- A concise Friedl?nder/Buchwald-Hartwig approach to the total synthesis of quindoline, a bioactive natural indoloquinoline alkaloid, and toward the unnatural 10-methylquindoline
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A new approach toward the synthesis of quindoline, a recognized indoloquinoline alkaloid, is reported. The sequence comprises the synthesis of 2-(2-nitrophenyl)quinoline through an optimized Friedl?nder condensation of 2-amino benzaldehyde with 2-nitroacetophenone, followed by the selective C-3 bromination of the quinoline moiety to direct the cyclization, reduction of the nitro group and a final Buchwald-Hartwig cyclization. In addition, quindoline was also converted to the unnatural 10-methylquindoline by reaction with dimethyl carbonate under DBU promotion. It was found that the non-directed reductive cyclization of 2-(2-nitrophenyl)quinoline results in indazolo[2,3-a]quinoline, instead of yielding quindoline. DFT calculations were employed to explain this reaction outcome; this finding suggested that the result of a previously reported total synthesis of quindoline should be revised.
- Méndez, María V.,Simonetti, Sebastian O.,Kaufman, Teodoro S.,Bracca, Andrea B. J.
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- An alternative synthesis of quindoline and one of its closely related derivatives
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The alkaloid Quindoline (13) and one of its tetracyclic isomer indazolo[2,3-a]quinoline (8) have been synthesised utilising the Pd(0)- catalysed cross-coupling reaction of pivaloylamino phenylboronic acid (2) with substituted quinolines.
- Csanyi,Timari,Hajos
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p. 3959 - 3969
(2007/10/03)
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