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One-pot synthesis of 2-aminoquinoline-based alkaloids from acetonitrile.

Organic & biomolecular chemistry (2012-05-24)
Takashi Tomioka, Yusuke Takahashi, Toshihide Maejima
ABSTRACT

α-Diaminoboryl carbanions, readily prepared from acetonitrile, stereoselectively convert 2-nitrobenzaldehydes into nitrophenyl (Z)-acrylonitriles. Subsequent reductive cyclization leads to a series of 2-aminoquinoline derivatives. The entire procedure is practically operated in a single flask.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Acrylonitrile, ≥99%, contains 35-45 ppm monomethyl ether hydroquinone as inhibitor
Supelco
Acrylonitrile, analytical standard
Sigma-Aldrich
Acrylonitrile, ≥99%, contains 35-45 ppm monomethyl ether hydroquinone as inhibitor
Supelco
Acrylonitrile solution, certified reference material, 5000 μg/mL in methanol