ORGN 389 |
Synthesis of 3-oxy-1,7-naphthyridine and its tetrahydro and dihydro derivatives
| Yahua Liu, Wenshan Li, and Lawrence M Sayre. Department of Chemistry, Case Western Reserve University, 10900 Euclid Ave., Cleveland, OH 44106 |
The preparation of the 3-oxy-1,7-naphthyridine core and its dihydro and tetrahydro derivatives are described. 3-Benzyloxy-1,7-naphthyridine (1) was constructed efficiently by the Friedlander reaction of 3-aminoisonicotinaldehyde with PhCH2OCH2CH=O, and its tetrahydro N7-methyl derivative 6 were synthesized by reduction of the regioselectively formed N7 quaternary salt. Naphthyridine 1 underwent HBr-mediated hydrolysis to 3-hydroxy-1,7-naphthyridine 4. The dihydro derivatve 8 was prepared by a two-step oxidation-elimination reaction from 6. |
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Physical Organic, Materials, Heterocycles, Aromatics, Metal-Mediated Reactions
8:00 PM-10:00 PM, Tuesday, September 9, 2003 Hilton New York -- Americas Hall 1, Poster
Division of Organic Chemistry
The 226th ACS National Meeting, New York, NY, September 7-11, 2003
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