- Polyfunctional pyridines from nitroacetamidine and β-diketones. A useful synthesis of substituted imidazo[4,5-b]pyridines and related compounds
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Nitroacetamidine undergoes a useful cyclocondensation with β-diketones to produce substituted 2-amino-3-nitropyridines. Use of an acylpyruvate generates hitherto unreported 2-amino-3-nitropyridine-4-carboxylates. These may be converted easily to functionalized imidazo[4,5-b]pyridines and oxazolo[5,4-b]pyridines.
- Batt,Houghton
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p. 963 - 969
(2007/10/02)
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- Nitroketenaminals, VII: Synthesis of substituted 2-amino-3-nitropyridines from 1,3-biselectrophiles and 2-nitroethen-1,1-diamine
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The reaction of the enones 1a-f with the nitroketenaminal 2 leads to the 4,6-disubstituted 2-amino-1,4-dihydro-3-nitropyridines 3a-f. Compounds 3a-c,f are oxidized in low yields by air to the pyridines 4a-c,f.-5- and 6-substituted 2-amino-3-nitropyridines (9a,b and 11) can be prepared from 2, 8a,b, and 10, respectively.
- Troschutz,Luckel
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p. 785 - 789
(2007/10/02)
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