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1.
Paw-Wang Yang Jhy-An Chen Hidetsugu Wakabayashi Kimio Shindo Teruo Kurihara Chi-Phi Wu Masafumi Yasunami Tetsuo Nozoe 《中国化学会会志》1997,44(1):5-7
Variously functionalized 1,5- and 1,7-azulenequinones were easily derived in one-pot in 30-50% yield from the bromine-oxidation of 2-methoxyazulene and 2-methyl derivatives of 1-cyano-, 1-methoxycarbonyl- and its 7-isopropyl derivatives, while 1-methoxycarbonylazulene afforded several unstable products from which we could not isolate any azulenequinones. 1-Acetylazulene afforded 3-bromo-1,5- and -1,7-azulenequinones via side-chain brominated intermediates in high yield. 1,3-Dichloroazulene afforded a mixture of 3-chloro-1,5- and −1,7-azulenequinones, while 1-fluoro- and 1,3-diiodoazulene gave a mixture of 3-bromoazulenequinones. Analogous oxidation of 1,3-difluoroazulene produced 3-fluoroazulenequinones, but we could not isolate them due to its instability. Hydroxy group of 2-(3-hydroxypropyl)azulene was intact during this quinone formation reaction. 相似文献
2.
Hidetsugu Wakabayashi Akifumi Takano Kimio Shindo Masafumi Yasunami Jhy-An Chen Paw-Wang Yang Tetsuo Nozoe 《中国化学会会志》1996,43(4):301-304
Oxidation of 1-ethyl-, 1-propylazulenes, and their 5-isopropyl derivatives with bromine gave 3-bromo-1,5- and 3-bromo-l,7-azulenequinones (Type A) together with 3-bromo-l-hydroxy-5-isopropyl-l-alkylazulen-7-one and its isomeric products (Type B), while the same reaction of 1-methylazulenes afforded Type B products along with many unidentified products. On the other hand, 1-phenylazulene gave 3-phenyl-1,5- and 3-phenyl-l,7-azulenequinones (Type C) and Type B products in high yie]ds. 1,2-Polymethyleneazulenes afforded a considerable amount of 3-bromo-2-(ω-formylalkyl)azulenequinones together with Type B products. Possible pathways for the extrusion of the alkyl substituent at C-l are discussed. 相似文献
3.
Carey JS MacCormick S Stanway SJ Teerawutgulrag A Thomas EJ 《Organic & biomolecular chemistry》2011,9(10):3896-3919
Alk-2-enylstannanes with 4-, 5- and 6-alkoxy- or -hydroxy-substituents are transmetallated stereoselectively with tin(iv) halides to generate allyltin trihalides which react with aldehydes to give (Z)-alk-3-enols with useful levels of 1,5-, 1,6- and 1,7-stereocontrol. Alk-2-enylstannanes with a stereogenic centre bearing a hydroxy or alkoxy group at the 4-, 5- or 6-position, react with overall (Z)-1,5-, 1,6- and 1,7-syn-stereoselectivity with respect to the hydroxy and alkoxy substituents. The analogous reactions of alkoxy- and -hydroxyalk-2-enylstannanes with a methyl bearing stereogenic centre at the 4- or 5-position react with overall (Z)-1,5- and 1,6-anti-stereoselectivity with respect to the hydroxy and methyl substituents. 相似文献
4.
The reaction of (C5Me5RhCl2)2 with AgSbF6 in the presence of 1,5- and 1,7- dihydro-s-indacenes or 2,6-dimethyl-1,5- and 1,7-dihydro-s-indacenes provides stable η5- or η6-monorhodium complexes, respectively. A novel phane rhodium complex is described. 相似文献
5.
The synthesis of the novel 1,2-dihydroindolo [1,7-ab][1,5]benzodiazepine ring system 4 is described. Condensation of 2-fluoronitrobenzene with indoline provided the starting material for the synthesis, 1-(2-nitrophenyl)indoline (1a) in high yield. The nitro group was reduced catalytically and the resulting amino function was acylated to afford the heterocycle percursor amide 3. Refluxing this amide in phosphorus oxychloride brought about a Bischler-Napieralski type cyclodehydration to form the target 1,2-dihydroindolo[1,7-ab][1,5]benzodiazepine ring system. Dehydrogenation of the latter led to the fully aromatic indolo[1,7-ab][1,5]benzodiazepine structure 5, while reduction with sodium borohydride provided the 1,2,6,7-tetrahydroindolo[1,7-ab]-[1,5]benzodiazepine tetracycle 6. 相似文献
6.
By application of the Kress procedure for bromination it has been found that from the hydro-bromide of 1,7-naphthyridine with 1.1 equivalents of bromine in nitrobenzene a mixture of 3-and 5-bromo- and 3,5-dibromo-1,7-naphthyridine is obtained in reasonable yield. With an excess of bromine 3,5-dibromo-1,7-naphthyridine is nearly exclusively formed. Similar brominations of the hydrobromide of 1,8-naphthyridine with 1.1 equivalents of bromine gave 3-bromo- and 3,6-dibromo-1,8-naphthyridine. By using an excess of bromine a high-yield conversion into 3,6-dibromo-1,8-naphthyridine is observed. Bromination of the hydrochloride salt of 1,7- and 1,8-naphthyridine affords the same bromo derivatives. 相似文献
7.
Treatment of certain 1,5- and 1,7-diazaindenes with a small molar excess of hydrogen peroxide in acetic acid causes opening of the pyrrole ring with loss of the 2-C atom to give aminopyridyl ketones or aminopyridine carboxylic acids. The former have been used as intermediates in the synthesis of 3-substituted diazaindenes by reaction with dimethylsulphonium methylide. Stable iodine complexes with 1,5-diazaindenes may be formed: 6-(4-aminopyrid-3-yl)-6-oxohexanoic acid gave 4-(1-methyl-1,5-diazainden-3-yl)butanoic acid. 相似文献
8.
Johan Malm Bengt Rehn Anna-Britta Hrnfeldt Salo Gronowitz 《Journal of heterocyclic chemistry》1994,31(1):11-15
Through the use of Pd(0)-catalyzed coupling between 2- and 4-formyl-3-thiopheneboronic acid and 4-iodo-3-aminopyridine ( 1 ) and 3-bromo-2-aminopyridine, convenient one-pot procedures for the preparation of thieno[2,3-c]-1,7-naphthyridine ( 2 ), thieno[3,4-c]-1,7-naphthyridine ( 3 ), thieno[2,3-c]-1,8-naphthyridine ( 6 ) and thieno[3,4-c]-1,8-naphthyridine ( 7 ) have been developed. Thieno[3,2-c]-1,7-naphthyridine ( 4 ) and thieno[3,2-c]-1,8-naphthyridine ( 8 ) were obtained through the coupling of 2-tri-n-butylstannyl-3-thiophenaldehyde with 2,2-dimethyl-N-(4-iodo-3-pyridinyl)propanamide and 3-bromo-2-acetamidopyridine ( 1 ). The yield of 8 was further increased when copper(II) oxide was used as the co-reagent. The 13C nmr spectra of the six isomeric thieno[c]-fused 1,7- and 1,6-naphthyridines are discussed. 相似文献
9.
Ivar M. McDonald Robert Mate Alicia Ng Hyunsoo Park Richard E. Olson 《Tetrahedron letters》2018,59(8):751-754
Three novel tricyclic diamines (1,7-diazaisoadamantane, 1,5-diazaisoadamantane and 1,6-diazahomobrendane) were prepared. A flexible synthetic strategy was employed which used flat, aromatic azaindoles as the starting materials. The requisite azaindoles were prepared by a tandem Sonogashira coupling/intramolecular cyclization reaction. Ring saturation, appropriate functionalization and intramolecular alkylation provided the three novel tricyclic diamines cores. 相似文献
10.
The reaction of 3-bromo-4-phenyl-2,3-dihydro-1H-1,5-benzodiazepin-2-one with cyclic amines gives 3-aminoalkyl-4-phenyl-2,3-dihydro-1H-1,5-benzodiazepin-2-one. Thiazolo[4,5-b][1,5]benzodiazepine was isolated along with the substitution product when thiourea was used. 相似文献
11.
A new macrocyclic ligand, 1,3,5-triaza-2,4:7,8:16,17-tribenzo-9,12,15-trioxacyclooktadeca-1,5-dien (L) was synthesized by reaction of 2,6-diaminopyridine and 1,7-bis(2-formylphenyl)-1,4,7-trioxaheptane. Then, its Cu(II), Ni(II), Pb(II), Co(III) and La(III) complexes were synthesized by template effect by reaction of 2,6-diaminopyridine and 1,7-bis(2-formylphenyl)-1,4,7-trioxaheptane and Cu(NO3)2 · 3H2O, Ni(NO3)2 · 6H2O, Pb(NO3)2, Co(NO3)2 · 6H2O, La(NO3)3 · 6H2O, respectively. The ligand and its metal complexes have been characterized by elemental analysis, IR, 1H and 13C NMR, UV–Vis spectra, magnetic susceptibility, thermal gravimetric analysis, conductivity measurements, mass spectra and cyclic voltammetry. All complexes are diamagnetic and Cu(II) complex is binuclear. The Co(II) was oxidized to Co(III). The comparative electrochemical studies show that the nickel complex exhibited a quasi-reversible one-electron reduction process while copper and cobalt complexes gave irreversible reduction processes in DMSO solution. 相似文献
12.
A range of new 1,7-annulated indole derivatives has been prepared via a ring-closing metathesis approach starting from N-allyl-7-formyl indoles. 相似文献
13.
Weimin Zhang Fuqiang Ning Linda Váradi David E. Hibbs James A. Platts Miklós Nyerges Rosaleen J. Anderson Paul W. Groundwater 《Tetrahedron》2014
Substituents on the diene component have little influence on the periselectivity of the cyclizations of α,β:γ,δ-conjugated azomethine ylides, with 1,7-electrocyclizations predominating. In some cases, subtle changes to these substituents can, however, influence the product formed, through their effect on the relative energies of the transition states for the 1,5- (6π) and 1,7-electrocyclization (8π) processes. The most striking changes in periselectivity occur for phenylethenyl-substituted azomethine ylides 3d–f, which can give either a pyrroline 4d,f or dihydrobenzazepine 6e, depending upon the alkene configuration. 相似文献
14.
Chin-Ping Yang Jiun-Hung Lin 《Journal of polymer science. Part A, Polymer chemistry》1995,33(13):2183-2191
The novel diamine, 1,7-bis(4-aminophenoxy)naphthalene (1,7-BAPON), was synthesized and used to prepared polyimides. 1,7-BAPON was synthesized through the nucleophilic displacement of 1,7-dihydroxynaphthalene with p-fluoronitrobenzene in the presence of K2CO3 followed by catalytic-reduction. Polyimides were prepared from 1,7-BAPON and various aromatic tetracarboxylic dianhydrides by the usual two-step procedure that included ring-opening polyaddition to give poly(amic acid)s, followed by cyclodehydration to polyimides. The poly(amic acid)s had inherent viscosities of 0.74-2.48 dL/g. Most of the polyimides formed tough, creasible films. These polyimides had glass transition temperatures between 247–278°C and their 10% weight loss temperatures were recorded in the range of 515–575°C in nitrogen atmosphere. © 1995 John Wiley & Sons, Inc. 相似文献
15.
16.
Würthner F Stepanenko V Chen Z Saha-Möller CR Kocher N Stalke D 《The Journal of organic chemistry》2004,69(23):7933-7939
A detailed study on bromination and subsequent imidization of perylene bisanhydride with cyclohexylamine is reported. The present results reveal that previously reported 1,7-difunctionalized perylene bisimides are presumably contaminated with the respective 1,6 regioisomers. N,N'-Dicyclohexyl-1,7-dibromoperylene bisimide 1,7-3 is obtained for the first time in isomerically pure form, and its structure is unequivocally confirmed by X-ray analysis. By using regioisomerically pure 1,7-dibromoperylene bisimide 1,7-3, 1,7-dipyrrolidinylperylene bisimides 4a-c and 1,7-dipyrrolidinylperylene bisanhydride 5 as well as the unsymmetrically difunctionalized 1-bromo-7-pyrrolidinyl- and 1-cyano-7-pyrrolidinylperylene bisimides 7 and 8 are synthesized in good yield. 相似文献
17.
Of the three closo-carborane isomers (C2B10H12), closo-1,2-carborane has been used most widely in the synthesis of carboranyl amines. However, closo-1,2-carboranes are prone to deboronation to nido-7,8-carborane under various conditions including attack by basic amino groups. In order to overcome this problem, closo-1,7-carboranyl ethyl-, propyl-, and butylamine were synthesized, which should be more stable towards basic deboronation than their closo-1,2-carboranyl counterparts. These closo-1,7-carboranyl amines (5, 18 and 19) were synthesized using two different methods, both starting from the corresponding closo-1,7-carboranyl alkyl iodides (3, 14 and 15). One of the carboranyl alkyl amine (5) was conjugated with folic acid to form a closo-1,7-carborane-folic acid bioconjugate (20). 相似文献
18.
Fumitoshi Shibahara 《Tetrahedron》2009,65(26):5062-12876
The halogenation of 3-arylimidazo[1,5-a]pyridines was carried out with iodine, bromine, N-chlorosuccinimide, and 1-fluoro-2,4,6-trimethylpyridinium tetrafluoroborate as halogenating agents to give selectively halogenated products 1-halo-3-arylimidazo[1,5-a]pyridines in good to excellent yields. Kumada-Tamao-Corriu cross-coupling of the obtained 1-iodo-3-arylimidazo[1,5-a]pyridines and aryl Grignard reagents led to 1,3-diarylated imidazo[1,5-a]pyridines in good to excellent yields. Suzuki-Miyaura cross-coupling of the 1-bromo-3-phenylimidazo[1,5-a]pyridine and p- or m-methoxycarbonylphenylboronic acids furnished the coupling product in respective yields of 91% and 61%. The obtained 1,3-diarylated imidazo[1,5-a]pyridines showed a wide variety of fluorescent emissions in a wavelength range of 449-533 nm with improved quantum yields compared to monoarylated ones. 相似文献
19.
设计合成了三类含1,2,3-三氮唑结构的1,5-苯并硫氮杂[艹卓]化合物3-(1H-1,2,3-三氮唑)-4-芳基-2,5-二氢-1,5-苯并硫氮杂[艹卓](5a^5f)、3-(2H-1,2,3-三氮唑)-4-芳基-2,3-二氢-1,5-苯并硫氮杂[艹卓](6a^6f)和3-(1H-1,2,3-三氮唑)-4-芳基-2,3,4,5-四氢-1,5-苯并硫氮杂[艹卓](7a^7f).研究了中间体及目标产物的合成条件,分离出其中两个副产物并进行了结构确定.目标产物的抑真菌活性测试表明,化合物5a^5f对真菌具有良好的抑制作用,对新生隐球菌的抑制效果尤为突出.初步抑真菌构效关系研究表明, 1H-1,2,3-三氮唑环和C=C双键是化合物5a^5f抑真菌活性的关键官能团. 相似文献