Abstract
Derivatives of [1]benzothieno[2.3—d]isoxazole, a new heterocyclic ring system, were synthesized by 1.3-dipolar cyclisations: benzo[b]thiophene-1.1-dioxide and its 3-methyl derivative reacted with nitrile oxides and nitrones to the corresponding substituted [1]benzothieno[2.3—d]isoxazolines and-isoxazolidines. Hydrogenolysis of the latter cleaved the isoxazolidine ring, yielding the corresponding 2-(α-phenylamino-benzyl)-3-hydroxy-2.3-dihydro-benzo[b]thiophene-1.1-dioxides.
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Literatur
F. Sauter, Mh. Chem.99, 1507, 2100 (1968);101, 535 (1970);F. Sauter undW. Deinhammer, Mh. Chem.104, 1593 (1973).
F. Sauter undW. Deinhammer, Mh. Chem.104, 1586 (1973).
F. Sauter, Mh. Chem.99, 1591 (1968).
Allgem. Übersicht:R. Huisgen, Angew. Chem.75, 604 (1963).
R. Huisgen undW. Mack, Tetrahedron Letters1961, 583;R. Huisgen, W. Mack undE. Anneser, Tetrahedron Letters1961, 587.
Hergestellt nachH. Wieland undL. Semper, Ber. dtsch. chem. Ges.39, 2522 (1906).
O. H. Wheeler undP. H. Gore, J. Amer. chem. Soc.78, 3363 (1956).
R. Grashey, R. Huisgen undH. Leitermann, Tetrahedron Letters1960, Nr. 12, 9.
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Herrn Prof. Dr.E. Hardegger zum 60. Geburtstag gewidmet.
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Sauter, F., Büyük, G. Synthese von [1]Benzothieno[2,3—d]isoxazol-Derivaten. Monatshefte für Chemie 105, 254–260 (1974). https://doi.org/10.1007/BF00907370
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DOI: https://doi.org/10.1007/BF00907370