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2005
Pyridine derivatives
R 0380
Activation of Pyridinium Salts for Electrophilic Acylation: A Method for Converof Pyridines into 3-Acylpyridines. — An indirect one-pot method for the 3-acy12- 148 sion
lation of pyridines via the intermediate N-Mom pyridinium salts is described. The
method utilized the cyanide ion as a temporary nucleophile to form an activated, electron-rich dihydropyridine intermediate that is susceptible to acylation at the 3-position,
and subsequent aromatization. However, the method is only applicable to highly reactive acylating agents like trichloroacetyl chloride, or ethyl oxalyl chloride. For reduction of compound (VII) the stronger cyanophile AgOTf is necessary to obtain quinoline
(VIII). — (KLAPARS, A.; VEDEJS, E.; Chem. Heterocycl. Compd. (N. Y.) 40 (2004)
6, 759-766; Dep. Process Res., Merck Res. Lab., Merck&Co., Inc., Rahway, NJ 07065,
USA; Eng.) — Bartels
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