Reaction of 1,3-Oxazinium Salt with Active Methylene Compounds

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概要

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• 2,4,6-Triphenyl-1,3-oxazinium perchlorate reacts with active methylene compounds to give several butadiene derivatives and various pyridine derivatives. The reactions seem to proceed as follows: The carbanion from an active methylene compound attacks the 6-position of the oxazinium ring, and opens the ring to form a butadiene as an intermediate, which is then recyclized to a pyridine derivative according to a characteristic mode. The mode of recyclization differs with the constituent of each active methylene. There are five modes characteristic of cyano-, ester-, amido- and benzoyl constituents and nitromethane. A compound containing two different constituents usually follows either of the two possible modes.

• 公益社団法人 日本化学会の論文

著者

• Shibuya Isao

  National Chemical Laboratory for Industry

• Kurabayashi Masahiro

  National Chemical Laboratory for Industry

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• The reaction of 2,4,6-triphenyl-1,3-thiazinylium perchlorate with active methylenes.
• The reaction of 1,3,5-triazine with aromatic nitrile oxides. A new synthesis of 3-substituted 1,2,4-oxadiazoles.

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