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Synthesis of New Pyrrolo Heterocycles (I): Novel Synthesis of Pyrano[2,3‐c]pyrrole,Isoindoline, Pyrrolo[3,4‐b]pyridine,and Pyrrolo[3,4‐d]pyrimidine Derivatives 下载免费PDF全文
F. Z. El‐Ablak N. S. Abu‐Elenein M. A. Sofan 《Journal of heterocyclic chemistry》2016,53(6):1999-2006
Michael addition of 1,5‐diaryl‐2,3‐dioxopyrrolidine derivatives with α‐cyanocinnamonitriles and ethyl α‐cyanocinnamates afforded 4H‐pyrano[2,3‐c]pyrrole derivatives in the presence of sodium ethoxide. Under the same reaction condition, the ylidenes of 1,5‐diaryl‐2,3‐dioxopyrrolidine were reacted with malononitrile or ethyl cyanoacetate to give isoindole derivatives; however, pyrrolo[3,4‐b]pyridine derivatives were formed when cyanoacetamide was used. Moreover, pyrrolo[3,4‐d]pyrimidine derivatives were synthesized by treating 4‐benzylidene‐1,5‐diphenyl‐2,3‐dioxopyrrolidine with urea and/or thiourea under basic conditions. The structures of all the new synthesized compounds were confirmed by elemental analysis, IR and NMR spectra. 相似文献
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Mohamed A. Khalil 《中国化学会会志》2002,49(6):1069-1072
The synthesis of different substituted pyrazolo[3,4‐b]pyridines by the reaction of 3‐amino‐5‐chloro‐1‐phenylpyrazole‐4‐carboxaldehyde 1 as starting material with some active methylene reagents has been reported. 相似文献
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Antonino Lauria Patrizia Diana Paola Barraja Anna Maria Almerico Girolamo Cirrincione Gaetano Dattolo 《Journal of heterocyclic chemistry》2000,37(4):747-750
Derivatives of the new ring system pyrrolo[3,4‐e][1,2,3] triazolo[1,5‐a]pyrimidine 6 were prepared in high yields in one step by reaction of 3‐azidopyrrole 3 and substituted acetonitriles. Compound 6b rearranged, upon heating in dimethyl sulfoxide in the presence of water, to pyrrolo[3,4‐d][1,2,3]triazolo‐[1,5‐a]pyrimidine 7. 相似文献
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Sanchez-Martinez C Faul MM Shih C Sullivan KA Grutsch JL Cooper JT Kolis SP 《The Journal of organic chemistry》2003,68(21):8008-8014
Synthesis of aryl- and hetero[a]pyrrolo[3,4-c]carbazoles by photochemical oxidation and Heck cyclization are described. Photochemical oxidation of 2-naphthyl indolyl maleimide affords two different carbazole regioisomers, depending on the reaction conditions. The regiochemistry of the cyclization can be controlled using the Heck reaction. 相似文献
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5-Methylenolether derivatives of pyrrolo[3,4-a]carbazoles were obtained from cycloadditions between 3-(1-methoxyvinyl)-1-tosylindole and N-substituted maleimides. They
were transformed into the hydroxy derivatives by treatment with H2SO4, selectively reduced to the ether by H2/Pd–C, and in the imide moiety by L-Selectride?. From the analogous BOC protected indole derivative the parent α,β-unsaturated ketones were obtained, which were transformed into hydroxyimino compounds,
and which could be deprotected by heating to the melting point. Deprotection of the tosyl derivatives was not successful.
The imide part of the molecule was hydrolyzed using methanolic NaOH. The stereochemistry of all products was elucidated mainly
by spectroscopic methods, and compared with results of calculations. 相似文献
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Natalia Monakhova Svetlana Ryabova Vadim Makarov 《Journal of heterocyclic chemistry》2016,53(3):685-709
The procedures for the synthesis of substituted pyrrolo[1,2‐a]indoles and some of their biological properties are reviewed. 相似文献
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2-Thioxo-1,2-dihydropyridine derivatives 2a, 2b were reacted with methyl iodide to give 2-methylthiopyridines 3a, 3b, which were reacted with hydrazine hydrate to produce 3-aminopyrazolo[5,4-b]pyridines 4a, 4b. Compounds 4a, 4b were diazotized to afford the corresponding diazonium salts 5a, 5b, which were reacted with some active methylene compounds 6a-6h to give the corresponding pyrido[2′,3′ : 3,4]pyrazole[5,1-c][1,2,4]triazines 7-14. 相似文献
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Quinoline and isoquinoline react with 2‐(bromoacetyl)benzothiazole ( 1 ) in dry benzene to give the corresponding quinolinium and isoquinolinium salts 2 and 10 which undergo base‐mediated [3+2] 1,3‐dipolar cycloaddition with some acetylene and ethylene derivatives to give the corresponding benzothiazole‐containing pyrrolo[1,2‐a]quinoline and pyrrolo[2,1‐a]isoquinoline derivatives. 相似文献
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Fathy Abdel‐Kader Amer Metwally Hammouda Abdel‐Aziz Sayed El‐Ahl Bakr Fathy Abdel‐Wahab 《中国化学会会志》2007,54(6):1543-1552
Treatment of heterocyclic β‐ketonitriles 1a,b with hydrazine hydrate and phenylhydrazine afforded the hydrazine derivatives 2a‐d which cyclized in PPA into pyrrolo[3,4‐c]pyrazoles 3a‐d. Reaction of 1a,b with cyanoacetohydrazide furnished the cyanoacetyl pyrrolo[3,4‐c]pyrazoles 4a,b. The hydrazine 2c reacted with β‐diketone and β‐ketoesters to afford pyrazolyl‐pyrrolines 5‐7. Also the later hydrazine reacted with some D‐aldoses and aceteophenone to give the corresponding hydrazones 10‐12 and hydrazine carboxamide derivatives 15a,b respectively. 相似文献
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A sequential one‐pot two‐step reaction for efficient synthesis of pyrrolo[2,1‐a]isoquinoline and pyrrolo[1,2‐a]quinoline derivatives in good yields has been successfully developed. The reaction included firstly Cu‐catalyzed three‐component reaction of isoquinoline (quinoline), acetylenedicarboxylate and alkynylbenzene and then Pd‐catalyzed intramolecular C(sp)‐C(sp2) coupling reaction of initially formed 1‐alkenyl‐2‐alkynyl‐1,2‐dihydroisoquinoline (1,2‐dihydroquinoline). 相似文献
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Synthesis of Novel 13a‐(ω‐Aminoalkyl)‐8‐oxoberbines by Means of Reaction of Homophthalic Anhydride with 1‐Substituted 3,4‐Dihydroisoquinolines. An Unexpected Formation of a Pyrrolo[3,4‐i]berbindione 下载免费PDF全文
Elena Stanoeva Angelina Georgieva Stanislava Avramova Nikola Burdzhiev László Lázár 《Journal of heterocyclic chemistry》2015,52(1):130-135
The reaction of 1‐[ω‐(N‐acylated amino)alkyl]‐3,4‐dihydroisoquinolines ( 7a , 7b , 7c , 7d , 7e ) with homophthalic anhydride ( 1 ) leads to the formation of 8‐oxo‐13a‐[(N‐acylated amino)alkyl]‐8H‐dibenzo[a,g]quinolizine‐13‐carboxylic acids ( 8a–e ) with predomination of cis diastereomers, together with small amount of trans-8a . cis‐13a‐[(N‐Cbzaminomethyl)]‐8‐oxo‐dibenzoquinolizine‐13‐carboxylic acid ( cis-8a ) cyclized to the unknown dibenzo[a,g]pyrrolo[3,4‐i]quinolizinedione ( 10 ) upon moderate heating in methanol. 相似文献
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《中国化学》2018,36(6):519-525
A gold(I)‐catalyzed highly diastereo‐ and enantioselective intermolecular cycloaddition of oxime ethers with nitrones under mild conditions was developed, which provides an facile access to optically pure highly substituted pyrrolo[3,4‐d][1,2]oxazines. The salient features of this reaction include general substrate scope, high efficiency, high enantioselectivity, readily available starting materials, and the use of commercially available ligand. 相似文献
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Talaat I. El‐Emary 《中国化学会会志》2007,54(2):507-518
The reaction of the aminopyrazole 1 with benzenesulfonyl chloride, arenediazonium salt, chloroacetyl chloride, ethoxy methyleneamlononitrile and with ethyl 2‐cyano‐3‐ethoxyacrylate gave the substituted 3‐methyl‐1‐phenylpyrazole 2–5a,b . Compound 5b was cyclized to 6 and to 7 by treating it with AlCl3 and with POCl3, respectively. Compound 6 converted to 7 by boiling it in POCl3/PCl5. Compound 10b was produced through reaction of 9 with acetophenone. Reaction of 1 with benzylidinemalononitrile afforded 11 . New methods for preparation of 15 and 16 are described. The reaction of 8 with malononitrile, thiosemicarbazide, phenyl hydrazine and acetophenone afforded compounds 18–21 . The reaction of 21 with malononitrile gave 22 . Compounds 23–26 were produced upon reaction of 10a with malononitrile, phenyl hydrazine, thiosemicarbazide, semicarbazide and with benzaldehyde, respectively. 相似文献
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Kumaresan Prabakaran Matthias Zeller Paul S. Szalay Karam J. Rajendra Prasad 《Journal of heterocyclic chemistry》2012,49(6):1302-1309
Previously not easily accessible pyrano[2,3‐a]carbazoles were synthesized in highly convergent syntheses avoiding multistep procedures from readily available 1‐hydroxycarbazoles. Substituted pyrano[2,3‐a]carbazoles were produced by three different methods by treatment of the 1‐hydroxycarbazoles with dimethyl acetylene dicarboxylate (DMAD) and triphenylphoshine, by reaction with ethyl 2‐methylacetoacetate in the presence of ZnCl2/POCl3, and by reaction with trifluoroacetic acid followed by Wittig reaction with (carbethoxymethylene) triphenylphosphorane. The article also highlights the optimization of reaction conditions and strategies to avoid formation of byproducts for all three types of reactions. 相似文献
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The synthesis of 7,8‐dihydro‐5(6H)‐quinolinone ( 3 ) from commercially available 3‐amino‐2‐cyclohexen‐1‐one ( 1 ) and 3‐(dimethylamino)acrolein ( 4 ) in 23% yield avoids the preparation of propynal ( 2 ). Conversion of 5‐(4‐methylphenylsulfonyl)‐6,7,8,9‐tetrahydro‐5H‐pyrido[3,2‐b]azepine ( 12 ) to 6‐(4‐methylphenylsulfonyl)‐1,4,5,6‐tetrahydropyrazolo[3,4‐d]pyrido[3,2‐b]azepine ( 24 ) is described. Removal of the N‐(4‐methylphenylsulfonyl) group with 40% sulfuric acid in acetic acid gave the tricyclic azepine 26. Application of a similar series of reactions to 5‐(4‐nitrobenzoyl)‐6,7,8,9‐tetrahydro‐5H‐pyrido[3,2‐b]‐azepine ( 13 ) afforded 6‐(4‐nitrobenzoyl)‐1,4,5,6‐tetrahydropyrazolo[3,4‐d]pyrido[3,2‐b]azepine ( 25 ). 相似文献