ALBERT

All Library Books, journals and Electronic Records Telegrafenberg

X
feed icon rss

Your email was sent successfully. Check your inbox.

An error occurred while sending the email. Please try again.

Proceed reservation?

Export
  • 1
    Electronic Resource
    Electronic Resource
    Ring Expansion of 2-Alkylidenedihydroquinazolines to Iminodihydro-1,4-benzodiazepines by Methanesulfonyl and Trifluoromethanesulfonyl Azide (2000)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 2000 (2000), S. 1577-1587 
    Details
    ISSN: 1434-193X
    Keywords: Azides ; Cleavage reactions ; Cycloadditions ; Nitrogen heterocycles ; Polycycles ; Ring expansion ; Synthetic methods ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: ---2-Alkyl-1-methylquinazolinium hexafluorophosphates 9 are deprotonated by sodium or potassium hydride to afford solutions of 2-alkylidenedihydroquinazolines 10, which were investigated by NMR spectroscopy. Trapping with methanesulfonyl azide (5a) of 10 in situ or subsequent treatment with trifluoromethanesulfonyl azide (5b) gives mixtures of colourless (15) and intensely yellow N-sulfonylimino-1,4-benzodiazepines 16 along with products due to cleavage of the exocyclic double bond of 10, viz. 11 and 13. The ethylidene compound 10b yields the bicyclic products 18 and 19, apparently by complex sequences of reactions that are triggered by removal of the acidic proton at C-2 of 16b and 16f. The structures of the products are based on spectroscopic evidence and X-ray diffraction analyses performed on 15b, 16d, 16e, and 19.
    Additional Material: 6 Ill.
    Type of Medium: Electronic Resource
    Location Call Number Expected Availability
    BibTip Others were also interested in ...
    Paper (German National Licenses)
  • 2
    Electronic Resource
    Electronic Resource
    Pyrroles from 1,2-Cyclopropanediamines and Aldehydes (1998)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1998 (1998), S. 1645-1652 
    Details
    ISSN: 1434-193X
    Keywords: Azomethine ylides ; Nitrogen heterocycles ; Ring expansion ; Small ring systems ; Synthetic methods ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Mechanistic investigations by means of proton spectroscopy detected intermediates and uncovered the course of reactions in acetate-buffered [D4]methanol of primary cyclopropanediamines cis- and trans-2a with benzaldehyde (3a) or 2,2-dimethylpropanal (3b), of secondary cyclopropanediamines cis- and trans-2b with 3b, and of the ring-methylated cyclopropanediamine trans-14a and the aromatic aldehydes 3a and c. This study provided the basis of an expedient synthesis of pyrroles which takes place under exceptionally mild conditions. Irrespective of the configuration, primary (2a·2HBr) and secondary cyclopropanediammonium dibromides 2b and c·2HBr that are devoid of ring substituents react with aromatic aldehydes 3a, e-h, cinnamic aldehyde (3i), and 3b to afford 2-substituted (8a, b) and 1,2-disubstituted pyrroles (8c-i), respectively. The 3-substituted secondary trans-cyclopropanediammonium dibromides 24·2HBr furnish 1,2,4-trisubstituted pyrroles 25. While the primary 1-methylcyclopropanediammonium dibromide trans-14a·2HBr reacts regioselectively with 3a and c to produce only 2,3-substituted pyrroles 19a, c, the corresponding secondary dibromide trans-14c·2HBr gives rise to the formation of mixtures of 1,2,3- (22) and 1,2,5-trisubstituted pyrroles 23. The key step of pyrrole formation from 1,2-cyclopropanediamines and aldehydes is the ring expansion of intermediate monoiminium ions of type 5 via azomethine ylides (E, Z)-6 to yield dihydropyrrolium ions 7.
    Type of Medium: Electronic Resource
    Location Call Number Expected Availability
    BibTip Others were also interested in ...
    Paper (German National Licenses)
  • 3
    Electronic Resource
    Electronic Resource
    Ring Expansion of 2-Alkylidenedihydroquinolines to 2-Iminodihydro-1-benzazepines by Phenyl, Methanesulphonyl, and Trifluoromethanesulphonyl Azide[1] (2000)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 2000 (2000), S. 507-520 
    Details
    ISSN: 1434-193X
    Keywords: Azides ; Cleavage reactions ; Cycloadditions ; Nitrogen heterocycles ; Photolysis ; Ring expansion ; Spiro compounds ; Synthetic methods ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: ---2-Alkyl-1-methylquinolinium hexafluorophosphates 1 are deprotonated by sodium or potassium hydride to afford solutions of 2-alkylidenedihydroquinolines 2, which are investigated by NMR spectroscopy. 1,3-Dipolar cycloaddition of phenyl azide to 2 yields the spirocyclic products 10. While, at 80-110 °C, the [3 + 2] cycloaddition that afforded (u)-10f is reversible and accompanied by epimerisation to give (l)-10f, thermolysis of the dimethyl compounds 10b and d affords the ring-expanded products 14b and d, respectively, in good yields along with molecular nitrogen. Irradiation of 10d with light of λ 〉 320 nm results in the formation of similar amounts of 14d and [3 + 2] cycloreversion products, viz. 2-diazopropane (5b) and the N-phenylimine 15d. - Trapping of 2 by methanesulphonyl azide (18a) gives mixtures of the products of ring expansion (21b, d-f, 10-50 %) and [3 + 2] cycloreversion (22a, d, 10-80 %) of the apparently very labile intermediate spirocyclic cycloadducts 19. The ratio of 21 vs. 22 is significantly improved when 18a is replaced by trifluoromethanesulphonyl azide (18b), which affords the iminodihydrobenzazepines 21i-k in 50-75 % yield. The structures of the products are based on NMR evidence and X-ray diffraction analyses performed with 21b, d, and (ax,E)-21e.
    Additional Material: 4 Ill.
    Type of Medium: Electronic Resource
    Location Call Number Expected Availability
    BibTip Others were also interested in ...
    Paper (German National Licenses)
  • 4
    Electronic Resource
    Electronic Resource
    Ring Expansion vs. Cleavage of the Exocyclic Double Bond of 2-Cycloalkylidenedihydrobenzothiazoles and -benzimidazoles by Methanesulfonyl Azide (2000)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 2000 (2000), S. 1229-1233 
    Details
    ISSN: 1434-193X
    Keywords: Azides ; Cleavage reactions ; Cycloadditions ; Nitrogen heterocycles ; Ring expansion ; Sulfur heterocycles ; Synthetic methods ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -Deprotonation of the 2-cycloalkylbenzothiazolium perchlorates 1f-h with sodium hydride in the presence of methanesulfonyl azide (3) affords the spirocyclic dihydro-1,4-benzothiazines 9f-h together with small amounts of the 2-iminobenzothiazole 5. The 2-cycloalkylidenedihydrobenzimidazoles 11e-h are generated by deprotonation with potassium hydride from the corresponding 2-cycloalkylbenzimidazolium salts 10e-h, and trapped with 3 to yield the zwitterions 12e-h. Whereas 12h is thermally unstable, 12e-g are isolated and thermolysed at 20-80 °C. The cyclopropyl zwitterion 12e decomposes in an ill-defined way, only at temperatures above 80 °C. In contrast, 12f,g, and, in particular, 12h, decompose more readily to furnish the products of ring expansion (13f-h) and those of a [3 + 2] cycloreversion (6 and 14) of intermediate spirocyclic triazolines. Products that might be indicative of the intervention of hypothetical zwitterions of type 8 cannot be detected.
    Additional Material: 4 Tab.
    Type of Medium: Electronic Resource
    Location Call Number Expected Availability
    BibTip Others were also interested in ...
    Paper (German National Licenses)
  • 5
    Electronic Resource
    Electronic Resource
    An Attempted Synthesis of 2,6-Bis(phenylazo)barbaralane (1997)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1997 (1997), S. 1733-1738 
    Details
    ISSN: 0947-3440
    Keywords: Azo compounds ; Cyclizations ; Hydrazones ; Michael additions ; Nitrogen heterocycles ; Oxidations ; Polycycles ; Rearrangements ; Strained molecules ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Treatment of the unsaturated ketone 6 with phenylhydrazine fails to afford the unsaturated phenylhydrazone 3 but gives the tricyclic phenylhydrazoketone exo-8, which is oxidised with iron(III) chloride to yield the phenylazoketone exo-9. The configuration of exo-9 is elucidated with the help of an X-ray diffraction analysis. The unsaturated phenylazo compound 14 is obtained from Meerwein's diketone 10 in two ways. Iodination of the phenylhydrazone 11 in the presence of pyridine followed by elimination of pyridinium iodide from the bispyridinium salt 13 with aqueous sodium hydroxide in dimethyl sulphoxide furnishes 14 in low yield. A somewhat better yield is more conveniently achieved when the dibromodiketones exo,exo- and exo,endo-12 are allowed to react with phenylhydrazine in the presence of pyridine. Bromination of 14 with N-bromosuccinimide in cyclohexane as solvent affords the labile dibromide 15. Both reagents employed, viz. the zinc/copper couple in refluxing tetrahydrofuran and butyllithium at low temperature, fail to convert 15 into the hoped-for bis(phenylazo)barbaralane 1 but instead give rise to the formation of the isomer 17, either by cyclisation of the intermediate anion 16 or by rearrangement of 1.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.199719970815
    Location Call Number Expected Availability
    BibTip Others were also interested in ...
    Paper (German National Licenses)
    Fulltext
Close ⊗
This website uses cookies and the analysis tool Matomo. More information can be found here...