Zur Chemie des 4-Hydroxy-cumarins

Ziegler, E.; Roßmann, U.; Litvan, F.

doi:10.1007/bf00901343

Cited by 11 publications

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“…It possesses the biologically interesting combination of an indole and a 2‐pyridone structure. Moreover, some derivatives have found interest in pharmacological investigations [4]. Recently, we published the synthesis and reactions of pyrido[3,2,1‐ jk ]carbazol‐6‐ones C with two aromatic rings [5].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and reactions of 4‐hydroxy‐8,9,10,11‐ tetrahydropyrido[3,2,1‐jk]carbazol‐6‐ones

Stadlbauer¹,

Dang²,

Berger³

2010

Journal of Heterocyclic Chem

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in Wiley InterScience (www.interscience.wiley.com).Tetrahydrocarbazoles 4 obtained from phenylhydrazines and cyclohexanones gave by cyclocondensation with 2-substituted malonates 5 in all cases 4-hydroxy-8,9,10,11-tetrahydropyrido[3,2,1-jk]carbazol-6-ones 6 by attack at the nitrogen and the aromatic ring of tetrahydrocarbazoles 4; the direction of the cyclization was not dependent on substituents either in the aromatic or the saturated ring; isomeric pyridocarbazoles could not be isolated. Electrophilic substitutions of pyridocarbazoles 6 under mild conditions took place exclusively at the 5-position and gave pyridocarbazolediones 9-11 with 5nitro-, 5-hydroxy or 5-chloro-substituents. Exchange of the chloro substituent in 11 gave 5-azido-and 5-amino products 12, 14 or 16. Reactions at the aromatic ring were not observed. Chlorination of 4hydroxypyridocarbazoles 6 with phosphoryl chloride by nucleophilic substitution took place exclusively at the 4-position and gave 4-chloropyridocarbazolones 17, which were further reacted to azides and amines 18, 19.

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Section: Introductionmentioning

confidence: 99%

Synthesis and reactions of 4‐hydroxy‐8,9,10,11‐ tetrahydropyrido[3,2,1‐jk]carbazol‐6‐ones

Stadlbauer¹,

Dang²,

Berger³

2010

Journal of Heterocyclic Chem

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“…Hard and borderline nucleophiles exclusively substituted chlorine in position 4, while soft nucleophiles substituted the group in position 3. Chromene-2-one derivatives have been reported for anticoagulant [3][4][5] , antibacterial [6][7] , antiinflamatory 8 , antimicrobial 9 , antiHIV [10][11][12][13] , antioxidant 14 , anticancer 15 and antiproliferative and antiviral 16 activities. It was found that when one biodynamic heterocyclic system was coupled with another heterocyclic system, enhanced biological activity was produced.…”

Section: Introductionmentioning

confidence: 99%

“…These newly synthesized polycyclic compounds (5)(6)(7)(8), have similar structure with lots of chromene-2-one compounds that are well known for their physiological activity [17][18][19] . From all chromene-2-ones, 4-hydroxychromene-2-one differs for its chemical reactivity, as it contains the enolysed β-ketoesteryc system.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Microbiological Activity of Some Newly Synthesized Derivatives of 2‐Oxo‐2H‐chromen‐2‐one

Daci-Ajvazi¹,

Govori²,

Omeragiq³

2010

Journal of Chemistry

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By the action of 2-amino-5-methylthio-1,3,4-thiadiazole, 3-amino-5-methylisoxazole, 2-amino-6-fluorobenzothiazole, 2-amino-5-chloropyridine, respectively, on 4-chloro-2-oxo-2H-chromene-3-sulfonyl chloride, the corresponding 9-methylthio-7,7-dioxo-7,7a-dihydro-5-oxo-7λ6,10-dithia-8,11-diaza-cyclopenta[b] phenantren-6-one, 9-methyl-7,7-dioxo-7H-5,8-dioxa-7λ6-thia-7a,11-diaza-cyclopenta[b] phenantren-6-one, 9-fluoro-7,7-dioxo-7H-5-oxa-7λ6,12-dithia-7a,13-diaza-indeno[1,2-b] phenantren-6-one and 9-Chloro-7,7-dioxo-7H-5-oxa-7λ6-thia-7a,12-diaza-benzo[α]anthracen -6-one were formed and they have been isolated in satisfying yields. Based on the biological activity of chromene-2-ones and heterocyclic compounds condensed in position 3 and 4, we also studied microbiological activity of these new compounds(5-8), againstStaphylococcus aureusATCC 25923,Streptococcus pneumoniae, Aeromonas Salmonicida, Bacillus sppand some of them exhibited significant activity.

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“…It possesses the biologically interesting combination of indole and 2-pyridone structures. Moreover, some derivatives have found interest in pharmacological [5] or in dye chemistry [6]. Our interest is focused to 4-hydroxy-5-substituted pyrido[3,2,1-jk]carbazol-6-ones (4, 5) which possess 2 reactive positions: the hydroxy group at C-4, which can be substituted by various nucleophiles, and the CH-acidic proton at C-5, which reacts with a large number of electrophiles.…”

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confidence: 99%

“…4-Hydroxy-5-phenylpyrido [3,2,1-jk]carbazol-6-ones (4,5), which were obtained from carbazoles 1 and malonates 2 or 3, were converted to reactive intermediates such as 4-chlorides 9 or 4-tosylates 10, which gave in turn 4-azido-5-phenyl derivatives 11. 5-Alkyl-4-azides 11 were not obtained in this manner; however a new one-pot azidation reaction was developed starting from 4-hydroxy derivatives 4 which gave azides 11 in good yields.…”

mentioning

confidence: 99%

Synthesis and ring closure reactions of pyrido[3,2,1-jk]carbazol-6-ones

Dang

Knobloch

Habib

et al. 2005

Journal of Heterocyclic Chemistry

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4-Hydroxy-5-phenylpyrido[3,2,1-jk]carbazol-6-ones (4, 5), which were obtained from carbazoles 1 and malonates 2 or 3, were converted to reactive intermediates such as 4-chlorides 9 or 4-tosylates 10, which gave in turn 4-azido-5-phenyl derivatives 11. 5-Alkyl-4-azides 11 were not obtained in this manner; however a new one-pot azidation reaction was developed starting from 4-hydroxy derivatives 4 which gave azides 11 in good yields. 4-Azido-5-phenyl derivative 11f cyclized on thermolysis to the indole 12. The thermal behaviour of the azides 11 was studied by thermoanalytical methods (DSC).J. Heterocyclic Chem., 42, 85 (2005).Pyrido[3,2,1-jk]carbazol-6-one is part of the heterocyclic skeleton of many natural products (e.g., strychnos alkaloids such as strychninolones and brucinolones [2], picrasidin Q [3] and olivacine alkaloids [4]). It possesses the biologically interesting combination of indole and 2-pyridone structures. Moreover, some derivatives have found interest in pharmacological [5] or in dye chemistry [6]. Our interest is focused to 4-hydroxy-5-substituted pyrido[3,2,1-jk]carbazol-6-ones (4, 5) which possess 2 reactive positions: the hydroxy group at C-4, which can be substituted by various nucleophiles, and the CH-acidic proton at C-5, which reacts with a large number of electrophiles. In this contribution we want to report an improved synthesis of 4-hydroxy-5-substituted pyrido-[3,2,1-jk]carbazol-6-ones, the acetylation, tosylation and the nucleophilic exchange of the hydroxy groups.The synthesis of some 4-hydroxy-5-substituted pyrido[3,2,1-jk]carbazol-6-ones 4 is described in the literature in a few cases either by thermal condensation of malonates 2 with carbazole 1a at about 300 °C with moderate yields [7], or by thermal condensation of dichlorophenylmalonates with carbazole 1 at 260 °C with good yields [8]. We adopted the cyclocondensation methods of malonates with 1,3-dinucleophiles earlier described for quinolones and related compounds [9] for the synthesis of 4-hydroxy-5-substituted pyrido[3,2,1-jk]carbazol-6-ones 4 and 5. The first reaction step leads in a condensation reaction at about 200 °C to the monoanilides of the carbazole 1a with the malonates 2; the end of this reaction step can be easily observed by the end of ethanol evolution; further thermolysis at higher temperatures (300-350 °C) gives, by elimination of the second equivalent of ethanol, an intermediate α-oxo ketene which attacks in an electrophilic reaction the ortho-position of the aromatic ring to cyclize to the pyrido[3,2,1-jk]carbazol-6-ones 4. The yields of this reaction type are within 60-90% except with the octadecyl malonate 2j; in this case only 24% of 4j was obtained. It was also possible to carry out this reaction in one step without interruption when a 1:1 mixture of the malonate and the carbazole 1a was heated for 12 hours in refluxing diphenyl ether solution which limits the thermolysis temperature to 253 °C. The yields are within 60-80% comparable to the stepwise reaction; the workup however is easier and the purit...

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Zur Chemie des 4-Hydroxy-cumarins

Cited by 11 publications

References 0 publications

Synthesis and reactions of 4‐hydroxy‐8,9,10,11‐ tetrahydropyrido[3,2,1‐jk]carbazol‐6‐ones

Synthesis and reactions of 4‐hydroxy‐8,9,10,11‐ tetrahydropyrido[3,2,1‐jk]carbazol‐6‐ones

Synthesis and Microbiological Activity of Some Newly Synthesized Derivatives of 2‐Oxo‐2H‐chromen‐2‐one

Synthesis and ring closure reactions of pyrido[3,2,1-jk]carbazol-6-ones

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