Products from metallation and attempted metallation of 1-alkyl-4,6-diphenyl-2-pyridones and subsequent reaction with electrophiles

Katritzky, Alan R.; Grzeskowiak, Nicholas E.; Salgado, Hector J.; Bahari, Zakaria bin

doi:10.1016/s0040-4039(00)92197-x

Cited by 8 publications

(1 citation statement)

References 2 publications

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“…(2 H, q, J 6 . 5 Hz, CH2Me), and 1.10(3 H, t, J6.5 Hz, CH2Me); m/z 137 ( M + ' , 37), 123 (loo), 108 (21), 94 (84), and 82 (6); followed closely by 1,2-dimethyl-4-pyridone (14c) (43%) as a pale yellow crystalline solid; h,,,,(EtOH) 262 nm (log E 4.29); h,,,. (EtOH + HCl) 242 nm (log E 4.02); v,,,.…”

Section: -Lithio-1 -Rnethyl-2-pyridone Andmentioning

confidence: 99%

Ring lithiation of pyridones

Meghani¹,

Joule²

1988

J. Chem. Soc., Perkin Trans. 1

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Lithiation of 1 -methyl-2-pyridone takes place mainly at the methyl group which then leads to a dimer (11) by addition to a second mol equivalent of pyridone at C-6. Lithiation of 1 -methyl-4-pyridone takes place cleanly and efficiently at C-2; this lithio derivative gave a dimer (13) with a second mol equivalent of the pyridone and reacted with a variety of carbon electrophiles to produce 2-substituted 4-pyridones (14c-n).1 -Methoxymethyl-, 1 -benzyloxymethyl-, and 1 -(2-trimethylsilylethoxy)methyl-4-pyridones also lithiate at C-2, though these lithio derivatives were much less reactive towards electrop h i les. * This paper had not been abstracted by Chemical Abstracts up to the end of Volume 103, 1985. We thank Professor Katritzky for calling our attention to this paper after the publication of our preliminary communication. 24

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Section: -Lithio-1 -Rnethyl-2-pyridone Andmentioning

confidence: 99%

Ring lithiation of pyridones

Meghani¹,

Joule²

1988

J. Chem. Soc., Perkin Trans. 1

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ChemInform Abstract: PRODUCTS FROM METALATION AND ATTEMPTED METALATION OF 1‐ALKYL‐4,6‐DIPHENYL‐2‐PYRIDONES AND SUBSEQUENT REACTION WITH ELECTROPHILES

KATRITZKY¹,

Grzeskowiak²,

Salgado³

et al. 1981

Chemischer Informationsdienst

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Pyridone Functionalization: Regioselective Deprotonation of 6‐Methylpyridin‐2(1H)‐ and ‐4(1H)‐one Derivatives

et al. 2016

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Selective functionalization at the α‐methyl group of 1‐substituted pyridin‐2(1H)‐ and 4(1H)‐ones (2‐ and 4‐pyridones) can be achieved by appropriate choice of base. n‐Butyllithium was found to effect clean 6(2)‐methyl deprotonation of 1‐benzyl‐2‐ and ‐4‐pyridone derivatives, while potassium hexamethyldisilazide (KHMDS) was the preferred reagent for methyl deprotonation of the corresponding 1‐methyl‐2‐ and ‐4‐pyridones. Deprotonation proceeds smoothly at –78 °C, and the resulting anions react readily with a wide range of electrophiles (aldehydes, ketones, alkylating reagents, and an azo compound) under precise temperature control to form usefully functionalized 2‐ and 4‐pyridones and quinolizinones.

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Products from metallation and attempted metallation of 1-alkyl-4,6-diphenyl-2-pyridones and subsequent reaction with electrophiles

Cited by 8 publications

References 2 publications

Ring lithiation of pyridones

Ring lithiation of pyridones

ChemInform Abstract: PRODUCTS FROM METALATION AND ATTEMPTED METALATION OF 1‐ALKYL‐4,6‐DIPHENYL‐2‐PYRIDONES AND SUBSEQUENT REACTION WITH ELECTROPHILES

Pyridone Functionalization: Regioselective Deprotonation of 6‐Methylpyridin‐2(1H)‐ and ‐4(1H)‐one Derivatives

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