ORGN 505 |
| The versatile intermediates, 3-(4-halo-2-iodo)phenyl)sydnones (2), have been synthesized in good yield by dilithiation of 3-(4-halophenyl)sydnones (1) using BuLi or LDA where appropriate, trapping with I2, followed by reduction at the 4-position with Na2SO3. Subsequent coupling of 2 with phenyl acetylene under Sonogashira conditions followed by Suzuki coupling at the 4'-position yields various ortho-phenylethynyl sydnones (3). Reactions of 3 with electrophiles have been explored as avenues to novel sydnoquinolines (4). The scope and limitations of these processes will be discussed.
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Heterocycles, Aromatics, Metal-Mediated Reactions and Syntheses, Materials, Devices, and Switches
8:00 PM-10:00 PM, Wednesday, 29 March 2006 Georgia World Congress Center -- Ex. Hall B4, Poster
Division of Organic Chemistry |
