244610-88-6Relevant articles and documents
Electron and Hydrogen Transfer Reductions of Some 2,4-Disubstituted Pyridines
Attia, A.,El-Salam, O. I. Abd,Youssef, T. E.
, p. 351 - 362 (2007/10/03)
New synthesis of 2,4-diacetylpyridine 1 was undertaken by Claisen condensation of 2,4-diethoxycarbonylpyridine 2a with ethyl acetate, followed by hydrolysis of the intermediate 3. Reduction of 1 with zinc or its salt in hydrochloric, formic or acetic acids afforded mixtures of the ketocarbinol 4 dicarbinol 5 or diethyl 6 pyridine derivatives. Formation of 6 as the complete reduction product was chemically proved to proceed via 4 and 5. Electrochemical reduction of 2a leads to 2,4-dimethylpyridine 7, and that of 1 gave rise to a mixture of 5 and 6 along with 2,4-diethyl-1,2,5,6-tetrahydropyridine 8 and 2,4-diethylpiperidine 9. Finally, metal hydride reduction of 1 gave 5, and that of diesters 2 or diacid chloride 10 derivatives afforded 2,4-dihydroxymethylpyridine 11.
