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Communication | Regular issue | Vol 81, No. 9, 2010, pp.2057-2062
Published online, 30th July, 2010
DOI: 10.3987/COM-10-12006
Microwave Assisted Rapid Preparation of N-Alkyl-2-pyridones under Neutral Conditions by Hilbert-Johnson Reaction

Hirokazu Iida,* Machiko Suda, Etsuko Nakajima, Hiroko Hakamatsuka, Yuka Nagashima, Kouta Joho, Kenta Amemiya, Tatsuya Moromizato, Kiyoshi Matsumoto, Yasuoki Murakami, and Hiroshi Hamana*

*Faculty of Pharmaceutical Sciences, Chiba Institute of Science, 3 Shiomi-cho, Choshi, Chiba 288-0025, Japan


The reactions of 2-methoxypyridine with haloalkanes without solvent and catalyst under microwave irradiation (100-200 °C, 5 min) yielded the corresponding N-alkyl-2(1H)-pyridones in good to moderate yields. However, the reactions were sensitive to length of haloalkanes. In contrast, the reactions of 2-alkoxypyridines with corresponding iodoalkanes under microwave irradiation (150 °C) proceeded rapidly without catalyst and solvent, and were complete within 5 min to afford N-alkyl-2(1H)-pyridones in good to excellent yields.