Journal of Capital Medical University ›› 2011, Vol. 32 ›› Issue (5): 658-660.doi: 10.3969/j.issn.1006-7795.2011.05.015
• 基础研究 • Previous Articles Next Articles
ZHANG Jian-wei, FAN Yuan-jie
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Abstract: Objective The reactions of quaternary ammoniumsalts of N-heterocycles were investigated. Methods The rearrangement reactions of N-heterocycles might be performed if the N-ylide intermediates can be generated. In compounds containing a β-hydrogen atom, Hofmann elimination may compete and in many cases provides the major product. We tried N-cyanomethyl-N-methylpiperidine bromide and N-cyanomethyl-N-methyltropinone bromide which were treated with sodium hydride. Results The quaternary ammonium salt N-cyanomethyl-N-methylpiperidine bromide furnished the rearrangement reactions products 2-piperidinyl-2-cyanoyl-propionaldehyde and N-cyanomethyl-atropine bromide gave Hofmann elimination product 2-piperidinyl-2-cyanoyl-propionaldehyde. Conclusion Thus we have explored the reaction quaternary ammoniumsalts of N-heterocycles with sodium hydride. Some of them performed Hofmann elimination reactions and some of them underwent rearrangement reactions. N-methylpiperidine and tropinone derivatives were tested. N-methylpiperidine derivative react with sodium borohydride to performed rearrangement reactions. Tropinone derivatives performed Hofmann elimination reaction and cyclize to produce 7.
Key words: quaternary ammoniumsalts, piperidine, rearrangement reactions
CLC Number:
O 62
ZHANG Jian-wei;FAN Yuan-jie. The investigation on the reaction of N-heterocycles[J]. Journal of Capital Medical University, 2011, 32(5): 658-660.
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URL: https://journal03.magtech.org.cn/Jweb_sdykdxxb/EN/10.3969/j.issn.1006-7795.2011.05.015
https://journal03.magtech.org.cn/Jweb_sdykdxxb/EN/Y2011/V32/I5/658