2‐c][1]benzothiopyran‐5(2H)‐one and thiopyrano[3,2‐c][1]benzothiopyran‐4‐one respectively. 相似文献
11.
Mohamed A. A. Elneairy Mohamed A. M. Gad-Elkareem Azza M. Abdel-Fattah 《Phosphorus, sulfur, and silicon and the related elements》2013,188(6):1451-1466
Pyrdine-2(1H)-thione 1 reacted with ethyl chloroacetate 2 to give 2-S-ethoxy-carbonylmethylpyridine derivative 3, which could be cyclized into thieno[2,3-b]-pyridine-2-carbohydrazide derivative 5 by boiling with hydrazine hydrate. The latter compound reacted with cinnamonitrile derivatives 6a, b, triethylorthoformate, formic acid, dimethylformamide-dimethylacetal, and diethyl carbonate to give the corresponding shiff base 7a, b and pyrido[3′,2′;-4,5]thieno[3,2-d]pyrimidine derivatives 10–13 in respective manner. On the other hand, compound 5 also reacted with carbondisulphide and phenyl isothiocyanate to afford the corresponding 2-(1,3,4-oxadiazolo-2-yl)thieno[2,3-b]pyridine derivatives 18 and 22. Finally, compound 5 reacted with some β-dicarbonyl compounds, such as ethyl acetoacetate, acetylacetone and ethyl β-arylazoacetoacetate, to yield the corresponding 2-(pyrazol-1-yl-carbonyl)thieno[2,3-b]pyridine derivatives 24, 25, and 27 respectively. 相似文献
12.
《合成通讯》2013,43(7):1265-1275
Abstract 4‐Mercapto‐6‐methyl‐2‐pyrone was alkylated with different allylic and propargylic halides under phase transfer catalyzed condition in the presence of TBAB or BTEAC catalyst in chloroform–aqueous NaOH (1%) at room temperature. The S‐alkylated thiopyran‐2‐ones were then refluxed in quinoline or in chlorobenzene to give 4‐chloromethylthiopyrano[2,3‐b]pyran‐2‐one and 4‐hydroxymethylthiopyrano[2,3‐b]pyran‐2‐one or several thieno[2,3‐b]pyran‐2‐ones. 相似文献
13.
14.
We have obtained dihydrofurans 3a–j in the radical cyclization of 4‐hydroxycoumarin 1a and 2‐hydroxy‐1,4‐naphtoquinone 1b with electron rich alkenes 2a–i by manganese(III) acetate. Methods A and B, which have different molar ratios were studied comparatively in these reactions, and we observed that method B (molar ratio 2:1:3) gave the best results. Treatment of 4‐hydroxycoumarin 1a and electron rich alkenes 2a–e gave 2,3‐dihydro‐4H‐furo[3,2‐c]chromen‐4‐ones 3a–e in 36–86% yields by the method B. Under the same conditions, the reactions of 2‐hydroxy‐1,4‐naphtaquinone 1b with conjugated alkenes 2b and 2f–i afforded 2,3‐dihydronaphtho[2,3‐b]furan‐4,9‐diones 3f–j in an excellent yields. 相似文献
15.
Safiyyah A. H. Al-Waleedy Etify A. Bakhite Mohamed S. Abbady Hajjaj H. M. Abdu-Allah 《Journal of heterocyclic chemistry》2020,57(6):2379-2388
3-Cyano-5-ethoxycarbonyl-6-methyl-4-styrylpyridine-2(1H)-thione ( 3 ) was prepared by reaction of 2-cyano-5-phenylpenta-2,4-dienethioamide ( 2 ) with ethyl acetoacetate or by multicomponent reaction of cinnamaldehyde ( 1 ), cyanothioacetamide and ethyl acetoacetate in a moderate yield. Reaction of compound 3 with some N-aryl-2-chloroacetamides, in the presence of sodium acetate, gave the corresponding 2-(N-arylcarbamoylmethylsulfanyl)-3-cyano-5-ethoxycarbonyl-6-methyl-4-styrylpyridines 4a-f . When compounds 4a-f were subjected to Thorpe-Ziegler reaction conditions, they converted into the corresponding 3-amino-5-ethoxycarbonyl-2-(N-arylcarbamoyl)-6-methyl-4-styrylthieno[2,3-b]pyridines 5a-f . Compounds 5a,e,f were reacted, in turn, with 2,5-dimethoxytetrahydrofuran to furnish the corresponding 3-(pyrrol-1-yl)thieno-pyridines 6a,e,f . Reactions of 5a-f with triethyl orthoformate or nitrous acid were also carried out and their products were identified. Structural formulas of all synthesized compounds was characterized and confirmed on the basis of their elemental and spectral analyses. 相似文献
16.
A. A. Aly 《Phosphorus, sulfur, and silicon and the related elements》2013,188(12):3079-3096
Possible approaches to the synthesis of functionalized, pyrimido[5′,4′:4,5]thieno [3,2-c]pyridazines 2-18 , pyridazino[3′,4′:4,5]thieno[2,3-d]triazines 19, 20a,b and pyrido[3′,2′:4,5]thieno[3,2-c]pyridazines 22a,b are described. The sequence involves the heterocyclization of 6-amino-1,3-diphenyl-1,4-dihydrothieno[3,2-c]pyridazine-7-carboxamide (1) with appropriate reagents. The antimicrobial activity of some the newly synthesized compounds was examined. All tested compounds proved to be active as antibacterial and antifungal agents. 相似文献
17.
Different novel phthalazino[2,3‐b]phthalazine‐5,7,12,14‐tetraones were synthesized in a simple and environmentally benign method from the reaction of phthalic anhydrides with semicarbazide or thiosemicarbazide using montmorillonite K‐10 clay as solid heterogeneous acidic catalyst and microwaves under solvent‐free conditions in good yields and short reaction times. Products were characterized by the elemental analysis, IR, NMR, and mass spectrometry. 相似文献
18.
Mikhail V. Dorogov Sergey A. Ivanovsky Maria Y. Khakhina Dmitry V. Kravchenko Sergey E. Tkachenko 《合成通讯》2013,43(23):3525-3535
Sulfochlorination of 2‐оxo‐2,3,4,5‐tetrahydro‐1H‐benzo[b]azepine led to regioselective formation of the corresponding 7‐chlorosulfonyl derivative. Starting from this reagent, a large number of substituted 2‐oxo‐7‐sulfamoyl‐2,3,4,5‐tetrahydro‐1H‐benzo[b]azepines were obtained. This approach is amenable to combinatorial production of the title compounds, which possess promising therapeutic potential. 相似文献
19.
Reaction of 4‐hydroxy‐6‐methyl‐2(1H)‐pyridones 1a and 4‐hydroxy‐1,6‐dimethyl‐2(1H)‐pyridones 1b with diethyl malonates 2a–e leads to the formation of pyrano[3,2‐c]pyridines 4a–j. Degradation of 4a–i affords the corresponding ketones 6a–i. Condensation of ketones 6a–i with hydroxyl amine or phenyl hydrazine hydrochloride is described. 相似文献
20.
A methodology, based on tandem [2,3] and [3,3] sigmatropic rearrangement, has been described for the synthesis of hitherto unreported, potentially bioactive pyrrolo[3,2‐c][1]benzothiopyran‐4‐ones (6a–g) derivatives. 相似文献