Construction of the quinoline ring system by application of minisci radical cyclization

ORGN 752

Ryan N. Burgin1, Simon Jones, simon.jones@sheffield.ac.uk1, Amy Smith2, and Brian Tarbit2. (1) Department of Chemistry, University of Sheffield, Sheffield, S3 7HF, United Kingdom, (2) Vertellus Specialties UK Limited, Seal Sands Road, Middlesbrough, TS2 1UB, United Kingdom
A non-classical route towards the quinoline skeleton has been devised that involves a Minisci reaction to perform the key cyclisation step. Sonogashira coupling between 3-bromopyridine 1 and malonate derivative 2 gives an alkyne 3 which is then selectively reduced to an alkene. This is decarboxylated under Minisci conditions to form a radical that cyclizes to afford the quinoline or tetrahydroquinoline ring system. Application of this methodology to other bicyclic aromatic heterocycles is also described.

 

Combinatorial, Parallel and Process Chemistry, Heterocycles, Aromatics, New Reactions and Methodology
8:00 PM-10:00 PM, Wednesday, August 22, 2007 BCEC -- Exhibit Hall - B2, Poster

Division of Organic Chemistry

The 234th ACS National Meeting, Boston, MA, August 19-23, 2007