Bimolecular reduction of 9-alkyl-3-nitrocarbazoles
-
J. Kyzioł
Abstract
Reduction of 9-alkyl-3-nitrocarbazoles (Ia–Ie) with lithium aluminium hydride gave corresponding 9,9′-dialkyl-3,3′-azocarbazoles (IIa–IIe) in moderate yield. By the action of zinc dust in alcohol and aqueous alkali on I or II, 5,13-dialkyldiindolo[3,2-a,d]phenazines (IIIa–IIId) were obtained. Parent compounds, viz. 3,3′-azocarbazole (IIf) and diindolo[3,2-a,d]phenazine (IIIf) could not be obtained in these ways. Compound IIf was obtained in Vorländer reaction and IIIf by thermal decomposition of 3-azidocarbazole. Formation of IIIa–IIId is explained as a result of ortho-benzidine rearrangement of hypothetical 9,9′-dialkyl-3,3′-hydrazocarbazoles.
[1] Fry, A. J., in The Chemistry of Amino, Nitroso and Nitro Compounds (Patai, S., Editor), p. 319. Wiley, Chichester, 1982. Suche in Google Scholar
[2] Sidgwick, N. V., Organic Chemistry of Nitrogen, 3rd Edition, p. 387. Clarendon Press, Oxford, 1966. Suche in Google Scholar
[3] Kyzioł, J. B. and Woźniak, P., Pol. J. Chem. 55, 961 (1981). Suche in Google Scholar
[4] Fanghänel, E., Behrman, K., Bouwe, E., Kyzioł, J. B., and Wacławek, W., Z. Chem. 24, 286 (1984). http://dx.doi.org/10.1002/zfch.1984024080310.1002/zfch.19840240803Suche in Google Scholar
[5] Boyer, J. H., in The Chemistry of the Nitro and Nitroso Groups, Part 1 (Feuer, H., Editor), p. 215. Interscience Publishers, New York, 1969. Suche in Google Scholar
[6] Kyzioł, J. B., J. Heterocycl. Chem. 22, 1301 (1985). Suche in Google Scholar
[7] Kyzioł, J. B. and Daszkiewicz, Z., Tetrahedron 40, 1857 (1984). http://dx.doi.org/10.1016/S0040-4020(01)91140-810.1016/S0040-4020(01)91140-8Suche in Google Scholar
[8] Atkinson, E. R. and Lawer, H. J., Org. Synth., Coll. Vol. 1, 222 (1932). Suche in Google Scholar
[9] Atkinson, E. R., Murphy, D. M., and Lufkin, J. E., Org. Synth., Coll. Vol. 4, 872 (1963). Suche in Google Scholar
[10] Sandler, S. R. and Karo, W., Organic Functional Group Preparation, Vol. 2, p. 320. Academic Press, New York, 1971. Suche in Google Scholar
[11] Chan, T.-W. D. and Tam, S. W., in The Chemistry of the Hydrazo, Azo, and Azoxy Groups, Vol. 2 (Patai, S., Editor), p. 105. Wiley, Chichester, 1997. http://dx.doi.org/10.1002/0470023503.ch410.1002/0470023503.ch4Suche in Google Scholar
[12] Jaffé, H. H. and Gardner, R. W., J. Am. Chem. Soc. 80, 319 (1958). http://dx.doi.org/10.1021/ja01535a01710.1021/ja01535a017Suche in Google Scholar
[13] Yeh, S. J. and Jaffé, H. H., J. Am. Chem. Soc. 81, 3279 (1959). http://dx.doi.org/10.1021/ja01522a03110.1021/ja01522a031Suche in Google Scholar
[14] McClellan, A. L., Tables of Experimental Dipole Moments. W. H. Freeman, San Francisco, 1963. Suche in Google Scholar
[15] Horner, L. and Dehnert, J., Chem. Ber. 96, 786 (1963). http://dx.doi.org/10.1002/cber.1963096031910.1002/cber.19630960319Suche in Google Scholar
[16] Shine, H. J., Aromatic Rearrangements, p. 126. Elsevier, New York, 1967. Suche in Google Scholar
[17] Lukashevich, V. O., Tetrahedron 23, 1317 (1967). http://dx.doi.org/10.1016/0040-4020(67)85084-110.1016/0040-4020(67)85084-1Suche in Google Scholar
© 2007 Institute of Chemistry, Slovak Academy of Sciences
Artikel in diesem Heft
- Determination of potassium in fatty acid methyl esters applying an ion-selective potassium electrode
- Selective solid-phase extraction of Cu(II) using freshly precipitated lead diethyldithiocarbamate and its spectrophotometric determination
- Evaluation of colon cancer elements contents in serum using statistical methods
- Determination of norfloxacin in pharmaceuticals, human serum, and urine using a luminol—dissolved oxygen chemiluminescence system
- Properties of fructosyltransferase from Aureobasidium pullulans immobilized on an acrylic carrier
- Influence of two-phase system composition on biocatalytic properties of β-galactosidase preparations
- Thermal decomposition kinetics of strontium oxalate
- Synthesis and properties of lanthanide(III) complexes with 4-hydroxy-3,5-dimethoxybenzoic acid
- Influence of photoinitiator and curing conditions on polymerization kinetics and gloss of UV-cured coatings
- Interactions in iron gall inks
- Bimolecular reduction of 9-alkyl-3-nitrocarbazoles
- A detailed analysis of volatile constituents of Aquilegia pancicii Degen, a Serbian steno-endemic species
- A one-pot synthesis of 8-amino-1-methoxy-6H-dibenzo[b,d]pyran-6-one
- Magnetically modified bentonite as a possible contrast agent in MRI of gastrointestinal tract
Artikel in diesem Heft
- Determination of potassium in fatty acid methyl esters applying an ion-selective potassium electrode
- Selective solid-phase extraction of Cu(II) using freshly precipitated lead diethyldithiocarbamate and its spectrophotometric determination
- Evaluation of colon cancer elements contents in serum using statistical methods
- Determination of norfloxacin in pharmaceuticals, human serum, and urine using a luminol—dissolved oxygen chemiluminescence system
- Properties of fructosyltransferase from Aureobasidium pullulans immobilized on an acrylic carrier
- Influence of two-phase system composition on biocatalytic properties of β-galactosidase preparations
- Thermal decomposition kinetics of strontium oxalate
- Synthesis and properties of lanthanide(III) complexes with 4-hydroxy-3,5-dimethoxybenzoic acid
- Influence of photoinitiator and curing conditions on polymerization kinetics and gloss of UV-cured coatings
- Interactions in iron gall inks
- Bimolecular reduction of 9-alkyl-3-nitrocarbazoles
- A detailed analysis of volatile constituents of Aquilegia pancicii Degen, a Serbian steno-endemic species
- A one-pot synthesis of 8-amino-1-methoxy-6H-dibenzo[b,d]pyran-6-one
- Magnetically modified bentonite as a possible contrast agent in MRI of gastrointestinal tract
