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1.
The novel 1,2‐diaryl substituted pyrrolo[3,4‐b]pyridine‐5,7‐diones were selectively synthesized in high yields by the base catalyzed cyclization reaction of 3‐arylamino‐1‐methyl‐1H‐pyrrole‐2,5‐diones with cinnamaldehyde and its derivatives in acetonitrile at room temperature. However, when piperidinium trifluoroacetate was employed as catalyst, the reaction afforded a mixture of 1,2‐diaryl and 1,4‐diaryl substituted pyrrolo[3,4‐b]pyridine‐5,7‐diones in comparable yields. 相似文献
2.
One‐Pot Synthesis of Novel Pyrrolo[1,2‐a]quinoxaline‐4(5H)‐ones Using Benzene‐1,2‐diamine,Acetylenedicarboxylates, and β‐Nitrostyrene Derivatives
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The reaction between a variety of o‐phenylenediamines (=benzene‐1,2‐diamines), dialkyl acetylenedicarboxylates, and derivatives of nitrostyrene (=(E)‐(2‐nitroethenyl)benzene) in the presence of sulfamic acid (SA; H3NSO3) as catalyst led to the corresponding pyrrolo[1,2‐a]quinoxaline‐4(5H)‐one derivatives in high yields. 相似文献
3.
K. Kie‐Kononowicz J. Handzlik D. Lazewska E. Pkala C. E. Müller J. Karolak‐Wojciechowska 《Journal of heterocyclic chemistry》2002,39(2):243-253
As a continuation of our studies on bicyclic heterocycles with benzodiazepine receptor affinity, derivatives with a 5:5 bicyclic skeleton, namely imidazo[2,1‐b]thiazoles, imidazo[2,1‐b]imidazoles and pyrrolo[1,2‐c]imidazoles were prepared. The compounds possessed an aromatic substituent with different spatial arrangement and distance to the bicyclic skeleton. X‐ray structure analysis was performed for Z‐2‐(4‐chlorobenzylidene)‐5,5‐diphenyl‐2,3,5,6‐tetrahydroimidazo[2,1‐b]imidazoline‐3,6‐dione ( 6a ) and 5‐amino‐6‐cyano‐7‐phenyl‐1‐oxo‐3‐thioxo‐2,3‐dihydro‐1H‐pyrrolo[1,2‐c]imidazole ( 20a ). In contrast to the previously described arylideneimidazo[2,1‐b]thiazepinones the smaller heterocyclic ring systems investigated in this study were devoid of meaningful benzodiazepine receptor affinity as well as anti‐convulsant activity. 相似文献
4.
Computational Studies on Intramolecular Cycloadditions of Azidoenynes and Azidobutenenitriles to Give 6H‐Pyrrolo[1,2‐c][1,2,3]triazoles and 5H‐Pyrrolo[1,2‐d]tetrazoles
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Gérard Audran Paul Brémond Douniazad El Abed Sylvain R. A. Marque Didier Siri Maurice Santelli 《Helvetica chimica acta》2015,98(7):1018-1027
Energetics of intramolecular cycloadditions of azidoenynes and azidobutenenitriles to give 6H‐pyrrolo[1,2‐c][1,2,3]triazoles and 5H‐pyrrolo[1,2‐d]tetrazoles have been calculated at the B3LYP/6.311++G(3df,3pd) level of theory in ideal gas and in H2O as solvent. Stabilities of the corresponding anions, tautomers, and isomers are discussed. Transition states of the cyclization of parent compounds are determined at the same level of theory. 相似文献
5.
Kazuhiro Kobayashi Taketoshi Kozuki Manami Konishi Teruhiko Suzuki Miyuki Tanmatsu Hisatoshi Konishi 《Helvetica chimica acta》2011,94(7):1234-1238
The reaction of aryl(3‐isocyanopyridin‐4‐yl)methanones 1 , easily prepared from commercially available pyridin‐3‐amine, with aryl Grignard reagents gave, after aqueous workup, 2,3‐diaryl‐3H‐pyrrolo[2,3‐c]pyridin‐3‐ols 2 . These rather unstable alcohols were O‐acylated with Ac2O in pyridine in the presence of a catalytic amount of 4‐(dimethylamino)pyridine (DMAP) to afford the corresponding 2,3‐diaryl‐3H‐pyrrolo[2,3‐c]pyridin‐3‐yl acetates 3 in relatively good yields. 相似文献
6.
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
7.
An efficient cascade process five‐component reaction of isatins and 3‐oxo‐N‐arylbutanamide for the synthesis of 4,4′‐((2‐oxoindoline‐3,3‐diyl)bis(methylene))bis(2‐aryl‐1H‐pyrrolo[3,4‐c]quinoline‐1,3(2H)‐dione) derivatives was reported under mild condition. The advantages of this strategy are easy to obtain raw materials, convenient one‐pot procedure, and simple operation. 相似文献
8.
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
9.
Samira El Ghammarti Benoít Rigo Hechmi Mejdi Jean‐Pierre Hnichart Daniel Couturier 《Journal of heterocyclic chemistry》2000,37(1):143-150
Tetrahydro‐2H‐pyrrolo[1,2‐c]quinazoline‐3‐ones are easily obtained from the Friedel‐Crafts cyclization of N‐arylaminomethyl pyroglutamic acids. This reaction occurrs via an acyliminium salt formed by decarboxylation of the acid function. 相似文献
10.
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
11.
《Journal of heterocyclic chemistry》2018,55(1):166-172
Using ionic liquids as green media, a series of 6‐arylbenzo[4,5]imidazo[1,2‐c]quinazoline derivatives is synthesized via a reaction of 2‐(1H‐benzo[d]imidazol‐2‐yl)aniline and benzaldehydes in the air. While the intermediate products of 6‐aryl‐5,6‐dihydrobenzo[4,5]imidazo[1,2‐c]quinazolines were obtained in high yields at the same conditions under nitrogen protection. 相似文献
12.
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
13.
Feng Liang Jiaxin Hu Lande Zhang Yuefei Hu Hongwen Hu 《Journal of heterocyclic chemistry》2001,38(4):853-857
An efficient two step route has been developed to synthesize pyrrolo[2,1,5‐cd]indolizine derivatives. The reaction sequence proceeds via preparation of 3‐acyl‐5‐methylindolizines followed by an intramolecular condensation. The procedures were carried out under convenient conditions and gave the products in high yields. It could be expected to be used to prepare a broad range of potentially interesting pyrrolo[2,1,5‐cd]indolizine derivatives. 相似文献
14.
《Journal of heterocyclic chemistry》2017,54(6):3440-3446
2‐(1H ‐benzo[d ]imidazol‐2‐yl)anilines reacted with haloketones including 5‐chloropentan‐2‐one and 6‐chlorohexan‐2‐one catalyzed by iodine, giving benzo[4,5]imidazo[1,2‐c ]pyrrolo[1,2‐a ]quinazoline and 6H ‐benzo[4,5]imidazo[1,2‐c ]pyrido[1,2‐a ]quinazoline derivatives, respectively. This domino‐type reaction formed two new heterocycles and three new covalent bonds in one‐pot procedure and provided a green method for the synthesis of fused pentacyclic heterocycles bearing both quinazoline and benzimidazole moieties in ionic liquids. 相似文献
15.
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
16.
《中国化学》2017,35(9):1422-1430
The base promoted three‐component reaction of β‐ enamino imide, malononitrile and various cyclic α‐ diketones in acetonitrile showed interesting molecular diversity. The reactions with acenaphthylene‐1,2‐dione and ninhydrin afforded functionalized spiro[indene‐2,4'‐pyrrolo[3,4‐b ]pyridines] and spiro[acenaphthylene‐1,4'‐pyrrolo[3,4‐b ]pyridines] in good yields. The similar reaction of phenanthrene‐9,10‐dione resulted in the formation of the unexpected complex phenanthro[9',10':4,5]furo[2,3‐c ]pyrrolo[3,4‐b ]pyrroles in satisfactory yields. 相似文献
17.
《Journal of heterocyclic chemistry》2018,55(7):1695-1701
A series of novel N‐(2‐(pyridine‐4‐yl)‐1H‐pyrrolo[3,2‐c]‐pyridin‐6‐yl‐(substituted)‐sulfonamide derivatives were synthesized from 2‐bromo‐6‐nitro‐1H‐pyrrolo[3,2‐c]pyridine through a series of reactions including Suzuki reaction, reduction, protection, and sulfonamide coupling. All the synthesized compounds were screened for anticancer activity against MCF‐7, HeLa, A‐549, and Du‐145 cancer cell lines by the MTT assay. The preliminary bioassay suggests that most of the compounds show antiproliferation with different degrees. Doxorubicin was used as a positive control. Among the synthesized compounds, 8d and 8h were most active compared with the standard in cell line data. The synthesized compounds 8d and 8h show IC50 values in the range of 1.88–5.16 μM for all the cell lines. Compounds 8d and 8h were further studied for a panel of eight human kinase at 10 μM concentrations and the result shows 64% to 70% inhibitions for both Aurora‐A and Aurora‐B kinase. 相似文献
18.
The catalytic asymmetric [3+2] cycloaddition of α‐ketoesters with 2‐nitrovinylindoles and 2‐nitrovinyl‐ pyrroles has been established. This strategy allowed the construction of structurally diverse pyrrolo[1,2‐a]indoles bearing three contiguous stereocenters in generally high yields and good to excellent stereoselectivities (up to 98% yield, > 98 : 2 dr, 99% ee). The efficient synthesis of tetracyclic psychotropic compound analogue via the derivatization of cycloadduct showed the great synthetic potential of this strategy. 相似文献
19.
Anna V. Gulevskaya Shee Van Dang Alexander F. Pozharskii 《Journal of heterocyclic chemistry》2005,42(3):413-419
Synthesis of some condensed pyrrolo‐, thieno‐, furo‐, pyrido‐ and pyranopteridines as well as isomeric pyrrolo‐ and thienopyrimido[4,5‐c]pyridazines from alkynyl derivatives of 6,8‐dimethylpyrimido[4,5‐c]pyridazine‐5,7(6H,8H)‐dione and 1,3‐dimethyllumazine is represented. 相似文献
20.
Xuerui Wang Wenxue Zhang Hongjuan Shen Wei Zhang 《Journal of heterocyclic chemistry》2013,50(3):501-505
A one‐pot synthesis of pyrrolo[1,2‐a]quinolin‐1‐ones has been developed from the reactions of 5‐hydroxy‐1‐arylpyrrolidin‐2‐ones with 1,3‐dicarbonyl compounds under the promotion of H3PO4/P2O5 or HOAc/H2SO4. The pyrrolo[1,2‐a]quinolin‐1‐ones are formed by two‐step reactions, that is, the coupling of N‐acyliminium ion intermediates produced from 5‐hydroxy‐1‐arylpyrrolidin‐2‐ones with 1,3‐dicarbonyls and subsequent Friedel–Crafts reactions of the resulting ketone with the aryl ring. 相似文献