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1.
The 13C NMR spectra of [1.2]-spirenes 2 and spiro[2.4]hepta-(4.6)-dienes 5 are described and the effects of substituents are discussed. A bonding model of the [1.2]-spirenes 2 is derived on the basis of C-H coupling constants and calculated charge densities. The 13C NMR shifts of 1-aryl-spiro[2.4]hepta-(4.6)-dienes 6 show a good correlation with the Hammett σp constants of the substituents in p-position of the phenyl ring. Conclusions on spiroconjugation in [1.2]-spirenes 2 are drawn from comparing the 13C shifts of similar substituted [1.2]-spirenes and spiro[2.4]hepta-(4.6)-dienes. The spiroconjugation in [1.2]-, [2.2]- and [2.3]-spirenes 2, 3 and 4 is discussed comparing the calculated charge densities with the δ (13C) values, as well as the UV and p.e. spectra. 相似文献
2.
A new synthetic pathway to spiro[cyclohexane-1,3′-indoline]-2′,4-diones was found starting from 3-chloromethylene-2-indolones 1 and Danishefsky's diene 2. Their synthesis consists of several steps involving the formation of the cycloadducts, the 6-chloro-4-trimethylsilyloxy-2-methoxyspiro[cyclohex-3-en-1,3′-indolin]-2′-one derivatives, transformed into spiro[cyclohexa-2,5-dien-1,3′-indoline]-2′,4-diones via 6-chloro-spiro[cyclohex-2-en-1,3′-indoline]-2′,4-dione intermediates. The reduction of spiro[cyclohexa-2,5-dien-1,3′-indoline]-2′,4-diones gave spiro[cyclohexane-1,3′-indoline]-2′,4-diones 7. Using a ‘one pot reaction’, starting from 1 and 2, compounds 7 were obtained in satisfactory overall yield. 相似文献
3.
Yu. M. Atroshchenko I. E. Shakhkel'dyan O. Ya. Borbulevich A. N. Shchukin M. Yu. Antipin V. N. Khrustalev 《Russian Journal of Organic Chemistry》2005,41(11):1683-1689
Anionic hydride adduct of 1-(2-hydroxyethoxy)-2,4-dinitrobenzene was brought into a double Mannich condensation with formaldehyde and methylamine to furnish a mixture of isomeric 3-azabicyclo[3.3.1]nonanes: 3-methyl-6-(2-hydroxyethoxy)-1,5-dinitro-3-azabicyclo[3.3.1]non-6-ene and 3-methyl-6,6-ethylenedioxy-1,7-dinitro-3-azabicyclo[3.3.1]nonane. By means of NMR spectroscopy, X-ray difraction analysis, and quantum chemistry (PM3) we demonstrated that the spirocyclic isomer had chair-chair conformation with diequatorial orientation of substituents in positions 3 and 7. 相似文献
4.
Condensation of N-substituted 3-azabicyclo[3.3.1]nonan-9-ones with difunctional N,N-, N,S-, and N,O-centered nucleophiles (o-phenylenediamine, 1,2-diphenylethane-1,2-diamine, 2-aminobenzenethiol, cysteine, 2-aminophenol, serine) gave the corresponding spiro heterocyclic compounds fused at the C9 atom. Treatment of N-tert-butoxycarbonyl-substituted spiro compounds with anhydrous hydrogen chloride resulted in elimination of the tert-butoxycarbonyl group with formation of spiro[3-azabicyclo[3.3.1]nonane-9,2′-azole] hydrochlorides. 相似文献
5.
Ammar Mustafa N. M. Mikhailova N. S. Prostakov 《Chemistry of Heterocyclic Compounds》1996,32(1):65-67
9-Phenacylidene-4-azaf luorene and 9-bromo-9-(-bromophenacyl)-4-azafluorene have been used in the synthesis of spiro compounds with fragments of substituted pyrazolines. 1-Methyl-2-oxo-5 phenacylidene-indeno[2, 3-e]-1,2-dihydropyridine and hydrazine gave 1-methyl-2-oxo-3 phenylspiro[indeno(2, 3-e)-1,2-dihydropyridine-5,5-pyrazoline-2]. 相似文献
6.
Yu. V. Tomilov E. V. Shulishov G. P. Okonnishnikova O. M. Nefedov 《Russian Chemical Bulletin》1995,44(11):2105-2108
Polycyclic spiro(1-pyrazoline-3,1-cyclopropanes) were obtained in 32–70 % yields by the reaction of diazocyclopropane generatedin situ with 2-methyltricyclo[3.2.1.02,4]oct-6-ene, spiro[2,4]hepta-4,6-diene dimer, benzvalene, spiro[2,3]hex-1-ene, methyl 1-methylcyclopropene-3-carboxylate, buta-1,3-diene, and 2-methylbuta-1,3-diene.Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2199–2202, November, 1995.This study was financially supported by the Russian Foundation for Basic Research (Grant No. 94-03-08902). 相似文献
7.
G. G. Dyadyusha N. N. Romanov A. D. Kachkovskii A. I. Tolmachev 《Chemistry of Heterocyclic Compounds》1980,16(12):1221-1226
The -electron structure of thiazolopyridinium derivatives was analyzed thoroughly by the methods of quantum chemistry in order to ascertain the reason for the development of colors in the case of mesoionic compounds.See [1] for communication 4.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1618–1623, December, 1980. 相似文献
8.
S. M. Aldoshin L. O. Atovmyan O. A. Kozina V. A. Lokshin V. I. Minkin 《Russian Chemical Bulletin》1988,37(7):1385-1387
Conclusions We have carried out an x-ray diffraction study of tetramethylenespiro[1,3-dithiolane-2,7[7H]-furo[3,2-f]-[2H -1]-benzopyran], containing the three heteroatoms S, S, O in the spiro group. The orbital n-* interactions virtually do not affect the bond lengths in the spiro group of the molecule; therefore the Cspiro-O bond, which is ruptured upon photoexcitation, remains unlengthened in the ground state. The differences in the lengths of the chemically equivalent Cspiro-S bonds are due to electrostatic repulsions of the unshared electron pairs of the heteroatoms S and O, which have different relative orientation.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 7, pp. 1567–1569, July, 1988. 相似文献
9.
A. A. Ponomarev I. A. Markushina L. V. Popova 《Chemistry of Heterocyclic Compounds》1967,3(3):325-329
Research on synthesis of polycyclic spirans of the 1, 6-dioxaspiro-[4, 4]nonane group is continued. Electrolysis of methanol solutions of 2-furylcyclopentanol, 2-(5-methyl-furfuryl)cyclopentanol, and 2-furfuryl-1-indanol, gives, by intramolecular alkoxylation, spiro{perhydrocyclopenta[b]furan-2, 2-(5dihydrofuran)}, spiro{perhydrocyclopenta[b]furan-2, 2-(5-methoxy-5-methyl-2, 5-dihydrofuran)}, and spiro{2, 3, 3a, 8b-tetrahydro-4H-indeno[1, 2-b]furan-2, 2-(5-methoxy-2, 5-dihydrofuran)}, hitherto undescribed in the literature. Depending on the conditions, catalytic hydrogenation of these gives: spiro{perhydiocyclopenta[b]furan-2, 2-(5-methoxytetrahydrofuran)}, spiro{2, 3a, 8b-tetrahydro-4H-indeno[1, 2-b]furan-2, 2-(5-methoxytetrahydrofuran)}, spiro{perhydrocyclopenta[b]furan-2, 2-tetrahydrofuran}, and spiro{2, 3, 3a, 8b-tetrahydro-4H-indeno[1, 2-b]furan-2, 2-tetrahydrofuran}.For Part XXXI see [1]. 相似文献
10.
Shashikanth Ponnala Devi Prasad Sahu Rishi Kumar Prakas R. Maulik 《Journal of heterocyclic chemistry》2006,43(6):1635-1640
11.
Renate Dworczak 《Monatshefte für Chemie / Chemical Monthly》1991,122(8-9):731-737
Summary The reactivity of cyanomethylene-indolones (1 a–e) and 2-(dicyanomethylene)-indan-1,3-dione (4) towards 1,5-disubstituted 3-pyrazolones (2 a–c) was investigated. The reactions yield spiro[indene- and spiro[indole-4- and 6-pyrano[2,3-c]pyrazoles] (3 a–e,5 a–c). The structures are proven by13C-NMR-spectroscopy. The mechanisms of the reactions are discussed. 相似文献
12.
Mustazza C Borioni A Sestili I Sbraccia M Rodomonte A Ferretti R Del Giudice MR 《Chemical & pharmaceutical bulletin》2006,54(5):611-622
Some spiro[piperidine-4,2'(1'H)-quinazolin]-4'(3'H)-ones 3 and spiro[piperidine-4,5'(6'H)-[1,2,4]triazolo[1,5-c]quinazolines] 4 were synthesized and evaluated as ligands of the nociceptin receptor. The examined compounds showed partial agonistic activity, except compounds 3, 4n that proved to be pure antagonists. 相似文献
13.
The arylidienes of fluorinated spiro thiazolidines (5) containing α,β-unsaturated function have been used as component of Micheal addition with equimolar amount of 2-aminopyridine (6a) to give novel fluorinated spiro [indole-3,2′-pyrido[1,2-a]thiazolo[5,4-e]pyrimidines] (7) in a single step under microwaves in presence of montmorillonite KSF as solid support. The new improved synthetic method for fluorinated spiro [indole-3,2′-thiazolo[4,5-d]pyrimidines] (8) has also been developed involving the reaction of (5) with thiourea under monomode microwave reactor. Comparison with conventional synthesis and multimode microwave oven indicated the enhanced yield with faster reactions under monomode microwave reactor. Structure-activity relationships between the chemical structures and the antimycobacterial, antifungal activity of the evaluated compounds are also discussed. 相似文献
14.
Vladimir Kouznetsov Alirio PalmaWilson Rozo Elena StashenkoAli Bahsas Juan Amaro-Luis 《Tetrahedron》2003,59(3):419-425
The transformation of N-substituted 3,4-dihydrospiro[quinoline-2,1′-cyclohexanes] 2 and 3 has been examined in strong acid media, at elevated temperature. It was demonstrated that the N-(γ-cyanopropyl) spirodihydroquinolines 2 in the presence of concentrated sulfuric acid or PPA underwent hydrolysis affording the γ-aminoacids 3. The spirodihydroquinoline ring rearrangement readily produces 4-(2-oxopyrrolidinyl-1)spiro[indane-1,1′-cyclohexanes] 5 in good yields. The structures of all synthesized compounds were established by means of homonuclear and inverse-detected 2D NMR experiments. 相似文献
15.
The ability of methylenecyclopropane to undergo [2+2+1]-cycloaddition reactions with dicobalt-hexacarbonyl complexes of alkynes with formation of spiro[2,4]-heptenone derivatives has been revealed for the first time. The conditions for carrying out this reaction on the surface of adsorbents and zeolites have been established, so that it can be considered as a general preparative method for the preparation of various derivatives of spiro[2,4]heptenones (yields up to 80%). With monosubstituted acetylenes, the [2+2+1]-cycloaddition proceeds regioselectively, giving preferentially cyclopentenones containing a spiro fragment in the -position to the carbonyl. In the case of disubstituted acetylenes, -isomers are formed exclusively.For previous communication; see [1].Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 9, pp. 2061–2068, September, 1989. 相似文献
16.
Mohamed I. Hegab Adel S. Girgis I. S. Ahmed‐Farag 《Journal of heterocyclic chemistry》2006,43(5):1237-1242
17.
《中国化学快报》2016,(11)
Macleayine(1),a new natural occurring alkaloid with a unique spiro[furanone-piperidinedione]framework,was isolated from the aerial parts of Madeaya cordata.Its unusual structure was established by extensive spectroscopic analyses,computer-assisted structure elucidation software(ACD/Structure Elucidator),quantum chemistry calculations and ECD calculation.The result of virtual molecular docking predicted the compound can enhance the effects of insulin,and may be used to treat type II diabetes. 相似文献
18.
Chun-Mei Sai Ning-Bo Qin Cui-Cui Jia Da-Hong Li Kai-Bo Wang Yue-Hu Pei Jiao Bai Zhan-Lin Li Hui-Ming Hua 《中国化学快报》2016,27(11):1717-1720
Macleayine (1),a new natural occurring alkaloid with a unique spiro[furanone-piperidinedione] framework,was isolated from the aerial parts of Macleaya cordata.Its unusual structure was established by extensive spectroscopic analyses,computer-assisted structure elucidation software (ACD/Structure Elucidator),quantum chemistry calculations and ECD calculation.The result of virtual molecular docking predicted the compound can enhance the effects of insulin,and may be used to treat type II diabetes. 相似文献
19.
《Tetrahedron: Asymmetry》2007,18(19):2365-2376
Stereoselective [3+2] cycloadditions of trimethylenemethane (TMM) to the exocyclic CO and CN double bonds of (1S,3EZ,4R)-3-arylimino-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ones gave the corresponding spiro[bicyclo[2.2.1]heptane-2,2′-furan] and spiro[bicyclo[2.2.1]heptane-3,2′-pyrrolidine] derivatives. Further stereoselective reductions of the CN or CO bond in these cycloadducts furnished new chiral amines, diamines, and a new aminoalcohol. All cycloadditions and reductions of the CN double bonds took place from the less hindered endo-face of the (1S,3EZ,4R)-3-arylimino-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ones, exclusively, thus giving the corresponding products in 100% de. The structures were determined by NMR, NOESY spectroscopy, and by X-ray diffraction. 相似文献
20.
S. N. Sirakanyan V. G. Kartsev E. K. Hakobyan A. A. Hovakimyan 《Russian Journal of Organic Chemistry》2018,54(6):923-928
Methods have been developed for the synthesis of new 8-amino-3-benzyl-5-(morpholin-4-yl)-1,2,3,4-tetrahydropyrimido[4′,5′: 4,5]thieno[2,3-c][2,7]naphthyridine starting from 7-benzyl-3-chloro-1-(morpholin-4-yl)-5,6,7,8-tetrahydro-2,7-naphthyridine-4-carbonitrile. 8-Hydrazinyl-3-benzyl-5-(morpholin-4-yl)-1,2,3,4-tetrahydropyrimido[4′,5′: 4,5]thieno[2,3-c][2,7]naphthyridine has been converted to isomeric pentacyclic structures with a triazole ring fused through the [c] side of the pyrimidine ring, and their Dimroth rearrangement has been accomplished in both acidic and basic media. New heterocyclic systems containing pyrrolo[1,2-a]pyrimidinone and pyrimido[1,2-a]azepinone fragments were obtained on the basis of the thieno-[2,3-c][2,7]naphthyridine derivative. 相似文献