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  • 1995-1999  (3)
  • 1980-1984  (5)
  • 1975-1979  (6)
  • 1
    ISSN: 1520-6904
    Source: ACS Legacy Archives
    Topics: Chemistry and Pharmacology
    Type of Medium: Electronic Resource
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  • 2
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Oxidative Rearrangement of Chalcones by Thallium(III) Nitrate, IV. The Synthesis of Dalpatin, Fujikinin, Glycitein and of Other Natural IsoflavonesThe synthesis of 7-hydroxy-2′,6-dimethoxy-4′,5′ -methylenedioxysoflavone-7-O-β-D-glucopyranoside (dalpatin, 1), 7-hydroxy-6-methoxy-3′,4′-methylenedioxyisoflavone (fujikinetin, 4), its 7-O-β-D-glucopyranoside (fujikinin, 6), 4′,7-dihydroxy-6-methoxyisoflavone (glucitein, 35), 6-hydroxy-2′,7-dimethoxy-4′,5′-methylenedioxy-(7) and 5,6,7-trimethoxy-3′,4′-methylenedioxyisoflavone (9), two constituents of Cordyla africana, further of 5,6,7,8-tetramethoxy-3′,4′-methylenedioxyiso-flavone (10) is described. 10 was not identical with an isoflavone from C. africana for which the same structure has been proposed.
    Notes: 7-Hydroxy-2′,6-dimethoxy-4′,5′-methylendioxyisoflavon-7-O-β-D-glucopyranosid (Dalpatin, 1), 7-Hydroxy-6-methoxy-3′,4′-methylendioxyisoflavon (Fujikinetin, 4), sein 7-O-β-D-glucopyranosid (Fujikinin, 6), 4′,7-Dihydroxy-6-methoxyisoflavon (Glycitein, 35) und zwei Inhaltsstoffe von Cordyla africana (6-Hydroxy-2′,7-dimethoxy-4′,5′-methylendioxy- (7) und 5,6,7-Trimethoxy-3′,4′-methylendioxyisoflavon (9)), weiterhin 5,6,7,8-Tetramethoxy-3′,4′-methylendioxyisoflavon (10) wurden hergestellt. 10 war mit einem Isoflavon aus C. africana, für das die gleiche Struktur vorgeschlagen worden war, nicht identisch.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
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  • 3
    Electronic Resource
    Electronic Resource
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 81 (1998), S. 754-763 
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The CH2Cl2 extract of Monotes engleri Gilg. (Dipterocarpaceae) showed antifungal activity against the yeast Candida albicans in our bioautographic TLC assays. After a first fractionation of the crude extract, the bioactivity was located in one of the fractions. To perform an efficient targeted isolation of the active compounds, LC/UV/MS and LC/UV/NMR analyses of the crude extract and the active fraction were performed. LC/UV/, LC/MS, and LC/NMR data (1D and 2D) allowed the identification of 1 as (2S)-2,3-dihydro-5,7-dihydroxy-{3-hydroxy-4-[(3-methylbut-2-enyl) oxy]phenyl}-4H-1-benzopyran-4-one, a new prenylated flavanone, named monoteson A. Subsequent isolation of 1 has permitted the determination of its absolute configuration on the basis of CD measurements. Theree other prenylated flavanoes 2-4 were isolated from the same extract. Compound 3 was identified as 2- (3, 5-dihydroxyphenyl) -2,3-dihydro-5, 7-dihydroxy-6, 8-bis (3-methylbut-2-enyl)-4 H-1-benzopyran-4-one, another new natural product, named monotesone B. The structures of 2 and 4 were established as selinone and lonchocarpol A, respectively. The antifungal activity against Candida albicans was determined for all compounds.
    Additional Material: 6 Ill.
    Type of Medium: Electronic Resource
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  • 4
    Electronic Resource
    Electronic Resource
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 109 (1976), S. 3811-3816 
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Oxidative Rearrangement of Chalcones by Thallium(III) Nitrate, VI1 Synthesis of the Isoflavonoids Jamaicin and LeiocarpinInertness of the 2,2-dimethyl-2H-chromene system towards oxidation by Tl(NO3)3 makes possible the synthesis of the isoflavone jamaicin (1) and of the pterocarpan leiocarpin (4) from 6-acetyl-5-hydroxy-2,2-dimethyl-2H-chromene (9) by oxidative rearrangement of the corresponding chalcones (6,8).
    Notes: Die Unempfindlichkeit des 2,2-Dimethyl-2H-chromen-Systems gegen Oxidation mit TI(NO3)3 ermöglichte die von 6-Acetyl-5-hydroxy-2,2-dimethyl-2H-chromen (9) ausgehende Synthese des Isoflavons Jamaicin (1) und des Pterocarpans Leiocarpin (4) durch oxidative Umlagerung der entsprechenden Chalcone (6, 8).
    Type of Medium: Electronic Resource
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  • 5
    ISSN: 1434-193X
    Keywords: Hypervalent iodine ; Phenols ; Oxidation ; Cyclohexa-2,4-dienones ; Dimerization ; Asatone ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Oxidation of the 2-methoxyphenols 1c-f with phenyliodonium(III) diacetate (PIDA) in methanol resulted in the formation of the cyclohexa-2,4-dienones 4c-f, which dimerized spontaneously to a single product (5c-f) in each case. Using this method the synthesis of asatone (5a) and its demethoxy analogue (5b) was also accomplished starting from the readily available phenol derivatives 1a and 1b, respectively.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
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  • 6
    Electronic Resource
    Electronic Resource
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 112 (1979), S. 480-483 
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: A Novel Biomimetic Transformation of Chalcone Glycosides to Isoflavone GlycosidesAcetates of chalcone glucosides were oxidatively rearranged by thallium(III) nitrate in CH(OMe)3/, MeOH and the products cyclized with sodium methoxide to isoflavone glucosides. The pterocarpan medicarpin β-D-glucopyranoside (4) was prepared in an optically pure form.
    Notes: Acetate von Chalcon-glucosiden wurden mit Thallium(III)-nitrat in CH(OMe)3/MeOH oxidativ umgelagert und die Produkte mit Natriummethylat zu Isoflavon-glucosiden cyclisiert. Das Pterocarpan Medicarpin-β-D-glucopyranosid (4) wurde in optisch reiner Form hergestellt.
    Type of Medium: Electronic Resource
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  • 7
    Electronic Resource
    Electronic Resource
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 112 (1979), S. 3879-3885 
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Ring Contraction of 2,2-Dimethyl-2H-chromenes by Oxidation with Thallium(III) Nitrate. The Synthesis of CorylinExcept for the 5-acetoxy derivatives, which react very slowly, 2,2-dimethyl-2H-chromenes and 3,4-dihydro-2H-pyran are oxidized smoothly with TI(NO3)3. 2 H2O in methanol to give generally by ring contraction -3(dimethoxymethyl)-2,3-dihydrobenzofurans and -2(dimethoxymethyl)-tetrahydrofuran, respectively. Ring-contracted products were isolated as by-products in the synthesis of the pyranoisoflavone corylin (11).
    Notes: Mit Ausnahme der 5-Acetoxy-Derivate, die nur sehr langsam reagieren, unterliegen 2,2-Dimethyl-2H-chromene und 3,4-Dihydro-2H-pyran einer glatten Oxidation mit T1(NO3)3. 3H2O in Methanol, die im allgemeinen durch Ringverengung zu -3(Dimethoxymethyl)-2,3-dihydrobenzo-furanen bzw. -2(Dimethoxymethyl)tetrahydrofuran führt. Ringverengte Verbindungen wurden bei der Synthese des Pyranoisoflavons Corylin (11) als Nebenprodukte isoliert.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
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  • 8
    ISSN: 0947-3440
    Keywords: Cyclodehydrogenation ; 2′-Hydroxychalcones ; Flavones ; Iodosobenzene diacetate ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: A new synthesis of chrysin (1) and luteolin (4) was accomplished by the cyclodehydrogenation of the appropriately substituted 2′-hydroxychalcones 21 and 22 in the presence of iodosobenzene diacetate/potassium hydroxide in methanol. The scope and limitation of this transformation is discussed.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
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  • 9
    Electronic Resource
    Electronic Resource
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1980 (1980), S. 1271-1282 
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Oxidation of 1,3-Diphenyl-1,3-propanediones with Thallium(III) Nitrate in MethanolOn oxidation with thallium(III) nitrate in methanol, 1,3-diphenyl-1,3-propanediones 1 rearrange to give 3-oxo-2,3-diphenylpropanoic esters 2 and products derived therefrom. However, 1-(2-hydroxyphenyl)-3-phenyl-1,3-propanediones 1h-k undergo oxidative cyclization to 2-aroyl-3(2H)-benzofuranones 5. The alkali and acid catalysed cleavage of 5 is discussed.
    Notes: Bei der Oxidation mit Thallium(III)-nitrat in Methanol werden die 1,3-Diphenyl-1,3-propandione 1 zu den 3-Oxo-2,3-diphenylpropansäureestern 2 und deren Folgeprodukte umgelagert. Die 1-(2-Hydroxyphenyl)-3-phenyl-1,3-propandione 1h-k werden dagegen oxidativ zu den 2-Aroyl-3(2H)-benzofuranonen 5 cyclisiert.  -  Der durch Alkalilauge und Säure katalysierte Abbau von 5 wird diskutiert.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
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  • 10
    Electronic Resource
    Electronic Resource
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1983 (1983), S. 2247-2261 
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Circular Dichroism, LXXXI. - Synthesis and Circular Dichroism of Steroids with an Isochromanone ChromophoreStarting from cholesterol the three possible stereoisomeric isochromanes 10-12 have been synthesized; their oxidation gave the corresponding lactones 13-15. The → π* band of the isochromanone („benzoic acid ester“) chromophore could unequivocally be identified in the CD spectra between 245 and 265 nm. For its Cotton effect the same helicity rule is valid as for homochirally analogous 1-tetralones: its sign, and also that of the Cotton effect within the α band of the otherwise not substituted benzene chromophore, is opposite to that of the torsional angle (O=)C—C(=Ctransoid); the sign of the Cotton effect within the „conjugation band“ is the same as that of this torsional angle. The correlation between absolute configuration and CD of natural isochromanone derivatives is discussed: only for the Cotton effect within the n → π* band the mentioned helicity rule is independent of the substitution of the benzene ring. The invalidity of the helicity rule of chiral tetralins for homochirally analogous isochromanes can be explained with the help of Petruska's „q values“.
    Notes: Ausgehend von Cholesterin wurden die drei möglichen stereoisomeren Isochromane 10-12 synthetisiert, die durch Oxidation die entsprechenden Lactone 13-15 ergaben. Die n → π*-Bande des Isochromanon-(„Benzoesäureester“-)Chromophors konnte in den CD-Spektren zwischen 245 und 265 nm eindeutig identifiziert werden. Für ihren Cotton-Effekt gilt die gleiche Helizitätsregel wie für homochiral analoge 1-Tetralone: sein Vorzeichen sowie das des Cotton-Effekts innerhalb der α-Bande des sonst unsubstituierten Benzolchromophors ist entgegengesetzt zum Vorzeichen des Torsionswinkels (O=)C—C(=Ctransoid); das Vorzeichen des Cotton-Effekts innerhalb der “Konjugationsbande“ ist gleich dem dieses Torsionswinkels. Der Zusammenhang zwischen absoluter Konfiguration und CD natürlicher Isochromanonderivate wird diskutiert: nur für den Cotton-Effekt innerhalb der n → π*-Bande ist die genannte Helizitätsregel von der Benzolring-substitution unabhängig. Die Ungültigkeit der Helizitätsregel chiraler Tetraline für homochiral analoge Isochromane kann mit Hilfe der „q-Werte“ von Petruska erklärt werden.
    Additional Material: 7 Ill.
    Type of Medium: Electronic Resource
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