Synthesis method of N,N-disubstituted naphtho[2, 1-d]-thiazole-2-amine compound

Abstract

The invention discloses a synthetic method of an N,N-disubstituted naphtho[2, 1-d]-thiazole-2-amine compound. The method comprises the following steps of: reacting 2-naphthylisothiocyanate with a secondary amine compound in a one pot manner under the conditions of oxygen-containing atmosphere and 395-400 nm purple light irradiation to generate an N,N-disubstituted naphtho[2, 1-d]-thiazole-2-aminecompound. The method has the advantages of mild conditions, simple operation, environmental protection, easily available raw materials, excellent compatibility of substrate functional groups, high reaction yield and the like.

Description

technical field [0001] The invention relates to a synthesis method of N,N-disubstituted naphtho[2,1-d]thiazol-2-amine compound, in particular to a method for realizing 2 -A method for the synthesis of N,N-disubstituted naphtho[2,1-d]thiazol-2-amine compounds by tandem addition-cyclization reaction between naphthyl isothiocyanate and secondary amine compounds, which belongs to the synthesis of organic intermediates technology field. Background technique [0002] N,N-disubstituted naphtho[2,1-d]thiazol-2-amine is a polycyclic heteroaromatic compound that plays an important role in the fields of drug development and material chemistry. Secondary amine compound is a very easy-to-obtain raw material. Using secondary amine as an amine source to directly synthesize N,N-disubstituted naphtho[2,1-d]thiazol-2-amine through a one-pot method is an ideal Methods. [0003] In 2017, Professor Fan Xuesen of Henan Normal University reported that a molecular iodine was used as a catalyst, ...

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Problems solved by technology

However, the reaction temperature is high, prone to flammable and explosive hazards, and the reaction product has a moderate yield

[0004] Professor Lei Aiwen from Wuhan University reported a method for the synthesis of N,N-disubstituted naphtho[2,1-d]thiazol-2-amines by electrocatalytic reaction of secondary amines of 2-naphthyl isothiocyanate (Green Chem. .,2017,19,2092–2095), but this method requires the use of a large amount of inorganic salt electrolyte and cumbersome nitrogen protection conditions, and can only use aliphatic amines to synthesize N,N-disubstituted naphtho[2,1-d ]thiazol-2-amine, N-aryl naphtho[2,1-d]thiazol-2-amine cannot be synthesized by aromatic amine, the following reaction (b)

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