Preparation method of dihydrooxazinyl naphthalene compound

Abstract

The invention relates to a preparation method of a dihydrooxazinyl naphthalene compound. The method comprises the following steps: adding a catalyst, paraformaldehyde, an arylamine compound and naphthol into water in sequence; fully reacting at the temperature of 20-80 DEG C to obtain reaction liquid; performing extracting, drying, concentrating and column chromatography isolation on the reaction liquid in sequence according to a conventional method to obtain a product I or a product II, wherein the structure formula of the product is shown in the specifications. The method has the advantages of mild conditions, short reaction time, easiness in operation, high yield, environmental friendliness, realization of scale production and good industrial application prospect.

Description

technical field [0001] The invention relates to the field of organic synthetic chemistry, in particular to a preparation method of naphthodihydrooxazine compounds. Background technique [0002] Naphthalene dihydroxazine compounds have certain biological activities, so they are of great use in the synthesis of medicines, such as the synthesis of anticancer drugs, antibacterial drugs and anti-HIV virus drugs. In addition, naphthodihydroxazine compounds can also be used to prepare phenolic polymers. Such polymers have good mechanical properties and electrical properties, so they have generally attracted people's attention at home and abroad. [0003] At present, a better method for synthesizing naphthodihydroxazines is a three-component reaction of naphthol, formaldehyde or paraformaldehyde and aromatic amines. The reaction has high atom utilization due to the formation of water as the only by-product. In 2010, Shingare et al. used tetrabutylammonium bromide as a phase transf...

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Problems solved by technology

In 2010, Shingare et al. used tetrabutylammonium bromide as a phase transfer catalyst, sodium bisulfate as an additive, and an ionic liquid as a solvent to react β-naphthol, formaldehyde aqueous solution and aromatic amines at 60°C to form naphthobis Hydroxazine compounds, although the reaction time is short and the yield can reach 90%, but the post-reaction treatment is more troublesome and the reaction conditions are more complicated (Journal of the Korean Chemical Society, 2010, 54, 437)

In 2012, Tae et al. used boron trifluoride supported on silica as a catalyst under the condition of ultrasonic radiation to promote the reaction of β-naphthol, formaldehyde aqueous solution and aromatic amine compounds to form naphthodihydrooxazine compounds, although the reaction The yield of boron trifluoride can reach 90% in a short period of time, but boron trifluoride is unstable, highly toxic, and dangerous to operate (Journal of Chemical Research (Chemical Research), 2012, 36, 398)

In 2011, Shingare et al. used PEG-400 as a solvent at room temperature to react naphthol, formaldehyde aqueous solution and aromatic amines to generate naphthodihydrooxazines. Although the product yield can reach 92%, when naphthalene The phenol is α-naphthol, and when the benzene ring of the arylamine compound contains a nitro substituent, the reaction cannot occur (Chinese Chemical Letters (Chinese Chemical Letters), 2011, 22, 915), and the scope of substrate application is limited

[0004] So far, using zero-valent metal as catalyst and water as reaction solvent, paraformaldehyde, aromatic amine compound and naphthol are used to prepare naphthodihydro in one pot The reaction of oxazine compounds has not been reported in the literature

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