Warianty tytułu
Reactivity of Heterocyclic N-oxides : Reaction Involving a Substituent
Języki publikacji
Abstrakty
W części poświęconej odtleniającej substytucji nukleofilowej wykazano, że zachodzi ona zwykle w pozycji α. Gdy obecna jest grupa metylowa w pozycji a lub γ, reakcja przebiega w łańcuchu bocznym. (fragment tekstu)
Deoxidative nucleophilic substitution involving a carbon-linked substituent is formally an intramolecular redox process in that the alkyl group is oxidized while the oxygen of the N-oxide group is lost. Reaction 2-picoline 1-oxide with acetic anhidride yields 2-acetoxymethylpyridine, and to a lesser degree on the nucleus, yielding 3- and 5-acetoxy-2-methylpyridine as minor products. Side-chain acétoxylation of N-oxides in particular in the case of 2-picoline N-oxides is a convient source hydroxymethylpyridines. The alkyl groups adjacent to the heterocyclic ring in α- and γ-substituted azines show a significant acidity and several reaction based on the attack of the corresponding carboanion onto various electrophiles have been developed e.g. base-catalyzed deuterium exchange, condensation of α- and γ-methyl N-oxides with aldehydes, reaction with alkyl nitrites and oxidation of methyl groups to aldehydes, chemical reduction of nitro group to azoxy, azo, hydrazo, hydroksylamino and amino group with no N-deoxygenation are carried out. This paper is the review of 44 articles. (original abstract)
Rocznik
Tom
Numer
Strony
75--81
Opis fizyczny
Twórcy
autor
- Akademia Ekonomiczna we Wrocławiu
autor
- Akademia Ekonomiczna we Wrocławiu
Bibliografia
- Abramovitch R.A., Saha J.C.: Advances in Heterocyclic. Chemistry Academic, New York 1966.
- Sammes P.G., Serra-Errante G., Tinker A.C.: J. Chem. Soc., Perkin Trans., I, 853 (1978).
- Bobrański B., Kochańska L., Kowalewska A.: Ber., 71, 2385 (1983).
- Bauer L., Gardella L.A.: J. Org. Chem., 28, 1323 (1963).
- Tsai C.Y., Sha C.K.: Tetrahedron Lett., 1419 (1987).
- Hayashi E., Shimada N.: Yakugaku Zasshi, 98, 1503 (1978).
- Schichri K. (i in.): Chem. Pharm. Bull., 28, 493 (1980).
- Oshawa A., Kawaguchi T., Igeta H.: J. Org. Chem., 47, 3497 (1982).
- Gallagher A.I., Lalinsky B.A., Cuper C.M.: J. Org. Chem., 35, 1175 (1970).
- Zatsepina N.N. (i in.): Reakts. Sposobnost Org. Soedin., 9, 745 (1972).
- Goto Y. (i in.): Chem. Pharm. Bull., 30, 1126 (1982).
- Kaiser E.M.: Tetrahedron, 39, 2055 (1983).
- Ohsawa A., Uezu T., Igeta H.: Yakugaku Zassi, 100, 774 (1980).
- Brzeziński B.: Pol. J. Chem., 57, 249 (1983).
- Sakamoto T. (i in.): Heterocycles, 17, 73 (1982).
- Yamanaka H., Ogawa S., Konno S.: Chem. Pharm. Bull., 28,1526 (1980).
- Iwamura H. (i in.): J. Am. Chem. Soc., 92, 7474 (1970).
- Neuenhoeffer H., Metz H.J.: Liebigs Ann. Chem., 1476 (1983).
- Sakamoto T., Sakaai T., Yamanaka H.: Chem. Pharm. Bull., 29,2485 (1981).
- Achremowicz L.: Tetrahedron Lett., 2433 (1980).
- Majewski P., Bodalski R., Michalski J.: Sythesis, 140 (1971).
- Nishikawa M. (i in.): Chem. Pharm. Bull., 28, 2436 (1980).
- Archer G.A., Sternbach L.H.: Chem. Rev., 68, 747 (1968).
- Stempel A., Reeder E., Sternbach L.H.: J. Org. Chem., 30, 4267 (1965).
- Broadbent H.S., Anderson R.C., Kuchar M.C.J.: J. Heterocycl. Chem., 14, 289 (1977).
- Mizuno Y., Endo T.: J. Org. Chem., 43, 684 (1978).
- Kobayashi Y., Kumadaki I., Taguchi S.: Chem. Pharm. Bull., 19, 624 (1971).
- Suzuki I., Nakashima T., Nagasawa N.: Chem. Pharm. Bull., 14, 816 (1966).
- Morita I. (i in.): Yakugaku Zasshi, 95, 954 (1975).
- Kataoka N. (i in.): Bull. Chem. Soc. Jap., 40, 62 (1967).
- Lister J.E., Tieckelman H.: J. Am. Chem. Soc., 90, 4361 (1968).
- Maurer M., Orth W., Fickert W.: Chem. Abst., 93, 239253s (1980).
- Sega T. (i in.): J. Org. Chem., 38, 3307 (1973).
- Gardner J.N., Katritzky A.R.: J. Chem. Soc., 4375 (1957).
- Bojarska-Dahlig H.N.: Rec. Trav. Chim. Pays-Bas, 78, 981 (1959).
- Ochiai E. (i in.): Yakugaku Zasshi, 65, 5/6A,1 (1945).
- Ochiai E., Hayashi E.: Yakugaku Zasshi, 67, 151 (1947).
- Newbold G.T., Spring F.S.: J. Chem. Soc., 1864 (1948).
- Ochiai E., Hayashi E.: Yakugaku Zasshi, 67, 154 (1947).
- Nakagome T.: Yakugaku Zasshi, 82, 244 (1962).
- Nakagome T.: Yakugaku Zasshi, 82, 1206 (1962).
- Sedova V.F., Mustafina T.Y., Mamaev V.P.: Khim. Geterotsikl. Soedin., 1515 (1981).
- Gewald K., Buchwalder M., Peukert M.: Prakt. Chem., 315, 679 (1973).
- Schoellkopf U., Driessler F.: Justus Liebigs Ann. Chem., 1521 (1975).
- Barlos K. (i in.): J. Org. Chem., 50, 696 (1985).
Typ dokumentu
Bibliografia
Identyfikatory
Identyfikator YADDA
bwmeta1.element.ekon-element-000171186770