Abstract
11H-Indolo[3,2-c]quinolin-6-ones, which are containing the γ-carboline ring system, can be easily synthesized from 4-azido-3-phenyl-2(1H)-quinolones, which are obtained in a two step reaction from 4-hydroxy-3-phenyl-2(1H)-quinolones. Cyclization of the azides can be realized by irradiation or thermal reaction.
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Diese Arbeit ist die 4. Mitt. der Serie „Organische Azide in der Heterocyclen-Synthese“. 3. Mitt.:Stadlbauer W (1986) Monatsh Chem 117: 1305
Saxton JE (1960) In:Manske (Hrsg) Bd VII. Academic Press, New York London, S 4 ff
Hörlein U (1954) Chem Ber 87: 463
Boeckelheide V, Ainsworth C (1950) J Amer Chem Soc 72: 2132
Clemo GR, Perkin WH (1925) J Chem Soc 1925: 1608
Kermack WO, Smith JF (1930) J Chem Soc 1930: 1999
Kermack WO, Storey NE (1950) J Chem Soc 1950: 607
Winterfeldt E, Altmann HJ (1968) Angew Chem 80: 486. Angew Chem, Int Ed Engl 7: 466
Bergmann J, Carlsson R, Sjöberg B (1977) J Heterocycl Chem 14: 1123
Bourdais J, Lorre A (1973) J Heterocycl Chem 12: 1111
Dave V, Warnhoff EW (1975) Tetrahedron 31: 1255
Kanaoka Y, San-nohe K (1980) Tetrahedron Lett 21: 3893
DeDiesbach H, Gross J, Tschannen W (1951) Helv Chim Acta 34: 1050
Walser A, Silverman G, Flynn T, Fryer RI (1975) J Heterocycl Chem 12: 351
Stadlbauer W, Kappe Th (1984) Monatsh Chem 115: 467
Braunholtz JT, Mann FG (1955) J Chem Soc 1955: 381
Dyall LK (1983) In:Patai S, Rappoport Z (eds) The chemistry of functional groups, Suppl D. Wiley, Chichester.
Smith PAS (1984) In:Scriven EFV (ed) Azides and nitrenes. Academic Press, New York London
Iddon B, Meth-Cohn O, Scriven EFV, Suschitzky H, Gallagher PT (1979) Angew Chem 91: 965 und dort zitierte Literatur
Baumgarten P, Kärgel W (1927) Ber Dtsch Chem Ges 60: 832;Stadlbauer W, Schmut O, Kappe Th (1980) Monatsh Chem 111: 1005
Bickoff EM, Lyman RL, Livingstone AL, Botth AN (1958) J Amer Chem Soc 80: 3969;Emerson OH, Bickoff EM (1958) J Amer Chem Soc 80: 4391;Bickoff EM, Botth AN (1958) J Agricult Food Chem 6: 536
Grisebach H, Barz W (1963) Chem Ind (London) 1963: 690
Simonisch E, Eisenhut W, Stamm OA, Schmid H (1960) Helv Chim Acta 43: 58
Wattenberg LW, Lam LKT, Fladmoe AV (1979) Cancer Res 39: 1651
Maksiumi Y (1973) Jpn Pat 73.000596; Chem Abstr 78: 72091
Padfield EM, Tomlinson ML (1950) J Chem Soc 1950: 2272
Sharkova NM, Kucherova NF, Zagorevskii VA (1962) Zh Org Khim 32: 364
Unangst PC, Brown RE (1984) J Heterocycl Chem 21: 283
Staudinger H, Meyer J (1919) Helv Chim Acta 2: 635
Sasaki T, Kanematsu K, Murarta M (1972) Tetrahedron 28: 2383
Vaultier M (1968) Tetrahedron Lett 24: 763
Rolla F (1982) J Org Chem 47: 4372
Stadlbauer W, Kappe Th (1982) Monatsh Chem 113: 751
Stadlbauer W, Schmut O, Kappe Th (1980) Monatsh Chem 111: 1005
Mentzer C, Molho D, Vercier P (1949) Bull Soc Chim (France) 1949: 749;Mentzer C, Vercier P (1957) Monatsh Chem 88: 264
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Stadlbauer, W., Karem, AS. & Kappe, T. Eine einfache Synthese von 11H-Indolo[3,2-c]chinolin-6-onen. Monatsh Chem 118, 81–89 (1987). https://doi.org/10.1007/BF00810043
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DOI: https://doi.org/10.1007/BF00810043