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1.
2,3-Dihydrofuro[3,2-c]coumarin-3-one reacts with arylhydrazines via two routes. The corresponding hydrazones are formed from arylhydrazines in alcohol and nitrophenylhydrazines in acetic acid
or toluene. With phenylhydrazine and para-tolylhydrazine in toluene, 2,3-dihydrofuro[3,2-c]coumarin-3-one reacts unusually undergoing dihydrofuran ring opening and the formation of the corresponding 3-(2-imino-1-(2-arylhydrazinyl)ethylidene)-chromane-2,4-diones.
The solvatochromic properties of the synthesized compounds were studied using electronic absorption spectra and quantum chemical
calculations. 相似文献
2.
N. A. Kondratova O. N. Kazheva G. G. Aleksandrov A. N. Chekhlov O. A. D��yachenko V. F. Traven 《Russian Chemical Bulletin》2011,60(9):1906-1916
2,3-Dihydrofuro[3,2-c]coumarin-3-one was synthesized in quantitative yield from 3-(??-bromoacetyl)-4-hydroxycoumarin in the presence of nucleophiles (including solvents). This compound undergoes keto-enol tautomerization and easily reacts with aromatic and heteroaromatic aldehydes to form crotonization products having a Z configuration and exhibiting strong fluorescence. 相似文献
3.
Reflux of equimolecular amounts 2-aminobenzylamine and isatins in acetic acid produced indolo[3,2-c]quinolin-6-ones in good yields. A proposed mechanism involving initial formation of a spiro compound is given. This isolable intermediate subsequently rearranges via a sequential isocyanate ring opening and a cyclisation process to a urea derivative which finally cyclized to the indolo[3,2-c]quinolin-6-ones. The urea derivative could be prepared separately and cyclized selectively to indolo[3,2-c]quinolin-6-one. Reaction of N-acetylisatin with 2-aminobenzylamine at room temperature yielded the 1,4-benzodiazepinone 3-(2-acetamidophenyl)-1,5-dihydro-1,4-benzodiazepin-2-one whereas its isomer 2(2-acetamidophenyl)-4,5-dihydro-1,4-benzodiazepin-3-one was obtained from 2-(2-acetylaminophenyl)-N-(2-aminobenzyl)-2-oxoacetamide in acetic acid at room temperature.The previously unknown linear isomer of indolo[3,2-c]quinolin-6-one, i.e. indolo[2,3-b]quinolin-11-one, has been prepared by thermal (260°C) cyclization of methyl 2-phenylamino indole-3-carboxylate, which in turn was prepared in two steps from methyl indole-3-carboxylate. 相似文献
4.
Sobha P. Gorugantula 《Tetrahedron》2010,66(10):1800-4757
Palladium-catalyzed, carbon monoxide-mediated reductive N-heterocyclization of nitro-heteroaromatic compounds having an alkene adjacent to the nitro-group affords bicyclic pyrrolo-fused heteroaromatic molecules. This type of reaction was used to prepare the fused bicyclo[3.3.0] ring-system: thieno[3,2-b]pyrrole, thieno[2,3-b]pyrrole, furo[2,3-b]pyrrole, pyrrolo[3,2-d]thiazole, and pyrrolo[2,3-d]imidazole and the bicyclo[4.3.0] ring-systems: pyrrolo[3,2-b]pyridine, pyrrolo[2,3-b]pyridine, pyrrolo[3,2-c]pyridine, pyrrolo[2,3-c]pyridine, pyrrolo[3,2-c]pyridazine, and pyrrolo[3,2-d]pyrimidine in 32-94% yield. 相似文献
5.
I. A. Os’kina A. Ya. Tikhonov I. Yu. Bagryanskaya Yu. V. Gatilov O. S. Fedorova 《Russian Journal of Organic Chemistry》2013,49(10):1497-1501
The reaction of 4-hydroxycoumarin with 2-acetyloxiranes in dimethylformamide in the presence of triethylamine gave 2,3-dihydro-4H-furo[3,2-c]chromen-4-ones which were converted into 4H-furo[3,2-c]-chromen-4-one derivatives as a result of dehydration or fragmentation. 相似文献
6.
Aihua Zhou 《Tetrahedron letters》2005,46(12):2045-2048
Two-step cyclizations of 2-alkylthiazolines or 2-alkyloxazolines with α,α-disubstituted diacid chlorides produce excellent yields of 6,6-dialkyl-2,3-dihydrothiazolo[3,2-a]pyridine-5,7-diones and 6,6-dialkyl-2,3-dihydrooxazolo[3,2-a]pyridine-5,7-diones in refluxing acetonitrile containing Et3N. Similar cyclizations using N-(chlorocarbonyl) isocyanate in place of diacid chlorides produced 2,3-dihydrothiazolo[3,2-c]pyrimidine-5,7-diones or 2,3-dihydrooxazolo[3,2-c]pyrimidine-5,7-diones, respectively. Each cyclization proceeded through cyclic ketene-N,X-acetal (X = O or S) intermediates. 相似文献
7.
V. Yu. Mortikov L. A. Rodinovskaya A. E. Fedorov A. M. Shestopalov P. A. Belyakov 《Russian Chemical Bulletin》2014,63(2):443-456
Formylation of pyrazole and 2,5-dimethylpyrazole gave a number of pyrazole-containing aldehydes, which can be used to obtain chromenes, tetrahydrochromenes, 1,4-dihydropyrano[2,3-c]pyrazoles, pyrano[3,2-c]chromenes, thiochromeno[4,3-b]pyrans, pyrano[3,2-c]-quinolines, and thiazolo[3,2-a]pyridines. 相似文献
8.
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
9.
John W. Mcfarland William A. Essary Lale Cilenti William Cozart Philip E. Mcfarland 《Journal of heterocyclic chemistry》1975,12(4):705-707
Furo[3,2-c] pyridine (I) was nitrated to give 2-nitrofuro[3,2-c]pyridine (II). Bromination and chlorination of I gave, respectively, 2,3-dibromo-2,3-dihydrofuro[3,2-c]pyridine (III) and 2,3-dichloro-2,3-dihydrofuro[3,2-c]pyridine (IV). Oxidation of I with hydrogen peroxide afforded furo[3,2-c]pyridine 5-oxide (V) which was converted to I by phosphorus trichloride and to 4-chlorofuro[3,2-c]pyridine (VI) by phosphorus oxychloride. 相似文献
10.
V. Bobošík A. Krutošíková U. Jordis 《Monatshefte für Chemie / Chemical Monthly》1995,126(6-7):747-752
Summary A number of substituted 2,3-dimethylfuro[3,2-c]pyridines was synthesized. 3-(4,5-Dimethyl-2-furyl)propenoic acid (1) was converted to the acid azide2, which in turn was cyclized to give 2,3-dimethyl-5H-furo[3,2-c]pyridine-4-one (3) by heating at 240°C in Dowtherm. The pyridone3 was chlorinated with phosphorus oxychloride to give4, which was reduced with zinc and acetic acid to 2,3-dimethylfuro[3,2-c]pyridine (5). Treatment of4 with several secondary heterocyclic amines led to compounds6a–6c. Reaction of pyridone3 with phosphorus pentasulfide rendered the thione7, which was methylated to8a. The 4-methoxy derivative8b was obtained from4 with sodium methoxide. 2,3,5-Trimethylfuro[3,2-c]pyridine-4-one (9) was obtained by reaction of3 with methyl iodide.Dedicated to Professor Dr.Fritz Sauter on the occasion of his 65th birthday 相似文献
11.
E. G. Paronikyan Sh. Sh. Dashyan N. S. Minasyan G. M. Stepanyan 《Russian Journal of Organic Chemistry》2016,52(4):576-581
Ethyl 1-amino-8,8-dimethyl-5-(piperidin-1-yl)-8,9-dihydro-6H-pyrano[4,3-d]thieno[2,3-b]pyridine-2-carboxylate and ethyl 1-amino-5-(piperidin-1-yl)-6,7,8,9-tetrahydrothieno[2,3-c]isoquinoline-2-carboxylate reacted with benzoyl isothiocyanate to give the corresponding 1-thioureido derivatives which underwent cyclization to 2,2-dimethyl-5-(piperidin-1-yl)-10-thioxo-1,4,10,11-tetrahydro-2H-pyrano[4″,3″:4′,5′]pyrido-[3′,2′:4,5]thieno[3,2-d]pyrimidin-8(9H)-one and 5-(piperidin-1-yl)-10-thioxo-1,2,3,4,10,11-hexahydropyrimido-[4′,5′:4,5]thieno[2,3-c]isoquinolin-8(9H)-one. The cyclization products were converted into 8-chloro derivatives, and the chlorine atom therein was replaced by various amines. 相似文献
12.
Stephen Michael Rajesh Subbu Perumal J. Carlos Menéndez Sokkar Pandian Ramachandran Murugesan 《Tetrahedron》2012,68(27-28):5631-5636
An environmentally friendly approach to the diastereoselective synthesis of trans-4-oxo-3-aryl-3,4-dihydro-2H-furo[3,2-c]coumarin-2-carbonitriles, trans-2-benzoyl-3-(aryl)-2H-furo[3,2-c]chromen-4(3H)-ones and trans-ethyl-4-oxo-3-(aryl)-3,4-dihydro-2H-furo[3,2-c]chromene-2-carboxylates in good yields is described. The method is based on the sequential multicomponent reactions of 4-hydroxycoumarin, aromatic aldehydes and in situ generated cyanomethylpyridinium, phenacylpyridinium/(2-ethoxy-2-oxoethyl)pyridinium ylides, in the presence of the ionic liquid [BMIm]OH, which functions both as a catalyst and the reaction medium. 相似文献
13.
《Mendeleev Communications》2022,32(4):454-456
Novel 4-oxo-4H-furo[3,2-c]pyran-3-carboxylates and 4-oxo- 4H-furo[3,2-c]chromene-3-carboxylates were prepared from available alkyl 3-bromo-3-nitroacrylates and 4-hydroxy-6- methyl-2H-pyran-2-one or 4-hydroxycoumarin, respectively. Their structures were confirmed by NMR and X-ray data. 相似文献
14.
Mingchuang He Zhaohua Yan Wangyang Wang Fuyuan Zhu Sen Lin 《Tetrahedron letters》2018,59(41):3706-3712
A novel and efficient strategy for the synthesis of furo[3,2-c]coumarins has been developed via copper-catalyzed radical/radical cross-coupling of ketoxime carboxylates with 4-hydroxycoumarins. This redox-neutral reaction allows smooth and selective synthesis of 2-substituted, 3-substituted, 2,3-disubstituted and 2,3-fused polycyclic furo[3,2-c]coumarins. 相似文献
15.
Renata Studzińska Marcin WróblewskiAleksandra Karczmarska-Wódzka Renata Kołodziejska 《Tetrahedron letters》2014
2-Bromomethyl- and 2-iodomethyl-2,3-dihydrothiazolo[3,2-a]pyrimidin-5-ones are prepared via the reaction of 3-allyl-2-thiouracil derivatives with bromine or iodine chloride, respectively. The 6-bromo and 6-nitro derivatives are synthesized by an electrophilic substitution at C-6 of the thiazolopyrimidine system. As a result, novel 2,3-dihydrothiazolo[3,2-a]pyrimidin-5-one derivatives are obtained. Hydrogen halide elimination from the 2-halomethyl-2,3-dihydrothiazolo[3,2-a]pyrimidin-5-ones is also reported. 相似文献
16.
Z. G. Aliev O. P. Krasnykh A. N. Maslivets Yu. S. Andreichikov L. O. Atovmyan 《Russian Chemical Bulletin》1997,46(3):543-545
Thermal decarbonylation of 1-benzyl-4,5-dibenzoyl-2,3-dihydropyrrole-2,3-dione yields benzoyl[N-benzyl(phenylglyoxalimidoyl)]ketene. The latter undergoes intramolecular cyclization to 3-benzoyl-5-phenyl-2,3,4,5-tetrahydrofuro[3,2-c]isoquinolin-2-one. Which is oxidized to 3-benzoyl-5-phenyl-2H,4H-furo[3,2-c]isoquinolin-2-one under the reaction conditions. The crystal and molecular structure of the title compound was studied by
X-ray structural analysis.
Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 563–565, March, 1997. 相似文献
17.
2-Hydroxy-4H-benzo[4,5]thiazolo[3,2-a]pyrimidin-4-one 2a and 7-hydroxy-5H-thiazolo[3,2-a]pyrimidin-5-one 2b, were obtained in high yields under mild conditions from the cyclization reactions of bis-(2,4,6-trichlorophenyl) malonate and 2-aminobenzothiazole or 2-aminothiazole, respectively. A new class of compounds, 2,3-dihydro-4H-benzo[4,5]thiazolo[3,2-a]furo[2,3-d]pyrimidin-4-ones and 6,7-dihydro-5H-furo[2,3-d]thiazolo[3,2-a]pyrimidin-5-ones, were synthesized via the microwave assisted radical addition of compounds 2a and 2b to various alkenes using manganese(III) acetate. A preliminary acetylcholine esterase (AchE) inhibition test of compound 4e showed excellent (92%) inhibitory potential, comparable with the standard drug Donapezil®. 相似文献
18.
Salo Gronowitz Curt Roos Elina Sandberg Sergio Clementi 《Journal of heterocyclic chemistry》1977,14(5):893-897
Deuteriodeprotonation of some substituted 4,5-borazarothieno[2,3-c]pyridines (I) and 7,6-borazarothieno[3,2-c]pyridines (II) has been studied by the nmr technique. Exchange occurred predominantly in the 3-position, and the effect of methyl substitution on rate is discussed. The rates of exchange in some derivatives of I and II were compared with those of the isoelectronic thieno[2,3-c]pyridines (III) and thieno[3,2-c]pyridines (IV). Similar rates were obtained, confirming the aromatic nature of I and II. The deuteriodeprotonation of 4-methyl-4,5-borazaro-thieno[2,3-c]pyridine (Ie), 7-methyl-7,6-borazarothieno[3,2-c]pyridine (IIe), 4-methylthieno-[2,3-c]pyridine (IIIe), and 7-methylthieno[3,2-c]pyridine (IVe) were measured at different concentrations of deuteriosulfuric acid and different temperatures, showing that the protonated heterocycles are substrates in the deuteriodeprotonation reaction. Standard rates at p0 H and 100° were calculated for these systems. 相似文献
19.
Bruno Delest Jean-Michel Robert Marie-Renée Nourrisson Muriel Duflos Pierre Renard 《Tetrahedron》2004,60(29):6079-6083
The synthesis of a novel tetracyclic structure, 8,9-dihydroimidazo[4,5-c]pyrrolo[3,2-g]quinolin-4(5H)-one, has been achieved by a convergent pathway. Coupling of the weakly nucleophilic hindered aromatic amine with 1-benzylimidazole-4-carboxylic acid, 7, afforded the corresponding amide 9 using a DCP/DMF complex; subsequent Heck-type arylation leading to desired tetracyclic molecule imidazo[4,5-c]-pyrrolo[3,2-g]quinolin-4(5H)-one. 相似文献
20.
Maksym A. Kryuchkov Roman I. Zubatyuk Igor F. Perepichka Oleg V. Shishkin Sergei V. Tolkunov 《Monatshefte für Chemie / Chemical Monthly》2010,26(9):35-43