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1.
Alzbeta Krutosikova Miloslava Dandarova Jana Chylova Daniel Vegh 《Monatshefte für Chemie / Chemical Monthly》1992,123(8-9):807-815
Summary A number of furo[3,2-c]pyridines (4a–4d) and benzo[b]derivative (4e), as well as pyrrolo[2,3-4,5]furo[3,2-c]pyridine (8) were prepared by reaction of the corresponding iminophosphoranes, available from ethyl azidoheteroacrylates and triphenylphosphine, with phenyl isocyanate. The appropriate azidoheteroacrylates were used for the preparation of some substituted furo[3,2-b:4,5-b]dipyrroles (6). The reactions of the prepared compounds are described.
Kondensierte O-, N-Heterocyclen durch Umwandlung von Azidoacrylaten
Zusammenfassung Eine Anzahl von Furo[3,2-c]pyridinen (4a –4d), ein Benzo[b]derivat (4e) und Pyrrolo[2,3:4,5]furo[3,2-c]pyridin (8) wurden durch die Reaktion von Phenylisocyanaten mit den entsprechenden Iminophosphoranen dargestellt, die aus Ethyl-azidoheteroacrylaten und Triphenylphosphin leicht zugänglich sind. Die entsprechenden Azidoacrylate wurden zur Synthese einiger Furo[3,2-b:4,5-b]dipyrrole (6) verwendet. Die Reaktionen einiger dieser Verbindungen werden beschrieben.相似文献
2.
[reaction: see text] By taking advantage of the alpha- and gamma-activation of chloropyridines as well as palladium-mediated reactions, all four possible benzo[4,5]furopyridine tricyclic heterocycles, benzo[4,5]furo[2,3-b]pyridine, benzo[4,5]furo[2,3-c]pyridine, benzo[4,5]furo[3,2-c]pyridine, and benzo[4,5]furo[3,2-b]pyridine, are efficiently synthesized from 2-chloro-3-iodopyridine, 3-chloro-4-stannylpyridine, 4-chloro-3-iodopyridine, and 2-chloro-3-hydroxypyridine, respectively. 相似文献
3.
[reaction: see text] 2,3-Disubstituted furo[3,2-b]pyridines, 2,3-disubstituted furo[2,3-b]pyridines, and 2,3-disubstituted furo[2,3-c]pyridines are readily prepared under mild conditions via the palladium-catalyzed cross-coupling of 1-alkynes with o-iodoacetoxy- or o-iodobenzyloxypyridines, followed by electrophilic cyclization by I(2) or by PdCl(2) under a balloon of carbon monoxide. 相似文献
4.
Vclav Nmec Michaela Hylsov Luk Maier Jana Flegel Sonja Sievers Slava Ziegler Martin Schrder Benedict‐Tilman Berger Apirat Chaikuad Barbora Val
íkov Stjepan Uldrijan Stanislav Drpela Karel Sou
ek Herbert Waldmann Stefan Knapp Kamil Paruch 《Angewandte Chemie (Weinheim an der Bergstrasse, Germany)》2019,131(4):1074-1078
Reported is the identification of the furo[3,2‐b]pyridine core as a novel scaffold for potent and highly selective inhibitors of cdc‐like kinases (CLKs) and efficient modulators of the Hedgehog signaling pathway. Initially, a diverse target compound set was prepared by synthetic sequences based on chemoselective metal‐mediated couplings, including assembly of the furo[3,2‐b]pyridine scaffold by copper‐mediated oxidative cyclization. Optimization of the subseries containing 3,5‐disubstituted furo[3,2‐b]pyridines afforded potent, cell‐active, and highly selective inhibitors of CLKs. Profiling of the kinase‐inactive subset of 3,5,7‐trisubstituted furo[3,2‐b]pyridines revealed sub‐micromolar modulators of the Hedgehog pathway. 相似文献
5.
For the very first time furo[3,2-c]pyrazoles have been prepared starting from pyrazole building blocks instead from furanes. During this synthesis effort two previously unknown heterocyclic scaffolds have been discovered, the furo[3,2-c]pyrazol-6-ones and the 2-cyano-3-aminofuran-4-ones. 相似文献
6.
Sirakanyan S. N. Hakobyan E. K. Hovakimyan A. A. 《Russian Journal of Organic Chemistry》2019,55(9):1344-1350
Russian Journal of Organic Chemistry - New furo[2,3-b]pyridine and pyrido[3′,2′:4,5]furo[3,2-d]pyrimidine derivatives were synthesized from ethyl... 相似文献
7.
Anthony Chartoire 《Tetrahedron》2008,64(48):10867-10873
An efficient and rapid synthesis of furo[3,2-b]pyridine 1 is described using a one-pot Sonogashira coupling/heteroannulation sequence. Regioselective lithiation of this synthon was performed leading to various 2-substituted furo[3,2-b]pyridines. Some of them were used as substrates for short functional synthesis of polyheterocycles. 相似文献
8.
Ya. L. Garazd A. S. Ogorodniichuk M. M. Garazd V. P. Khilya 《Chemistry of Natural Compounds》2002,38(5):424-433
Substituted 5H-benzo[c]furo[3,2-g]chromen-5-ones, modified analogs of psoralen that contain a benzene ring annelated at the 5,6-position of a furo[3,2-g]chromen-7-one system, were synthesized from 3-hydroxy- 6H-benzo[c]chromen-6-ones. 相似文献
9.
Shunsaku Shiotani 《Journal of heterocyclic chemistry》1993,30(4):1035-1039
The preparation of 2-aminomethyl- 3a-d , 2-acetamidomethyl- 4a-d , 2-N,N-dimethylaminomethyl- 5a-d , 2-(1-hydroxy-2-nitroethyl)- 6a-d , 2-(1-hydroxyl-2-aminoethyl)- 7a-d and 2-(1-hydroxy-2-N,N-dimethylaminoethyl)- 8b-d derivatives of furo[2,3-b]-, furo[3,2-b]-, furo[2,3-c]- and furo[3,2-c]pyridine is described. 相似文献
10.
Imino Diels-Alder reaction of imines with 2,3-dihydrofuran or 3,4-dihydro-2H-pyran proceeded smoothly in the presence of a catalytic amount (0.5 mol %) of ytterbium triflate to afford furo[3,2-c]- and pyrano[3,2-c] quinolines conveniently in high yield. 相似文献
11.
A series of substituted furo[3,2-e][1,2,4]triazolo[4,3-c]pyrimidines and furo[3,2-e]tetrazolo[1,5-c]pyrimidines were obtained from reactions of substituted 2-dimemylamino-4-hydrazmofuro[2,3-d]pyrimidines with orthoesters or sodium nitrite in acetic acid, respectively. 相似文献
12.
Louis Mavoungou-Goms Jean Bruneton Michel Aicart 《Journal of heterocyclic chemistry》1985,22(5):1233-1236
3,4-Dicarbomethoxyfuran bearing an acetonyl or a phenacy group in the 2 position w3as prepared by pyrolysis of the dihydrocyclo adduct from methyl acetylendicarboxylate and 2-acetonyl- or 2-phenacylfuran. Condensation of 2-acetonyl-3,4-dicarbomethoxyfuran with tryptamine gave a new heteroyohimbane with a furan ring, indolo[2,3-a]furo[3,2-c]quinolizine, a potential precursor of yohimbane. Ketodiacids from saponification allow one to obtain derivatives of the following heterocyclic ring systems, namely 4H-furo[3,2-c]pyran-4-one and furo[3,2-c]pyridine. 相似文献
13.
Preparation of Furo[3,2‐c]coumarins from 3‐Cinnamoyl‐4‐hydroxy‐2H‐chromen‐2‐ones and Acyl Chlorides: A Bu3P‐Mediated C‐Acylation/Cyclization Sequence
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Chia‐Jui Lee Cheng‐Che Tsai Shao‐Hao Hong Geng‐Hua Chang Mei‐Chun Yang Dr. Lennart Möhlmann Prof. Dr. Wenwei Lin 《Angewandte Chemie (International ed. in English)》2015,54(29):8502-8505
A Bu3P‐mediated cyclization reaction of 3‐cinnamoyl‐4‐hydroxy‐2H‐chromen‐2‐ones though electrophilic addition of acyl chlorides towards the synthesis of highly functionalized furo[3,2‐c]coumarins bearing a phosphorus ylide moiety is described. These unprecedented cyclization reaction proceeds under mild reaction conditions within short reaction times (1 min to 1 h), and can be further applied in the synthesis of alkenyl‐substituted furo[3,2‐c]coumarins by the treatment with carbonyl electrophiles under basic conditions. 相似文献
14.
An efficient I2/TBHP-mediated process for the formation of furo[3,2-c]coumarins from readily available materials has been developed. This process for the formation of furo[3,2-c]coumarins is quite environmental friendly and atom-economical. 相似文献
15.
We have developed two efficient one-pot reactions to generate furo[3,2-c]coumarins and chlorofuro[3,2-c]coumarins through addition/cyclization/oxidation and chlorination. One cascade addition/cyclization/oxidation sequence of 1 with H(2)O in the presence of 20% CuCl as Lewis acid under an air atmosphere generated the 2-substituted-4 H-furo[3,2-c]chromen-4-one 2. Another sequence in the presence of 10% CuBr and excess CuCl(2) as the oxidant afforded the 3-chloro-2-substituted-4 H-furo[3,2- c]chromen-4-one 3. 相似文献
16.
Kensuke Okuda Jun‐ichi Takano Takashi Hirota Kenji Sasaki 《Journal of heterocyclic chemistry》2012,49(2):281-287
Reaction of 3‐(3‐cyanopropoxy)[1]benzofuran‐2‐carbonitriles with potassium tert‐butoxide gave 5‐amino‐1,2‐dihydro[1]benzofuro[3,2‐d]furo[2,3‐b]pyridines and 5‐amino‐2,3‐dihydro[1]benzofuro[3,2‐b]oxepin‐4‐carbonitriles as new ring systems. Reactions of the 5‐chloro derivative, obtained from 5‐amino‐1,2‐dihydro[1]benzofuro[3,2‐d]furo[2,3‐b]pyridine, produced a dihydrofuran ring‐opened compound and 5‐substituted compounds. J. Heterocyclic Chem.,(2011). 相似文献
17.
The 13C nmr spectra of 2- or 3-monosubstituted furo[2,3-b]- 1a-1j , furo[3,2-b]- 2a-2j , furo[2,3-c]- 3a-3j and furo[3,2-c]pyridine derivatives 4a-4j are reported. Effects by change in annelation and substituent effects on 13C chemical shifts and carbon-proton coupling constants are discussed. The spectra of benzo[b]furan derivatives 5a-5j having the corresponding substituent are also reported for comparison. 相似文献
18.
V. M. Lyubchanskaya L. M. Alekseeva S. A. Savina V. G. Granik 《Chemistry of Heterocyclic Compounds》2000,36(11):1276-1283
A heterocyclic quinone was used in the Nenitzescu reaction for the first time. New tricyclic compounds - pyrrolo[3,2-e]- and furo[3,2-e]indazoles - were synthesized by the condensation of 1,3-diphenyl-4,7-dioxoindazole with various enamines. 相似文献
19.
An approach to the synthesis of derivatives of new heterocyclic system, pyrido[3′,2′:4,5]-furo[3,2-c]isoquinoline, was suggested. A condensation reaction of substituted 3-cyanopyridin-2(1H)-ones with methyl 2-(chloromethyl)benzoate and subsequent treatment of the condensation product with potassium tert-butoxide leads to substituted pyrido[3′,2′:4,5]furo[3,2-c]-isoquinolin-5(6H)-ones. Similarly, a condensation reaction of substituted 3-cyanopyridin-2(1H)-ones with 2-(chloromethyl)benzonitrile and subsequent treatment of the condensation product with potassium tert-butoxide gives substituted 5-aminopyrido[3′,2′:4,5]furo[3,2-c]-isoquinolines. 相似文献
20.
A convenient synthesis of the benzo[h]furo[3,2-c]quinoline ring is reported. Hydrogenation of dienic adducts 5 gives comppounds 6. Successive pyrolysis and alcaline hydrolysis of 6 provide diacids 9 which in the presence of anhydrous ammonium acetate and acetic acid undergoes intramolecular cyclisation to give benzo[h]furo[3,2-c]quinolone derivatives 12. The modulation of the 7-carboxy group and introduction of amino groups in the 6 position are then realized. 相似文献