A practical procedure for the selective N-alkylation of 4-alkoxy-2-pyridones and its use in a sulfone-mediated synthesis of N-methyl-4-methoxy-2-pyridone

Tetrahedron Letters

Volumn 46, Issue 46, 2005, Pages 7917-7920

  Conreaux, David ^a   Bossharth, Emmanuel ^a   Monteiro, Nuno ^a   Desbordes, Philippe ^b   Balme, Geneviève ^a  

^a UNIVERSITÉ LYON 1   (France)

^b BAYER AG   (Germany)

Author keywords

4 Alkoxy 2 pyridones; Desulfonylation; N Alkylation; Tetrabutyl ammonium iodide

Indexed keywords

4 METHOXY 1 METHYL 2 PYRIDONE; N METHYL 4 METHOXY 2 PYRIDONE; POTASSIUM DERIVATIVE; POTASSIUM TERT BUTOXIDE; PYRIDONE DERIVATIVE; SULFONE DERIVATIVE; TETRABUTYLAMMONIUM; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CATALYSIS; CATALYST; SYNTHESIS;

EID: 26844457596     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.09.095     Document Type: Article

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43. 3, 300 MHz). 11b : δ 7.42-7.27 (m, 10H); 7.13 (d, J = 7.5 Hz, 1H); 6.05 (d, J = 2.6 Hz, 1H); 5.95 (dd, J = 2.6 and 7.5 Hz, 1H); 5.09 (s, 2H); 4.99 (s, 2H). 11c : δ 7.30-7.25 (m, 5H); 7.03 (d, J = 7.35 Hz, 1H); 5.90-5.75 (m, 3H); 5.16 (dd, J = 1.3 and 10.2 Hz, 1H); 5.10 (d, J = 1.3 and 17.1 Hz, 1H); 4.89 (s, 2H); 4.41 (dt, J = 1.3 and 5.65 Hz, 2H). 11d : δ 7.48 (d, J = 7.5 Hz, 1H); 7.40-7.35 (m, 5H); 6.03 (dd, J = 2.6 and 7.5 Hz, 1H); 5.98 (d, J = 2.6 Hz, 1H); 4.98 (s, 2H); 4.68 (d, J = 2.6 Hz, 2H); 2.47 (t, J = 2.6 Hz, 2H). 11e : δ 7.45 (s, 1H); 7.40-7.30 (m, 11H); 7.14 (m, 4H); 7.02 (d, J = 7.9 Hz, 1H); 6.08 (d, J = 2.6 Hz, 1H); 5.93 (dd, J = 2.6 and 7.9 Hz, 1H); 4.99 (s, 2H). 11f : δ 7.35-7.25 (m, 5H); 7.11 (d, J = 7.5 Hz, 1H); 5.97 (d, J = 2.8 Hz, 1H); 5.89 (dd, J = 2.8 and 7.5 Hz, 1H); 5.09 (s, 2H); 3.76 (s, 3H). 11g : δ 7.05 (d, J = 8.3 Hz, 1H); 5.81 (m, 2H); 3.79 (t, J = 7.4 Hz, 3H); 3.68 (s, 3H); 1.62 (m, 2H); 1.28 (m, 2H); 0.87 (t, J = 7.4 Hz, 3H).
44. M.A. Pérez, J.L. Soto, F. Guzman, and A. Diaz Synthesis 1984 1045 1047
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