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1.
Ivana Ozimec Landek Dijana Pešić Mladen Merćep Barbara Stanić Milan Mesić 《Journal of heterocyclic chemistry》2011,48(4):856-863
Synthesis of a novel class of fused heterotetracyclic compounds, 8H‐1‐thia‐8‐aza‐dibenzo[e,h]azulenes ( VII ), is described. Starting N‐benzoyl‐protected 5H‐dibenzo[b,f]azepine ( XI , PG = Bz) was oxidized to 5‐benzoyl‐10,11‐epoxy‐10,11‐dihydro‐5H‐dibenzo[b,f]azepine ( 2 ), which subsequently rearranged in Lewis acid‐induced epoxide ring opening to give 5‐benzoyl‐5,11‐dihydro‐10H‐dibenzo[b,f]azepin‐10‐one ( 3 ). Vilsmeier reaction of 3 provided β‐chlorovinyl aldehyde 4 that readily cyclized with ethyl 2‐mercaptoacetate to form dibenzazepino[4,5]‐fused thiophene structure 5 . Further transformation of substituent at C‐2 position of 5 and N‐deprotection led to final aminoalkoxy derivatives 9 . All compounds with tetracyclic skeleton were tested in vitro for their anti‐inflammatory activity. J. Heterocyclic Chem., (2011). 相似文献
2.
Photolysis reaction of dibenzo[a,d]cycloheptene dimer 3 provides three dibenzo[a,d]cycloheptyl dimers 4 , 5 and 6 under different irradiation conditions via the intramolecular degradative cyclodimerization. A tetracyclic benzo[4,5]cyclohepta[1,2,3‐de]naphthalene core is also synthesized. 相似文献
3.
《化学:亚洲杂志》2017,12(6):638-642
Developing new organic conjugated materials for high density memory devices is highly desirable. In this research, a novel donor–acceptor‐type twelve‐ring fused twistheteroacene, 2,7,19,24‐tetra‐tert ‐butyl‐13,30‐didodecyl‐9,17,26,34‐tetraphenyl benzo[8′,9′]triphenyleno[2′,3′:7,8]dibenzo[b,e][1,4]dioxino[1,2,3,4‐lmn]dibenzo[6′,7′:10′,11′]tetraceno[2′,3′:5,6][1,4]dioxino[2,3‐f][3,8]phenanthroline‐12,14,29,31(13H ,30H )‐tetraone ( DPyN ) has been synthesized and characterized. It displays high thermal stability, possesses a broad absorption band centered at 510 and 538 nm, and emits red fluorescence in organic solvents. A solution‐processed memory device with DPyN as an active element shows an excellent memory performance with an ON/OFF current ratio of 103.46:1 and a threshold voltage of −2.44 V. 相似文献
4.
William Clegg Ross W. Harrington Lauren G. Mercier Warren E. Piers 《Acta Crystallographica. Section C, Structural Chemistry》2013,69(4):436-438
The molecule of the title silepine compound, C28H24Si, lies on a crystallographic general position but has almost exact mirror symmetry. The seven‐membered silepine ring has a boat conformation, with a fold angle of 99.99 (9)° between the C—C=C—C stern and the C—Si—C prow. The planes of the phenyl substituents are rotated by 32.23 (6) and 31.80 (7)° out of the planes of the respective fused benzene rings. Similar folded conformations are found for other dibenzo[b,f]silepines, while analogous dibenzo[b,f]borepines, in which the B atom can participate in conjugation, have a more flattened heterocyclic ring. 相似文献
5.
This review presents a survey of synthetic methods and reaction mechanism of the dibenzo[d,f][1,3] dioxepine derivatives. Furthermore, the influence of the substituent groups in 6,6′‐position of dibenzo[d,f][1,3] dioxepine on their conformation is explored. The functional dibenzo[d,f][1,3] dioxepine synthetically versatiles substrate, as they can be used for synthesis of a large variety of π‐conjugated oligomer and polymer containing heterocyclic compounds, such as dibromination dibenzo[d,f][1,3] dioxepine derivative as a raw material of synthesis for organic semiconductor polymers. The synthetic and fluorescent property of π‐conjugated polymers basic on dibenzo[d,f][1,3] dioxepine also is explored. J. Heterocyclic Chem., (2012). 相似文献
6.
N‐Nonaflyl‐benzotriazole 1a reacts with enamines 2 in tetrahydrofurane (THF) at room temperature to afford o‐nonafluorobutansulfonamido‐phenylazo‐enamines 3 in 74–81% yield. Compound 1a reacts with 1‐diethylaminobutadien 2f twice, affording pyridazine derivative 3f in 20% yield. Ringopening of N‐cyano‐benzotriazole 1b with pyrrolidinocyclohexene 2a affords, under cleavage of pyrrolidine 1,2,3,4‐tetrahydro‐dibenzo[4,5:e]imidazo[1,2‐b][1,2,4]triazine 4 in 43% yield. 相似文献
7.
A new linear benz[f]indole derivative 15 bearing two methoxyls in the fused naphthalene moiety was prepared as a potential chemotherapeutic agent. The anomalous behaviour of two trimethoxynaphthalene intermediates in parallel stages of the planned synthesis route is emphasized, and the corresponding mechanisms for these cyclizing reactions are proposed and discussed. 相似文献
8.
Dijana Pei Ivana Ozimec Landek Renata Rup
i Marina Modri Iva Dapo Rudolf Trojko Mladen Merep Milan Mesi 《Journal of heterocyclic chemistry》2012,49(2):243-252
The present review focuses on dibenzo[b,f]oxepin‐10(11H)‐one ( I , X = O) and dibenzo[b,f]thiepin‐10(11H)‐one ( I , X = S) as common synthons in the efficient synthesis of various dibenzoxepino[4,5‐ and dibenzothiepino[4,5]‐fused five‐membered heterocycles: [2,3] fused thiophene ( II ), [3,4] fused thiophene ( III ), furan ( IV ), pyrrole ( V ), imidazole ( VI ), pyrazole ( VII ), oxazole ( VIII ), and thiazole ( IX ). The potential of I to be converted into reactive intermediates that readily undergo heteroaromatic annulation reactions by cyclocondensation with proper binucleophiles allows formation of a range of enumerated functionalized dibenzo[e,h]azulene [4] structures ( II , III , IV , V , VI , VII , VIII , IX ). Dibenzo[e,h]azulenes as heterotetracyclic scaffold can be exploited in further modifications to obtain compounds with altered physicochemical and biological profile. J. Heterocyclic Chem., (2012). 相似文献
9.
Dr. Robert Thoran Tristan Schuh Philipp Holling Dr. Florian Puls Dr. Olga Kataeva Prof. Dr. Hans-Joachim Knölker 《European journal of organic chemistry》2023,26(35):e202300591
The iron-catalyzed oxidative C−C homocoupling of diarylamines affords 2,2′-bis(arylamino)-1,1′-biaryls which represent crucial synthetic building blocks for an access to a range of seven-membered heterocyclic ring systems. Reaction with paraformaldehyde, diphenyl carbonate, and diphenyl sulfite as efficient 1,1-dielectrophiles led to dibenzo[d,f][1,3]diazepines, dibenzo[d,f][1,3]diazepinones, and dibenzo[c,e][1,2,7]thiadiazepine 6-oxides. The synthetic procedures enable short and practical routes to these 1,3-diazepine derivatives under mild reaction conditions and with a high tolerance of various functional groups. 相似文献
10.
Haruyasu Asahara Takuya Koizumi Eiko Mochizuki Takumi Oshima 《Acta Crystallographica. Section C, Structural Chemistry》2006,62(3):o136-o138
The crystal structures of the two thermally equilibrated conformational isomers of the epoxide 1′,5′‐dimethylspiro[10,11‐dihydro‐5H‐dibenzo[a,d]cycloheptene‐5,8′‐4′‐oxatricyclo[5.1.0.03,5]octane]‐2′,6′‐dione, C23H20O3, have been determined by X‐ray diffraction. In the tricyclic dione skeleton, the oxirane and cyclopropane rings adopt an anti structure with respect to the conjunct quinone frame. The spiro‐linked 10,11‐dihydro‐5H‐dibenzo[a,d]cycloheptene ring of the major isomer has a fairly twisted boat form, folding opposite to the adjoining cyclopropane methyl substituent, whereas the seven‐membered ring of the minor isomer has an almost ideal twist–boat form, inversely folding to the side of the relevant methyl group. The conformational structures of these isomers have been compared with those of the corresponding isomers of the unepoxidized homobenzoquinone. 相似文献
11.
Microwave‐Assisted Synthesis of Substituted Dibenzo[b,f][1,4]thiazepines,Dibenzo[b,f][1,4]oxazepines,Benzothiazoles, and Benzimidazoles
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A highly efficient synthesis for possessing 7‐membered rings with two heteroatoms is described, using efficient microwave‐assisted one‐pot method to synthesize (substituted) dibenzo[b,f][1,4]thiazepines [1] and dibenzo[b,f][1,4]oxazepines [2] in high yields (up to 99%) by cyclocondensations of o‐aminothiophenol or o‐aminophenol with o‐halobenzaldehydes, o‐fluoroacetophenone, and o‐fluorobenzophenone. In the absence of base, o‐aminothiophenol reacted with o‐halobenzaldehydes to afford benzothiazoles. 相似文献
12.
Eduardo Sobarzo‐Sánchez Eugenio Uriarte Lourdes Santana Ricardo A. Tapia Paulo Pérez Lourido 《Helvetica chimica acta》2010,93(7):1385-1394
2,3‐Dihydro‐6‐hydroxy‐5‐methoxy‐7H‐dibenzo[de,h]quinolin‐7‐one, 6‐hydroxy‐5‐methoxy‐7H‐dibenzo[de,h]quinolin‐7‐one, and 2‐(6,7‐dimethoxy‐3,4‐dihydroisoquinolin‐1‐yl)benzyl benzoate, easily available by a Bischler–Napieralski cyclization, were used as starting materials to afford 6‐oxoisoaporphine and 2,3‐dimethoxy‐5,6,8,12b‐tetrahydroisoindolo[1,2‐a]isoquinoline as the main products. However, the catalytic hydrogenation of the benzyl benzoate derivative afforded, under mild conditions, 1,2,3,4‐tetrahydro‐6,7‐dimethoxy‐1‐(2‐methylphenyl)isoquinoline. 相似文献
13.
Dijana Pešić Ivana Ozimec Landek Ana Čikoš Biserka Metelko Vesna Gabelica Barbara Stanić Mladen Merćep Milan Mesić 《Journal of heterocyclic chemistry》2007,44(5):1129-1133
14.
Sebastian Hahn Philipp Biegger Markus Bender Dr. Frank Rominger Prof. Uwe H. F. Bunz 《Chemistry (Weinheim an der Bergstrasse, Germany)》2016,22(3):869-873
Thermal condensation of 2,3‐diamino‐1,4‐(bistriisopropylsilylethynyl)benzene, ‐naphthalene,‐anthracene, and ‐benzothiadiazole substrates with 1,2‐naphthalenedione forms bent benzophenazine‐type heteroarenes in a one‐step reaction in good to excellent yields. The targets are investigated by UV/Vis spectroscopy, cyclic voltammetry, and single‐crystal X‐ray crystallography. The packing of the targets in the solid state follows either a herringbone or a brick wall motif. In the case of 8,13‐bis(triisopropylsilylethynyl)dibenzo[a,i]phenazine, polymorphs with either packing result. 相似文献
15.
Tatyana A. Stroganova Viktor M. Red'kin Vladimir K. Vasilin Gennady D. Krapivin 《Journal of heterocyclic chemistry》2013,50(4):854-858
New Mannich bases were synthesized through an interaction of fused pyrrolo[1,2‐a][1,4]diazepines with secondary amines and formaldehyde. The reaction appears to be regioselective, yielding the monosubstituted products bearing N,N‐dialkylaminomethyl group at position 2 of the pyrrolodiazepine moiety. 相似文献
16.
The benzo[a]heptalene formation from 4‐[(R‐sulfonyl)acetyl]heptalene‐5‐carboxylates 15 and 5‐[(R‐sulfonyl)acetyl]heptalene‐4‐carboxylates 16 (R=Ph or morpholino) in the presence of R′SO2CH2Li and BuLi has been investigated (Scheme 6). Only the sulfonyl moiety linked to the C?O group at C(4) of the heptalene skeleton is found at C(3) of the formed benzo[a]heptalene‐2,4‐diols 3 in accordance with the general mechanism of their formation (Scheme 3). Intermediates that might rearrange to corresponding 2‐sulfonylbenzo[a]heptalene‐1,3‐diols lose HO? under the reaction conditions to yield the corresponding cyclopenta[d]heptalenones of type 11 (Schemes 6 and 7). However, the presence of an additional Me group at C(α) of the lithioalkyl sulfones suppresses the loss of HO?, and 4‐methyl‐2‐sulfonylbenzo[a]heptalene‐1,3‐diols of type 4c have been isolated and characterized for the first time (Schemes 8 and 10). A number of X‐ray crystal‐structure analyses of starting materials and of the new benzo[a]heptalenes have been performed. Finally, benzo[a]heptalene 4c has been transformed into its 1,2,3‐trimethoxy derivative 23 , a benzo[a]heptalene with the colchicinoid substitution pattern at ring A (Scheme 11). 相似文献
17.
《Journal of heterocyclic chemistry》2017,54(1):749-752
2‐Formylphenylboronic acid condenses with salicyloyl and anthraniloyl hydrazines directly to generate dibenzo‐fused versions of [1,2,3]diazaborinino[3,2‐b ][1,3,2]oxazaborinine and [1,3,2]diazaborinino[1,2‐b ][1,2,3]diazaborinine, respectively, in excellent yields. These compounds, the first members of heretofore unknown planar polycyclic boron heterocycle ring systems, were characterized thoroughly by high‐field NMR spectroscopy, X‐ray crystallography, and other techniques. 相似文献
18.
Prasat Kittakoop Sombat Nopichai Nuntawan Thongon Panarat Charoenchai Yodhathai Thebtaranonth 《Helvetica chimica acta》2004,87(1):175-179
Two new antimycobacterial dibenzo[b,f]oxepins, bauhinoxepins A (=3,3,5‐trimethylbenzo[b]pyrano[g][1]benzoxepin‐6,11‐diol; 1 ) and B (=6‐methoxy‐7‐methyl‐2‐(3‐methylbut‐2‐enyl)dibenzo[b,f]oxepine‐1,8‐diol; 2 ), were isolated from the roots of Bauhinia saccocalyx, and their structures were elucidated by analysis of spectroscopic data. Bauhinoxepins A and B exhibited antimycobacterial activities with respective minimum‐inhibitory concentrations (MIC) of 6.25 and 12.5 μg/ml. They were inactive (at 20 μg/ml) against the malarial parasite, and also inactive (at 20 μg/ml) towards the Vero, KB, and BC cell lines. 相似文献
19.
S. Bindya Wing‐Tak Wong M. A. Ashok H. S. Yathirajan R. S. Rathore 《Acta Crystallographica. Section C, Structural Chemistry》2007,63(9):o546-o548
In the structure of the title salt [systematic name: 3‐(10,11‐dihydro‐5H‐dibenzo[a,d][7]annulen‐5‐ylidene)‐N,N‐dimethylpropan‐1‐aminium 2,4,6‐trinitrophenolate] of a tricyclic antidepressant, C20H24N+·C6H2N3O7−, the dimethylaminopropyl subunit possesses a classical static conformational disorder. The central cycloheptadiene ring adopts a bent conformation that is intermediate between boat and chair forms, leading to a butterfly shape for the hetero‐tricyclic moiety. In a complementary fashion, donors from amitriptyline and acceptors from picrate form intermolecular C—H...O hydrogen bonds and N—H...O salt bridges. These hydrogen bonds cluster amitriptyline and picrate ions into a closed R44(36) hetero‐tetramer, whereas intermolecular C—H...π interactions between amitriptyline ions cluster them into homo‐dimers. Significant π–π stacking interactions are also observed between aromatic rings of amitriptyline and picrate, and these, combined with the C—H...π interactions, associate molecules into linear arrays along the [11] direction. 相似文献
20.
Liang Li Hai‐Ying Ren Xiao‐Dong Yang Jing‐Feng Zhao Gan‐Peng Li Hong‐Bin Zhang 《Helvetica chimica acta》2004,87(11):2943-2947
From the stems of Schisandra rubriflora, two novel partially saturated dibenzocyclooctene lignans, named rubriflorin A ( 1 ) and B ( 6 ), as well as the seven known partially saturated dibenzocyclooctene lignans kadsumarin A ( 2 ), kadsurin ( 3 ), heteroclitin B ( 4 ), heteroclitin C ( 5 ), heteroclitin D ( 7 ), interiorin ( 8 ), and interiorin B ( 9 ) were isolated. The structures of the new compounds 1 and 6 were established on the basis of spectral analysis as (5R,6S,7R,8R,13aS)‐8‐(acetyloxy)‐5,6,7,8‐tetrahydro‐1,2,3,13‐tetramethoxy‐6,7‐dimethylbenz([3,4]cycloocta[1,2‐f][1,3]benzodioxol‐5‐yl (2Z)‐2‐methylbut‐2‐enoate and (6R,7R,12aS)‐7,8‐dihydro‐12‐hydroxy‐1,2,3,10,11‐pentamethoxy‐6,7‐dimethyl‐6H‐dibenzo[a,c]cycloocten‐5‐one, respectively. 相似文献