Heterocycles p. 2071 - 2081 (2005)
Update date:2022-08-02
Topics:
Yao, Jiangchao
Blake, Paul R.
Yang, Ji
On the reaction 3-bromo-4-nitropyridine with amine, three in stead of two expected products are separated. 2D NMR spectral data indicate the major product was an unexpected nitro-group migration product. To explore the rearrangement mechanism, a systematic study with various solvents and bases was undertaken. Results obtained indicate that nitro-group migration occurs in polar aprotic solvents; while expected nucleophilic substitution took place under all tested conditions.
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