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1.
Summary Fringelite D was synthesized from 1,3,6,8-tetramethoxyanthracen-9-olvia two different efficient routes. The first one involved demethylation and subsequent dimerization. The other one started with dimerization to yield octamethylfringelite D and subsequent demethylation. The starting material was prepared in four steps from commercially available educts, the key step being a benzamideortho-lithiation. The spectroscopic properties of fringelite D were measured and are discussed. The dissociation, deprotonation, and protonation equilibria of fringelite D were characterized by their respectivepK values in ground and excited states and compared with those of hypericin. Homo- and heteroassociation properties of fringelite D were found to be similar to those of hypericin.
Synthese und Eigenschaften von Fringelit D (1,3,4,6,8,10,11,13-Octahydroxy-phenanthro[1,10,9,8,o,p,q,r,a]perylen-7,14-dion)
Zusammenfassung Fringelit D wurde auf zwei effizienten Routen aus 1,3,6,8-Tetramethoxyanthracen-9-ol synthetisiert. Die erste umfaßt Demethylierung und anschließende Dimerisierung. Die andere beginnt mit der Dimerisierung zu Octamethylfringelit D und endet mit einer Demethylierung. Das Ausgangsmaterial wurde in vier Stufen aus kommerziell zugänglichen Edukten dargestellt; der Schlüsselschritt ist eineortho-Lithiierung eines Benzamids. Die spektroskopischen Eigenschaften von Fringelit D wurden gemessen und werden diskutiert. Die Dissoziations-, Deprotonierungs- und Protonierungsgleichgewichte wurden durch ihrepK-Werte in Grundzustand und angeregtem Zustand charakterisiert und mit jenen des Hypericins verglichen. Die Homo- und Hetero-assoziationseigenschaften von Fringelit D sind jenen des Hypericins ähnlich.相似文献
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V. M. Kisil L. M. Potikha A. V. Turov V. A. Kovtunenko 《Chemistry of Heterocyclic Compounds》2008,44(2):214-224
The reaction of 7,12-dihydro-5H-isoquino[2,3-a]quinazolin-5-ones with o-xylidene dibromide leads to 11-oxo-4bH,5H,10H,11H,16H-10a-aza-15b-azoniadibenzo[a,e]pleiadene
bromides, which are converted to 11-oxo-10H,11H,16H-10a-aza-15b-azoniadibenzo[a,e]pleiadene salts upon oxidation using nitrobenzene.
The reaction of these salts with benzylamine leads to 6-{2-[(benzylimino)methyl]phenyl}-7,12-dihydroisoquino[3,2-b][2]benzazepin-14(6H)-ones,
which recyclize to 11-oxo-5H,10H,11H-10a-aza-15b-azoniadibenzo[a,e]pleiadene perchlorates upon the action of perchloric acid.
The reactions of the 10a,15b-diazadibenzo[a,e]pleiadene salts obtained with NaBH4 were studied and the structures of the reduction products were determined by spectral methods.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 280–292, February, 2008. 相似文献
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Data on the synthesis, reactions, crystal structure, and spectral characteristics of benzo[b]tellurophene, dibenzo[b,d]tellurophene, and their derivatives are reviewed and analyzed. 相似文献
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Reaction of 2-substituted 5-imino-7-oxo-1,3,4-thiadiazolo[3,2-a]pyrimidines with pentane-2,4-dione in polyphosphoric acid yields 9-oxo-1,3,4-thiadiazolo[3,2-a]pyrido[3,2-e]pyrimidines.Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 10, pp. 2037–2038, October, 1995.The authors are grateful to V. A. Dorokhov for the skilled preparation of the paper for publication. 相似文献
7.
Z. G. Aliev S. N. Shurov V. A. Glushkov L. N. Karpova Yu. S. Andreichikov L. O. Atovmyan 《Russian Chemical Bulletin》1997,46(10):1751-1754
The reaction of 5-phenyl-2,3-dihydrofuran-2,3-dione with 6,7-dimethoxy-3,4-dihydroisoquinoline gave 1-benzoyl-2-hydroxy-8,9-dimethoxy-3,5,6,10b-tetrahydropyrrolo[2,1-a]isoquinolin-3-one and its oxidation product,viz., 1-benzoyl-8,9-dimethoxy-2,3,5,6-tetrahydropyrrolo[2,1-a]isoquinoline-2,3-dione. The last-mentioned compound was studied by X-ray structural analysis.
Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 10, pp. 1845–1848, October, 1997. 相似文献
8.
V. I. Terenin E. A. Sumtsova S. Z. Vatsadze E. V. Kabanova I. F. Leshcheva A. P. Pleshkova N. V. Zyk 《Chemistry of Heterocyclic Compounds》2003,39(7):943-952
We have studied the behavior of asymmetrically substituted dipyrrolo[1,2-a;2',1'-c]pyrazines and their 5,6-dihydro analogs under phosphorylation reaction conditions. 相似文献
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S. G. Il'in M. V. Reshetnyak A. I. Yanovskii Yu. T. Struchkov O. Yu. Slabko G. A. Verbitskii V. A. Kaminskii 《Chemistry of Heterocyclic Compounds》2001,37(1):109-119
The spatial configurations of 7,9-diphenyl-5a,6-tetramethylene-5,5a,6,7-tetrahydropyrido[1,2-a]benzimidazole and 7,9-diphenyl-5a,6-tetramethylene-2,5a,6,7-tetrahydropyrido[1,2-a]benzimidazol-2-one have been established by X-ray crystallography. Analogous configurations are proposed for a series of other derivatives of 5,5a,6,7-tetrahydropyrido[1,2-a]benzimidazoles and some derivatives of 6,7-dihydro-5aH-pyrido[1,2-b]benzoxazoles on the basis of 1H NMR spectroscopic data and the results of quantum chemical calculations using the MNDO, AM1, and PM3 methods. 相似文献
10.
V. I. Terenin E. A. Sumtsova E. V. Kabanova A. P. Pleshkova N. V. Zyk 《Chemistry of Heterocyclic Compounds》2004,40(4):436-445
Esters, nitriles, and amides of dipyrrolo[1,2-a:2',1'-c]pyrazines have been synthesized by the acylation of dipyrrolo[1,2-a:2',1'-c]pyrazines and 5,6-dihydrodipyrrolo[1,2-a:2',1'-c]pyrazines with trichloroacetic acid chloride, p-tosyl isocyanate, and isocyanatophosphoric acid dichloride (Kirsanov isocyanate). 相似文献
11.
N. N. Polygalova A. G. Mikhailovskii E. V. Vikhareva M. I. Vakhrin 《Chemistry of Heterocyclic Compounds》2007,43(7):900-905
It has been shown that the Chichibabin reaction of enamines of the 1,2,3,4-tetrahydroisoquinoline series and 1,2,3,4-tetrahydrobenzo[f]isoquinoline
series with p-bromophenacyl bromide leads to pyrrolo[2,1-a]isoquinoline derivatives. The same heterocyclic system is obtained
on interaction of 1-alkyl-3,4-dihydroisoquinolines or their benzo[f]-analogs with oxalyl chloride. The obtained dioxopyrrolines
form derivatives of benzo[g]quinoxalino[2,3-b]indolizine on condensation with o-phenylenediamine.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 1068–1074, July, 2007. 相似文献
12.
V. I. Terenin E. A. Sumtsova M. A. Kovalkina S. Z. Vatsadze E. V. Kabanova A. P. Pleshkova N. V. Zyk 《Chemistry of Heterocyclic Compounds》2003,39(11):1487-1491
A series of previously unreported aldehydes has been prepared by the formylation reaction of dipyrrolo[1,2-a;2':,1'-c]pyrazines and their 5,6-dihydro analogs by DMF and phosphorus oxychloride. 相似文献
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A. E. Shchekotikhin Yu. N. Luzikov V. N. Buyanov M. N. Preobrazhenskaya 《Chemistry of Heterocyclic Compounds》2006,42(6):746-752
Nucleophilic substitution of methoxy groups in 4,11-dimethoxynaphtho[2,3-f]indole-5,10-dione by the action of primary and
secondary alkylamines, or arylamines leads to the formation of N-alkyl or N-aryl derivatives of 4,11-diaminonaphtho[2,3-f]indole-5,10-dione
respectively. 4,11-Diamino-1H-naphtho-[2,3-f]indole-5,10-dione is obtained by the dealkylation of 4,11-bis[(1-phenylethyl)amino]-1Hnaphtho[
2,3-f]indole-5,10-dione in the presence of a Lewis acid (BBr3).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 854–861, June, 2006. 相似文献
14.
Oxidative amination of 3-chloro-6,8-dimethylpyrimido[4,5-c]pyridazine-5,7(6H,8H)-dione with primary alkylamines and potassium amide in liquid ammonia gives rise to the corresponding 4-amino derivatives as the major products. The reactions with acyclic secondary amines are accompanied by annelation of the pyrrole moiety to the starting heterosystem to form 1-R-3-R"-6,8-dimethylpyrrolo[2",3";3,4]pyrimido[4,5-c]pyridazine-7,9(6H,8H)-diones. The reaction with piperidine as the aminating agent occurs exclusively as aminodehalogenation. The Sonogashira cross-coupling of 4-amino-3-chloro-6,8-dimethylpyrimido[4,5-c]pyridazine-5,7(6H,8H)-diones with terminal alkynes affords 1-R-2-R"-6,8-dimethylpyrrolo[3",2";3,4]pyrimido[4,5-c]pyridazine-7,9(6H,8H)-diones. 相似文献
15.
V. M. Polosin A. A. Astakhov M. A. Ryashentseva V. A. Tafeenko 《Russian Chemical Bulletin》1997,46(12):2121-2123
Skeletal isomerization of arylsilanes that occurs under conditions of catalytic dehydrocyclization and is accompanied by migration
of the triorganosilyl group was additionally confirmed by dehydrocyclization of dimethyl(2,4-dimethylphenyl)(1-naphthyl)silane
on chromium-containing oxide catalysts.
Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2236–2239, December, 1997. 相似文献
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A. Yu. Kovalevsky O. V. Shishkin I. A. Ronova I. I. Ponomarev S. V. Lindeman Yu. A. Volkova 《Russian Chemical Bulletin》1997,46(11):1866-1874
The X-ray study of 3,12-dichloro-5,14-diphenyl-7,9a,16,18a-tetrazadibenzo[a,l]pentacene-9,18-dione (1), a model compound for a novel class of thermostable polyheteroarylenes, polyquinoquinazolones, has been carried out. The
nonsymmetric flattened structure of the molecule observed is a result of intermolecular interactions. It was established using
quantum-chemical calculations by the semiempirical AM1 method that the annelation of the 1,6-dihydropyrimidinone ring by aromatic
cycles results in increasing the conformational flexibility of the dihydrocycle due to weakening the conjugation between the
carbonyl group and the remaining π-system of the molecule. It was shown by X-ray study and quantum-chemical calculations that
protonation of1 results in a substantial change in the molecular structure due to the large contribution of the 1,4-dihydro tautomeric form
to the structure of the 1,6-dihydropyrimidinone ring. A tendency for the conformational flexibility of the heterocycle to
increase upon protonation was revealed.
Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 1970–1978, November, 1997. 相似文献
18.
A. E. Shchekotikhin Yu. N. Lusikov V. N. Buyanov M. N. Preobrazhenskaya 《Chemistry of Heterocyclic Compounds》2007,43(4):439-444
Condensation of 2-formyl-or 2-cyano-3-chloro-1,4-dimethoxyanthraquinone with methyl thioglycolate in the presence of base
gave methyl 4,11-dimethoxyanthra[2,3-b]thiophene-5,10-dione-2-carboxylate and its 3-amino derivative respectively. Hydrolysis
of the ester group in methyl 4,11-dimethoxyanthra[2,3-b]thiophene-5,10-dione-2-carboxylate and subsequent decarboxylation
of the carboxylic acid formed gave 4,11-dimethoxyanthra[2,3-b]thiophene-5,10-dione. Condensation of 3-chloro-2-formyl-1,4-dimethoxyanthraquinone
with ammonia in the presence of sulfur gave 4,11-dimethoxyanthra[2,3-d]isothiazole-5,10-dione
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 538–543, April, 2007. 相似文献
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Condensation between 7-(1,1-dimethylethyl)-13-phenyl-8H-indeno[2,1-b]phenanthrene and paraformaldehyde produced the corresponding 9-fluorenylmethanol derivative, which on treatment with P2O5 to promote a Wagner-Meerwein rearrangement for ring expansion furnished 14-phenyldibenzo[a,j]anthracene in 88% yield. Similarly, 17,18-diphenyldibenzo[a,o]pentaphene possessing a helical twist and bearing two phenyl substituents at the most sterically congested C17 and C18 positions and other related compounds were likewise synthesized. Subsequent intramolecular arylation reactions involving the phenyl substituents produced polycyclic aromatic hydrocarbons with novel architectures. 相似文献