Abstract:Die Tetrahydrochinolone (I) reagieren mit Natriumazid in Trichloressigsäure bei 60°C zu den 1,4‐Diazepinonen (II), von denen (IIa) mit Lithiumaluminiumhydrid zum 1,4‐Diazepin (III) reduziert wird.
“…Synthetic 6-oxopyrroloquinolines 3 utilize one of two general approaches, involving either the construction of a pyrrole ring on to a quinoline by a standard indole synthesis, [7][8][9][10][11][12][13][14] or the construction of a new six-membered ring between N1 and C7 of an indole. 1,[15][16][17][18][19][20][21][22] Synthesis of both natural and unnatural flavonoids have been widely studied because of their extensive biological properties. [23][24][25][26][27][28][29][30][31][32] Incorporation of the indole nucleus within the flavonoid structure leads to 6-oxopyrroloquinolines, which could be derived from indoles.…”
Section: Introductionmentioning
confidence: 99%
“…As yet there appears to be no report of any naturally occurring 6-oxopyrroloquinoline. Synthetic 6-oxopyrroloquinolines 3 utilize one of two general approaches, involving either the construction of a pyrrole ring on to a quinoline by a standard indole synthesis, − or the construction of a new six-membered ring between N1 and C7 of an indole. ,− …”
7-Acetyl-4,6-dimethoxy-3-phenylindole 10 was converted into a range of 7-indolyl chalcones 13 by reaction with aryl aldehydes under basic conditions. Oxidation of the chalcones 13 with alkaline hydrogen peroxide gave the isolable epoxides 14, which were cyclized with further base treatment into the indole flavonols, or 5-hydroxy-6-oxopyrroloquinolines 15. The related compounds 25 and 26, examples of indole flavanones and flavones, respectively, were also synthesized. UV spectroscopic comparisons between flavonoids and indole flavonoids are discussed.
“…Synthetic 6-oxopyrroloquinolines 3 utilize one of two general approaches, involving either the construction of a pyrrole ring on to a quinoline by a standard indole synthesis, [7][8][9][10][11][12][13][14] or the construction of a new six-membered ring between N1 and C7 of an indole. 1,[15][16][17][18][19][20][21][22] Synthesis of both natural and unnatural flavonoids have been widely studied because of their extensive biological properties. [23][24][25][26][27][28][29][30][31][32] Incorporation of the indole nucleus within the flavonoid structure leads to 6-oxopyrroloquinolines, which could be derived from indoles.…”
Section: Introductionmentioning
confidence: 99%
“…As yet there appears to be no report of any naturally occurring 6-oxopyrroloquinoline. Synthetic 6-oxopyrroloquinolines 3 utilize one of two general approaches, involving either the construction of a pyrrole ring on to a quinoline by a standard indole synthesis, − or the construction of a new six-membered ring between N1 and C7 of an indole. ,− …”
7-Acetyl-4,6-dimethoxy-3-phenylindole 10 was converted into a range of 7-indolyl chalcones 13 by reaction with aryl aldehydes under basic conditions. Oxidation of the chalcones 13 with alkaline hydrogen peroxide gave the isolable epoxides 14, which were cyclized with further base treatment into the indole flavonols, or 5-hydroxy-6-oxopyrroloquinolines 15. The related compounds 25 and 26, examples of indole flavanones and flavones, respectively, were also synthesized. UV spectroscopic comparisons between flavonoids and indole flavonoids are discussed.
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