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2005
Pyrazine derivatives
R 0550
Practical Synthesis of 1-Aryl-6-(hydroxymethyl)-2-ketopiperazines via a 6-exo
Cyclization. — The title method allows the synthesis of target com06- 151 Amide—Epoxide
pound (VII) with good yield and on a larger scale. The reaction is applicable to the
variety of electron-rich N-aryl acetamides (VIII), but not for substrates with electron-withdrawing groups [cf. (X) and 4-CN or 4-NO2 analogues]. In this case the cyclization is promoted by NaH and demonstrated by the synthesis of (XII). — (POWELL*,
N. A.; CISKE, F. L.; CLAY, E. C.; CODY, W. L.; DOWNING, D. M.; BLAZECKA, P.
G.; HOLSWORTH, D. D.; EDMUNDS, J. J.; Org. Lett. 6 (2004) 22, 4069-4072;
Pfizer Global Res. Dev., Ann Arbor, MI 48105, USA; Eng.) — Steudel
2005
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