Tandem benzannulation ring-closing metathesis strategy for the synthesis of benzo-fused nitrogen heterocycles

ORGN 941

Xiao Yin Mak, xymak@mit.edu, Aimee L. Crombie, acrombie@mit.edu, and Rick L. Danheiser. Department of Chemistry, Massachusetts Institute of Technology, Cambridge, MA 02139
A tandem strategy for the synthesis of polycyclic benzo-fused nitrogen heterocycles will be described. The reaction of ynamides with vinylketenes leads via a pericyclic cascade process to highly-substituted aniline derivatives which are subsequently transformed via ring-closing metathesis to dihydroquinoline, benzoazepine, and benzoazocine derivatives. The mechanism, scope, and limitations of this new tandem strategy will be discussed.

 

Heterocycles and Aromatics
8:00 AM-12:00 PM, Thursday, August 23, 2007 BCEC -- 254 A/B, Oral

Division of Organic Chemistry

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