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Report | Regular issue | Vol 23, No. 7, 1985, pp.1635-1638
Published online, 1st January, 1970
DOI: 10.3987/R-1985-07-1635
Reaction of N-Alkylheteroaromatic Cation with Phosphite

Isao Takeuchi, Yasuhiro Shinata, and Yoshiki Hamada*

*Faculty of Pharmacy, Meijo University, 150 Yagotoyama, Tenpaku, Nagoya 468-8503, Japan

Abstract

Treatment of N-methylquinolinium iodide (1) with trimethyl phosphite afforded dimethyl N-methyl-1,4-dihydroquinoline-4-phosphonate (3), whereas when 1 was treated with dimethyl sodiophosphonate, dimethyl N-methyl-1,2-dihydroquinoline-2-phosphonate (2) was obtained. The 2-phosphonate (2) underwent thermal rearrangement to the more stable 4-phosphonate (3). Similar results were obtained with some analogous heteroaromatics.