Synthesis of [e]-ferrocenyl-4-aminopyrimidine: A redox active analogue of adenine

ORGN 636

Haofan Wang, hwang1@jhsph.edu1, Nhu-Y T. Stessman2, Uzma I. Zakai, zakaiu@email.arizona.edu3, Rafal Kaminski1, and Richard S. Glass, rglass@u.arizona.edu3. (1) Department of Chemistry, University of Arizona, Tucson, AZ 85721, (2) Department of Chemistry, California State University, Stanislaus, 801 W. Monte Vista Ave., Turlock, CA 95382, (3) Department of Chemistry, The University of Arizona, P O Box 210041, 1306 E. University Blvd., Tucson, AZ 85721-0041
In the duplex structure of DNA the bases are pi–stacked. This raises the interesting question of whether there can be rapid, long-range conduction of electrons through the pi-system. A redox active analogue of adenine, [e]-ferrocenyl-4-aminopyrimidine, 1, in which the aminopyrimidine moiety is annulated to a cyclopentadienyl ring of ferrocene, was designed. A regio- and stereo- selective synthesis of 1 was achieved starting with ferrocenecarboxaldehyde in 15 steps with an overall yield of 8%. A Curtius rearrangement was used to form the key intermediate (s)-2-formylferrocenylbenzylcarbamate. The structure of 1 was established by an x-ray crystallographyic study.

 

Asymmetric Reactions, Heterocycles, Aromatics, Combinatorial, and Physical Organic Chemistry
8:00 PM-10:00 PM, Wednesday, 31 August 2005 Washington DC Convention Center -- Hall A, Poster

Division of Organic Chemistry

The 230th ACS National Meeting, in Washington, DC, Aug 28-Sept 1, 2005