Convergent synthesis of 6-substituted phenanthridines via anionic ring closure

TY - JOUR

T1 - Convergent synthesis of 6-substituted phenanthridines via anionic ring closure

AU - Lysén, M.

AU - Kristensen, Jesper Langgaard

AU - Vedsø, P.

AU - Begtrup, M.

PY - 2002/1/1

Y1 - 2002/1/1

N2 - Chemical equation presented The addition of organometallic derivatives to the cyano group of 2-(2-fluorophenyl)benzonitrile followed by intramolecular nucleophilic substitution produces 6-substituted phenanthridines. Alkyllithiums, aryllithiums, and sterically nondemanding lithium amides reacted at -78 °C to produce the 6-substituted phenanthridines in 82-98% yield upon warming to room temperature. The addition of the corresponding Grignard reagents requires an excess of the organometallic reagent and extented reaction times at elevated temperature.

AB - Chemical equation presented The addition of organometallic derivatives to the cyano group of 2-(2-fluorophenyl)benzonitrile followed by intramolecular nucleophilic substitution produces 6-substituted phenanthridines. Alkyllithiums, aryllithiums, and sterically nondemanding lithium amides reacted at -78 °C to produce the 6-substituted phenanthridines in 82-98% yield upon warming to room temperature. The addition of the corresponding Grignard reagents requires an excess of the organometallic reagent and extented reaction times at elevated temperature.

UR - http://www.scopus.com/inward/record.url?scp=0009303718&partnerID=8YFLogxK

U2 - 10.1021/ol0170051

DO - 10.1021/ol0170051

M3 - Journal article

AN - SCOPUS:0009303718

SN - 1523-7060

VL - 4

SP - 257

EP - 259

JO - Organic Letters

JF - Organic Letters

IS - 2

ER -