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Synthesis 2001(9): 1351-1355
DOI: 10.1055/s-2001-15221
DOI: 10.1055/s-2001-15221
PAPER
© Georg Thieme Verlag Stuttgart · New York
An Efficient Synthesis of Substituted Quinolines
Further Information
Received
26 October 2000
Publication Date:
24 September 2004 (online)
Publication History
Publication Date:
24 September 2004 (online)
Abstract
The addition of substituted anilines to ”vinamidinium" bis-tetrafluoroborate salt 1 [2-dimethylaminomethylene-1,3-bis(dimethylimmonio)propane bis-tetrafluoroborate], followed by cyclization of the resulting imino-eneamine salt and hydrolysis of the masked aldehydes 2, provide the corresponding 3-formyl quinolines 3. While the condensation of both 1 and its analogous bis-perchlorate salt and amidines are known to provide pyrimidines, we believe this is the first example of a quinoline annulation sequence with ”vinamidinium" bis-tetrafluoroborate salt 1 and anilines.
Key words
anilines - condensation - cyclizations - quinolines - ”vinamidinium" bis-tetrafluoroborate salt
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