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1.
Synthesis and Structural Characterization of Pyrrole Heterocyclic Systems Bearing Amino Acid Units: Novel Pyrrol‐3‐ones,Pyrrolo[1,2‐a][3,1]benzoxazines,and Pyrrolo[2,1‐b][1,3]oxazoles
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İrfan Koca Mustafa Saçmacı Filiz Yılmaz Şevket Hakan Üngören 《Journal of heterocyclic chemistry》2014,51(1):212-218
Furan‐3‐one derivatives 1 were converted into 2‐hydroxy‐pyrrole‐3‐ones 4 by reacting with various α‐ and β‐amino acids. In contrast, the reaction of furan‐3‐ones and 1‐aminocyclobutanecarboxylic acid afforded spiro‐pyrrolo[2,1‐b][1,3]oxazoles 5 via the pyrrole‐3‐one intermediate under the same reaction conditions. Some of 2‐hydroxy‐pyrrole‐3‐ones 3 derived from anthranilic acids were transformed to pyrrolo[1,2‐a][3,1]benzoxazines via intramolecular esterification. 相似文献
2.
A series of 2‐alkylthio‐4‐oxo‐3‐quinazolineacetonitriles 4 and 2‐alkylthio‐4‐oxothieno[3,2‐d]pyrimidine‐3‐acetonitriles 8 was prepared. Upon treatment with sodium hydride, compounds 4 and 8 react to give 2‐amino‐4,9‐dihydro‐9‐oxopyrrolo[2,1‐b]quinazoline‐1‐carbonitriles 9 and 6‐amino‐4,9‐dihydro‐9‐oxopyrrolo[1,2‐a]thieno[3,2‐d]pyrimidine‐7‐carbonitriles 10 , respectively. The transformation of compounds 4 and 8 to the tricyclic aminonitriles 9 and 10 involves a dimerization step followed by a pyrrole cyclization. The tert‐butyl ester derivatives 4d and 8d upon treatment with sodium hydride underwent a Thorpe‐Ziegler cyclization to provide enaminoesters of fused 1,3‐thiazines ( 16 and 17 , respectively) as major products. 相似文献
3.
An efficient and practical one‐pot procedure for the direct chemoselective synthesis of isobenzofuran and spiro[isobenzofuran‐1,2′‐pyrrole] derivatives is developed via oxidative cleavage of 3a,8b‐dihydroxyindeno[1,2‐b]pyrrol‐4‐ones with Pb(OAc)4 at room temperature. 相似文献
4.
Shanpeng Wen Weidong Cheng Pengfei Li Shiyu Yao Bin Xu Hui Li Yajun Gao Zilong Wang Wenjing Tian 《Journal of polymer science. Part A, Polymer chemistry》2012,50(18):3758-3766
Three donor–acceptor (D–A) 1,3‐di(thien‐2‐yl)thieno [3,4‐c]pyrrole‐4,6‐dione‐based copolymers, poly{9,9‐dioctylfluorene‐2,7‐diyl‐alt‐1,3‐bis(4‐hexylthien‐2‐yl)‐5‐octylthieno[3,4‐c]pyrrole‐4,6‐dione}, poly{N‐(1‐octylnonyl)carbazole‐2,7‐diyl‐alt‐1,3‐bis(4‐hexylthien‐2‐yl)‐5‐octylthieno[3,4‐c]pyrrole‐4,6‐dione}, and poly {4,8‐bis(2‐ethylhexyloxyl) benzo[1,2‐b:3,4‐b′]dithiophene‐alt‐1,3‐bis(4‐hexylthien‐2‐yl)‐5‐octylthieno[3,4‐c] pyrrole‐4,6‐dione} were synthesized by Suzuki or Stille coupling reaction. By changing the donor segment, the bandgaps and energy levels of these copolymers could be finely tuned. Cyclic voltammetric study shows that the highest occupied molecular orbital (HOMO) energy levels of the three copolymers are deep‐lying, which implies that these copolymers have good stability in the air and the relatively low HOMO energy level assures a higher open‐circuit potential when they are used in photovoltaic cells. Bulk‐heterojunction photovoltaic cells were fabricated with these polymers as the donors and PC71BM as the acceptor. The cells based on the three copolymers exhibited power conversion efficiencies of 0.22, 0.74, and 3.11% with large open‐circuit potential of 1.01, 0.99, and 0.90 V under one sun of AM 1.5 solar simulator illumination (100 mW/cm2). © 2012 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2012 相似文献
5.
Giovanni Grassi Massimiliano Cordaro Giuseppe Bruno Francesco Nicol 《Helvetica chimica acta》2002,85(1):196-205
The structures of 6‐methyl‐4,8,9‐triphenyl‐2‐oxa‐3,7‐diazaspiro[4.4]nona‐3,6‐dien‐1‐one ( 3 ) and N‐[(2‐Methyl‐4,5‐diphenyl‐1H‐pyrrole‐3‐carbonyl)oxy]benzamide ( 4 ) were established by X‐ray crystal‐structure analysis. A significant improvement in the procedure currently available for the synthesis of these compounds is described. Ab initio and DFT calculations were carried out on the compound 4 and its precursor 3 , and compared with X‐ray results. In particular, to relate structural features to biological properties, the conformational characteristics and rotational barrier of compound 4 were studied. 相似文献
6.
Rodrigo Abonia Braulio Insuasty Jairo Quiroga Heinz Kolshorn Herbert Meier 《Journal of heterocyclic chemistry》2001,38(3):671-674
The reaction of 1‐(2‐aminophenyl)pyrrole with aromatic or heteroaromatic aldehydes in ethanol and catalytic amounts of acetic acid leads to 4,5‐dihydropyrrolo[1,2‐a]quinoxalines in high yields. When aliphatic aldehydes were used under the same conditions, a slow oxidation to the corresponding pyrrolo[1,2‐a]quinoxalines can occur; the oxidation can be avoided by preparing in situ the 5‐acetyl derivatives of the 4,5‐dihydropyrrolo[1,2‐a]quinoxalines. 相似文献
7.
A series of π‐conjugated polymers and copolymers containing 1,4‐dioxo‐3,6‐diphenylpyrrolo[3,4‐c]pyrrole (also known as 2,5‐dihydro‐3,6‐diphenylpyrrolo[3,4‐c]pyrrole‐1,4‐dione) (DPP) and 1,4‐phenylene units in the main chain is described. The polymers are synthesised using the palladium‐catalysed aryl‐aryl coupling reaction (Suzuki coupling) of 2,5‐dihexylbenzene‐1,4‐diboronic acid with 1,4‐dioxo‐2,5‐dihexyl‐3,6‐di(4‐bromophenyl)pyrrolo[3,4‐c]pyrrole and 1,4‐dibromo‐2,5‐dihexylbenzene in different molar ratios. Soluble hairy rod‐type polymers with molecular weights up to 21 000 are obtained. Polymer solutions in common organic solvents such as chloroform or xylene are of orange colour (λmax = 488 nm) and show strong photoluminescence (λmax = 544 nm). The photochemical stability is found to be higher than for corresponding saturated polymers containing isolated DPP units in the main chain. Good solubility and processability into thin films render the compounds suitable for electronic applications. 相似文献
8.
Synthesis of 2‐(o‐nitrophenyl)‐6‐arylthiazolo[3,2‐b]‐[1,2,4]‐triazoles 4 and its isomer 3‐(o‐nitrophenyl)‐5‐arylthiazolo[2,3‐c]‐[1,2,4]‐triazoles 6 has been achieved starting from the appropriate 1‐(o‐nitrobenzoyl)‐3‐thiosemicarbazide 1 . Compound 1 on condensation with α‐haloketones gives 2‐(o‐nitrobenzoyl)hydrazino‐4‐arylthiazole hydrobromide 5 , which, on cyclization with POCl3, affords thiazolo[3,2‐b]‐[1,2,4]‐triazoles 6 and not the isomeric thiazolo[3,2‐b]‐[1,2,4]‐triazoles 4 . This has been established by an unequivocal synthesis of 4 through polyphosphoric acid cyclization of 5‐aroylmethylmercapto‐3‐o‐nitrophenyl‐[1,2,4]‐triazole 3 . Compound 3 was synthesized by condensation of α‐haloketones with 5‐mercapto‐3‐(o‐nitrophenyl)‐[1,2,4]‐triazole 2 , obtained cyclization of 2‐(o‐nitrobenzoyl)hydrazinecarbothioamide 1 with NaOH. The antibacterial and antifungal activities of some of the compounds have also been evaluated. 相似文献
9.
Dr. Mariusz Tasior Dr. Małgorzata Czichy Prof. Mieczysław Łapkowski Prof. Daniel T. Gryko 《化学:亚洲杂志》2018,13(4):449-456
Dibenzothienopyrrolo[3,2‐b]pyrrole and the corresponding bis(S,S‐dioxide) were synthesized by using a concise synthetic strategy. Despite the presence of six fused aromatic rings, π‐expanded pyrrolo[3,2‐b]pyrroles of this type absorb and emit at relatively short wavelengths, which reflects inefficient π conjugation due to the angular arrangement of the aromatic rings. They exhibit interesting and complex electrochemical behavior, which highlights their potential in organic electronics. Both heteroacenes undergo two‐stage oxidation while retaining the independence of each 1‐phenyl‐1H‐[1]benzothieno[3,2‐b]pyrrole, which was proved by in situ electron spin resonance measurements. Interestingly, electrochemically generated dicationdiradicals are not only distributed over the pyrrolo[3,2‐b]pyrrole scaffold, but also over the phenyl substituents located on nitrogen atoms. 相似文献
10.
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
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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
11.
K. Venkata Rao M. Raghu Prasad A. Raghuram Rao 《Journal of heterocyclic chemistry》2014,51(Z1):E380-E383
An efficient and environmentally benign one‐pot method has been developed for the synthesis of 4‐amino‐5‐arylpyrrolo[2,3‐d]pyrimidines. Phthalimido acetophenones were reacted with cyanoacetamide to give 2‐amino‐4‐phenyl‐1H‐pyrrole‐3‐carboxamides, which were further converted to 5‐aryl‐3H‐pyrrolo[2,3‐d]pyrimidin‐4‐ones. A novel method is also developed for the synthesis of 4‐amino‐5‐iodopyrrolo[2,3‐d]pyrimidines. 相似文献
12.
Synthesis and Biological Activity of Novel Ethyl Esters of 4‐R‐6,8‐Dimethyl‐1‐oxo‐1,2‐dyhidropyrrolo[1,2‐d][1,2,4]triazine‐7‐carboxylic Acids
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Valeriia Astakhina Maxim Voievudskyi Olexander Kharchenko Vladimir Novikov Elena Komarovska‐Porohnyavets Olena Petukhova 《Journal of heterocyclic chemistry》2016,53(2):421-428
The novel heterocyclizations of ethyl 5‐(hydrazinocarbonyl)‐2,4‐dimethyl‐1H‐pyrrole‐3‐carboxylate are developed. New derivatives of ethyl esters of 4‐R‐6,8‐dimethyl‐1‐oxo‐1,2‐dyhidropyrrolo[1,2‐d][1,2,4]triazine‐7‐carboxylic acids were obtained. The in vitro anticancer and antibacterial activities of the synthesized compounds were revealed. The most potent antibacterial compound appeared to be 1.3 inhibiting Staphylococcus aureus. Pyrrolo[1,2‐d][1,2,4]triazine 2.15 showed significant antifungal activity against Candida tenuis. The anticancer activity of the synthesized compounds was determined. 相似文献
13.
《Journal of heterocyclic chemistry》2018,55(1):91-96
Reaction of 5,6‐dihydro‐4H‐pyrrolo[3,2,1‐ij]quinoline‐1,2‐dione ( 1 ) with two equivalents of some 6‐aminouracils (or 6‐amino‐2‐thiouracil) generates spirocyclic tetrahydrobenzo[if]quinolizines ( 7 ). The one‐pot, three‐component reaction of amido ketone ( 1 ) with 6‐aminouracil (or 6‐amino‐2‐thiouracil) and a cyclic six‐membered 1,3‐diketone produces spirocyclic tetrahydropyrrolo[3,2,1‐ij]quinolinones ( 15 ). 相似文献
14.
Treatment of 2‐bromoaryl pyrrole/indol‐2‐yl ketones with cesium carbonate in DMF resulted in the formation of 9H‐pyrrolo[1,2‐a]indol‐9‐ones and 10H‐indolo[1,2‐a]indol‐10‐ones in moderate to excellent isolated yields. 相似文献
15.
Ethyl 1‐ethyl‐7‐methyl‐4‐oxo‐1,4‐dihydro[1,8]naphthyridine‐3‐carboxylate ( 1 ), precursor of nalidixic acid, has been converted in two steps through ([1,8]naphthyridin‐3‐yl)carbonylguanidine derivatives into substituted pyrimido[4,5‐b] and [5,4‐c][1,8]naphthyridines. 相似文献
16.
Thieno[3,4‐c]pyrrole‐4,6‐dione‐3,4‐difluorothiophene Polymer Acceptors for Efficient All‐Polymer Bulk Heterojunction Solar Cells
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Dr. Shengjian Liu Dr. Zhipeng Kan Dr. Simil Thomas Federico Cruciani Prof. Jean‐Luc Brédas Prof. Pierre M. Beaujuge 《Angewandte Chemie (International ed. in English)》2016,55(42):12996-13000
Branched‐alkyl‐substituted poly(thieno[3,4‐c]pyrrole‐4,6‐dione‐alt‐3,4‐difluorothiophene) (PTPD[2F]T) can be used as a polymer acceptor in bulk heterojunction (BHJ) solar cells with a low‐band‐gap polymer donor (PCE10) commonly used with fullerenes. The “all‐polymer” BHJ devices made with PTPD[2F]T achieve efficiencies of up to 4.4 %. While, to date, most efficient polymer acceptors are based on perylenediimide or naphthalenediimide motifs, our study of PTPD[2F]T polymers shows that linear, all‐thiophene systems with adequately substituted main chains can also be conducive to efficient BHJ solar cells with polymer donors. 相似文献
17.
Dijana Pei Ivana Ozimec Landek Renata Rup
i Marina Modri Iva Dapo Rudolf Trojko Mladen Merep Milan Mesi 《Journal of heterocyclic chemistry》2012,49(2):243-252
The present review focuses on dibenzo[b,f]oxepin‐10(11H)‐one ( I , X = O) and dibenzo[b,f]thiepin‐10(11H)‐one ( I , X = S) as common synthons in the efficient synthesis of various dibenzoxepino[4,5‐ and dibenzothiepino[4,5]‐fused five‐membered heterocycles: [2,3] fused thiophene ( II ), [3,4] fused thiophene ( III ), furan ( IV ), pyrrole ( V ), imidazole ( VI ), pyrazole ( VII ), oxazole ( VIII ), and thiazole ( IX ). The potential of I to be converted into reactive intermediates that readily undergo heteroaromatic annulation reactions by cyclocondensation with proper binucleophiles allows formation of a range of enumerated functionalized dibenzo[e,h]azulene [4] structures ( II , III , IV , V , VI , VII , VIII , IX ). Dibenzo[e,h]azulenes as heterotetracyclic scaffold can be exploited in further modifications to obtain compounds with altered physicochemical and biological profile. J. Heterocyclic Chem., (2012). 相似文献
18.
Several pyrido[2,3‐e]pyrimidine fused with other rings have been prepared by intramolecular cyclization of 5‐(4‐chlorophenyl)‐2‐hydrazino‐benzo [6,7]cyclohepta‐[1,2‐b]pyrido[2,3‐e]pyrimidine‐4‐one ( 1 ) with acids, carbon disulfide to form triazole derivatives ( 2,4 ), halo‐ketones to give triazine derivative ( 5 ), β‐ketoesters, β‐cyanoesters, and β‐diketones to yield 2‐(1‐pyrazolyl) derivatives ( 7,9,10 ), and aldehydes to form arylhydrazone derivatives ( 11a,b ) which cyclized to form triazoles ( 12a,b ). Also, acyclic N‐nucleosides are prepared by heating under reflux 2‐hydrazino‐benzo[6,7]cyclohepta[1,2‐b]pyrido[2,3‐e] pyrimidin‐4‐one ( 1 ) with xylose and glucose to give the corresponding acyclic N‐nucleosides ( 13a,b ) which are cyclized to afford the corresponding protected tetra and penta–O‐acetate C‐nucleosides ( 14a,b ). Deacetylating of the latter nucleosides afforded the free acyclic C‐nucleosides ( 15a,b ). © 2007 Wiley Periodicals, Inc. Heteroatom Chem 18:34–43, 2007; Published online in Wiley InterScience ( www.interscience.wiley.com ). DOI 10.1002/hc.20248 相似文献
19.
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
20.
The three‐component reaction of thiazole (benzothiazole), dialkyl but‐2‐ynedioate, and isatinylidene malononitriles in toluene at 110–120°C in a sealed tube afforded a mixture of cis/trans‐isomers of functionalized diastereoisomeric spiro[indoline‐3,7′‐thiazolo[3,2‐a]pyridines] and spiro[benzo[4,5]thiazolo[3,2‐a]pyridine‐3,3′‐indolines] in good yields. Both cis‐isomers and trans‐isomers were successfully separated out and fully characterized with spectroscopy and single crystal determination. Under similar conditions, the three‐component reaction containing 2‐(1,3‐dioxo‐1H‐inden‐2(3H)‐ylidene)malononitrile resulted in spiro[indene‐2,7′‐thiazolo[3,2‐a]pyridine] derivatives. 相似文献