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1.
Tat'yana T Kucherenko Roman Gutsul Vladimir M Kisel Vladimir A Kovtunenko 《Tetrahedron》2004,60(1):211-217
Previously unknown 3-arylamino-1,2-dihydro-1-isoquinolones were obtained by condensation of 2-cyanomethylbenzoic acid with arylamines. Isonicotinoylation of the compounds was shown to proceed at the carbon atom in the 4-position to give 3-arylamino-4-isonicotinoyl-1,2-dihydro-1-isoquinolones which were quaternized with alkylating agents and formed the corresponding pyridinium salts. Deprotonation of the latter induced intramolecular conjugated addition with the pyrrole ring closure and formation of spiro compounds. The structure of the products was confirmed by NMR, IR and UV spectroscopy and by synthesis of the model compound, 3-(4-tolyl)-2,3,4,5-tetrahydro-1H-pyrrolo[2,3-c]isoquinoline-1,5-dione. 相似文献
2.
An efficient synthetic method for 1′-aryl-2′-(2-oxoindolin-3-yl)spiro[indoline-3,5′-pyrroline]-2,3′-diones was successfully developed via the one-pot domino reaction of arylamines, acetone, and isatins in acetic acid. The reaction mechanism involved the sequential Michael addition and ring closure of the in situ formed 3-N-aryliminoisatin and isatylidene acetone. 相似文献
3.
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
4.
Chiaki Kuroda Shigenobu Honda Yuki Nagura Hiroyuki Koshio Taku Shibue Tokio Takeshita 《Tetrahedron》2004,60(2):319-331
The two title carbon frameworks were synthesized utilizing a new type of iron-induced cyclization reaction of 2-(trimethylsilylmethyl)pentadienal. 2-Methylspiro[4.5]dec-2-en-1-one was obtained from (Z)- and (E)-4-cyclohexylidene-2-(trimethylsilylmethyl)but-2-enal. It was found that the (Z)-substrate isomerized to (E)-intermediate followed by cyclization to afford the initial product, 2-methylenespiro[4.5]dec-3-en-1-ol, which was isomerized to the above product. The cyclization of 4-(4-alkyl)cyclohexylidene-2-(trimethylsilylmethyl)but-2-enal proceeded stereoselectively. While, (E)-3-(cyclohex-1-en-1-yl)-2-(trimethylsilylmethyl)prop-2-en-1-al cyclized immediately affording 8-methylenebicyclo[4.3.0]non-9-en-7-ol. The corresponding (Z)-isomer gave several cyclization products as a complex mixture. 相似文献
5.
Reaction of bicyclo[4.2.0]octane-2,5-diones with trimethylsilyl iodide gave bicyclo[3.3.0]oct-1(5)-en-2-ones by a clean reductive rearrangement in good yields, providing a simple and effecient synthetic method for the enones. 相似文献
6.
Novel acridine spirocompounds, spiro[dihydroacridine-9′(10′H),5-imidazolidine]-2-thiones have been prepared by the spontaneous cyclization of 1-substituted 3-(acridin-9-ylmethyl)thioureas, which were obtained from 1-(acridin-9-yl)methanamine, N-(acridin-9-ylmethyl)propan-1-amine, and N-(acridin-9-ylmethyl)benzylamine and alkyl/aryl isothiocyanates, as continuation of our previous studies on new acridine spirocycles. Imidazolidine-2-thiones thus obtained were subsequently transformed with mesitylnitrile oxide to imidazolidine-2-one analogues, some of which partly reopened to the corresponding (acridin-9-ylmethyl)ureas. An unusual spirocyclization via a CH carbanion instead of the N-1 nitrogen has been found for 3-(acridin-9-ylmethyl)-1-(acridin-9-yl)thioureas possessing two acridine rings. Structural modifications in positions 1, 3, and 4 of the spiro ring together with 1H, 13C, and 15N NMR spectroscopy and X-ray crystallography have been employed to rationalize a general propensity of various 9-substituted acridines to undergo easy spirocyclization. 相似文献
7.
Thiomethylmercury chlorides 2 Hg(CH2SMe)Cl · HgCl2 and Hg(CH2SPh)Cl react with magnesium in thf to give the Grignard compounds Mg(CH2SR)Cl (R = Me ( 1 ), Ph ( 2 )) in nearly quantitative yields. From thf/n‐hexane solutions of 2 precipitate at –40 °C colorless crystals of the composition Mg(CH2SPh)Cl · 3.5 thf ( 2 ′). X‐ray structure determination revealed, that the unit cell contains separated molecules of [Mg(CH2SPh)2(thf)3] and [MgCl2(thf)4]. In the [Mg(CH2SPh)2(thf)3] molecules magnesium is distorted trigonal‐bipyramidally coordinate. Two PhSCH2 and one thf ligand occupy the equatorial positions and two further thf ligands the apical ones. In the [MgCl2(thf)4] molecules Mg displays an octahedral coordination with chloro ligands in mutual trans position. Temperature dependent NMR measurements of 2 reveal that in thf the Schlenk equilibrium operates; the composition of the equilibrium mixture at room temperature was estimated to be 89% Mg(CH2SPh)Cl and 11% Mg(CH2SPh)2. 相似文献
8.
T Suzuki H Inagaki H Hamajima H Uesaka K Hori T Ikami 《Chemical & pharmaceutical bulletin》1999,47(6):880-883
Three metabolites of N-[2-(1-azabicyclo[3.3.0]octan-5-yl)ethyl]-2-nitroaniline fumarate (SK-946), a novel central muscarinic cholinergic receptor agonist, were prepared to confirm their proposed structures, and tested for muscarinic receptor affinity in vitro. 相似文献
9.
Donn G. WishkaDaniel P. Walker 《Tetrahedron letters》2011,52(37):4713-4715
The novel bridged bicyclic morpholinethione (±)-6-oxa-3-azabicyclo[3.1.1]heptan-2-thione (9) has been prepared in six steps. This conformationally restricted morpholinethione was prepared stereoselectively using straightforward chemistry and inexpensive starting materials. The key oxetane ring was formed via an intramolecular alkylation reaction. 相似文献
10.
Massimo Gianotti Daniele AndreottiDavide Casotto Mario MattioliAnna Mingardi Francesca PavoneRoberto Profeta Filippo Valente 《Tetrahedron letters》2011,52(2):329-331
A new synthetic pathway to the final compound 1-[(1S)-5’,11’-dihydrospiro[cyclopentane-1,10’-dibenzo[a,d]cyclohepten]-3-yl]-3-azetidinecarboxylic acid (1) was set up. The two preparative chiral HPLC separations needed in the first route were successfully avoided and replaced by two diastereomeric crystallizations of intermediate compounds 5 and 10. 相似文献
11.
Raphael Bextermller Hartmut Redlich Klaus Schnieders Sven Thormhlen Roland Frhlich 《Angewandte Chemie (International ed. in English)》1998,37(18):2496-2500
As spiro sugars is an apt way of considering perhydroxylated 1,7-dioxaspiro[5.5]undecanes–a class of compounds which has not been found in nature up to now. The crystal structure of such a spiroacetal, in which the two pyran rings show the β-D -manno configuration, is depicted. Note that the all-trans arrangement of C-6, C,-5, Opyr, Cspiro, Opyr′, C-5′, and C-6′ does not allow any of the stereoelectronic effects that are typical of carbohydrates. 相似文献
12.
Several syn and anti atropisomers of 2-(5-benzo[b]fluorenyl)-2′-hydroxy-1,1′-binaphthyl and related compounds were synthesized from 1,1′-binaphthyl-2,2′-diol (BINOL). It was possible to separate the syn and anti atropisomers by silica gel column chromatography. The syn atropisomers are potential hetero-bidentate ligands for complex formation with metals. By starting from enantiomerically pure (R)-(+)-BINOL and (S)-(−)-BINOL, four optically active syn atropisomers and two anti atropisomers with high enantiomeric purity were obtained. The structures of two syn atropisomers and one anti atropisomer were established by X-ray structure analyses. 相似文献
13.
A BINOL-phosphoric acid-catalyzed furylogous Pinacol rearrangement is developed. This reaction produces spiro cyclopentanone in good yields under mild conditions. The enantioselective version of this reaction is also investigated using chiral phosphoric acid (CPA) as the catalyst. 相似文献
14.
A novel dicyanoheptafulvene 9 annulated by two spiro[4,5]deca-1,3-dienes was synthesized by the reaction of dispirocyclopentaazulenium cation 8 with bromomalononitrile. Although 9 was found to have a nonplanar heptafulvene structure by its X-ray crystallographic analysis, it is still capable of π-conjugation and thus shows appreciable contribution of the dipolar resonance form 9B based on its spectroscopic data. The degree of the contribution was further evaluated for various dicyanoheptafulvenes in terms of the partial sum of atomic charges of the dicyanomethylene group in the calculated structures besides the interplanar angles of the heptafulvene part and the length of the exocyclic double bond in the crystal structures. 相似文献
15.
Constantin Mamat 《Journal of organometallic chemistry》2004,689(10):1739-1745
1-(8-Methoxy-1-naphthyl)-1,2,2-tris(trimethylsilyl)silene (10) and the 1-[2,6-bis(alkoxymethyl)phenyl]-1,2,2-tris(trimethylsilyl)silenes (12a-d) were generated by the reaction of (dichloromethyl)tris(trimethylsilyl)silane (1) with two molar equivalents of 8-methoxy-1-naphthyllithium or 2,6-bis(alkoxymethyl)phenyllithium (8a-d), respectively, but proved to be unstable. 10 was trapped with excess of the applied naphthyllithium reagent to give 1,1-bis(8-methoxy-1-naphthyl)-1-[bis(trimethylsilyl)methyl]-2,2,2-trimethyldisilane (11); and 12a-d underwent spontaneous conversions and formed two types of substituted 2-oxa-1-silaindane derivatives (13a,b and 14b-d). Whereas silenes with an intramolecular amine coordination are thermally stable compounds which can be isolated, the intramolecular coordination of an ether group to the electrophilic silene silicon atom does not provide a comparable stabilization to the SiC system and the respective derivatives generated were converted into resultant products. 相似文献
16.
A new approach to helical primary structures of four-membered rings uses a cycloaddition of a trimethylenketeniminium salt to suitable tailored methylenecyclobutanes to assemble the desired carbon framework. The results are short and effective syntheses of (M)-trispiro[3.0.0.3.2.2]tridecane [(M)-5], and (P)- and (M)-tetraspiro[3.0.0.0.3.2.2.2]hexadecane [(P)- and (M)-24]. Unlike helices of three-membered rings, the specific rotation decreases, as the length of the helix increases. 相似文献
17.
1 INTRODUCTION Organic phosphine compounds always attract great interest for their unique properties and extensive uses in biochemistry, pesticide chemistry and synthetic organic chemistry. In the last two decades, much attention has been paid to phosphorus-containing olefin and acetylenic compounds for their applications in transition metal chemistry, asymmetric catalysis and photorearrang- ement [1~7 ]. Previously, we have reported the crystal structure of a novel host compound which … 相似文献
18.
D. A. Tikhomirov O. S. Slyadevskaya A. F. Mishnev A. V. Eremeev 《Chemistry of Heterocyclic Compounds》1991,27(12):1365-1367
The reaction of methyl bromopropiolate with diethanolmethylamine gave a quaternized 5-(methoxycarbonylmethyl)-4,6-dioxa-1-azabicyclo[3.3.0]octane, the structure and conformation of which were studied by x-ray diffraction analysis.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1695–1697, December, 1991. 相似文献
19.
利用2,3-丁二酮与丙二腈缩合形成双甲基双氰基环并内酰胺,经酸性水解得到双甲基环并内酯,然后和(S)-(-)-(1-苯基乙基)胺反应生成1,5-二甲基-2-(S)-(1′-苯基乙基)-2-氮杂-8-氧杂-双环[3.3.0]辛烷-3,7-二酮,通过元素分析、红外光谱、核磁共振氢谱和质谱对其结构进行了表征.用X射线单晶衍射法测定了目标产物的晶体结构,结果表明,晶体属单斜晶系,P21空间群,a=0.8777(18)nm,b=1.0102(2)nm,c=0.9009(18)nm,β=118.75(3)°,V=0.7003(2)nm3,Dc=1.296 g·cm-3,μ=0.089 mm-1,F(000)=292,Z=2,R1=0.0393,wR2=0.0955. 相似文献
20.
The novel functionalized ferrocene alkyne Ph2P(S)fcCCH (1; fc = ferrocene-1,1′-diyl) was synthesized from Ph2P(S)fcCHO (6) via the Corey-Fuchs reaction. It was further reacted with K2[HgI4]/KOH to give mercury(II) acetylide Hg{CCfcP(S)Ph2}2 (8), and with [Co2(CO)8] to afford the trimetallic Co2Fe complex [(μ-η2:η2-1){Co(CO)3}2](Co-Co) (9). All compounds were characterized by spectral methods (IR, NMR, and MS) and by combustion or high-resolution MS elemental analyses. In addition, the crystal structures of 1, Ph2PfcBr (5), 6, Ph2P(S)fcCHCBr2 (7), and 9 were determined by single-crystal X-ray diffraction. 相似文献