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[Reaction of 3-aryl-2-nitroacrylates With Titanium Tetrachloride. Formation of 4H-1,2-oxazines and Hydroxy-Arylaldehydes]

[Reaction of 3-aryl-2-nitroacrylates With Titanium Tetrachloride. Formation of 4H-1,2-oxazines and Hydroxy-Arylaldehydes]

S Hirotani, S Zen

Yakugaku Zasshi. 1994 Apr;114(4):272-6.

PMID: 8201549

Abstract:

The reaction of ethyl 3-aryl-2-nitroacrylate (1a: aryl = 3-methoxyphenyl) with toluene in the presence of titanium tetrachloride gave 4-(4'-methyl-phenyl)-4H-1,2-benzoxazine (3) in a 44.2% yield. The acrylate 1a reacted with dichloromethane in the presence of titanium tetrachloride to give 5-methoxy-salicylaldehyde (2a) in a 61.8% yield. Therefore, 2a was presumed to be formed via an intermediate 4H-1,2-benzoxazine (3'), followed by ring opening to quinone methide and cyano formate. In a similar reaction using both toluene and dichloromethane, 1 bearing a 2-naphthyl group gave a dimer of quinone methide and 1-hydroxy-2-naphthaldehyde via 4H-naphth[2,1-e]-1,2-oxazine, respectively.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP52684341	2-Naphthyl acrylate		52684-34-1	Price

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