Preparation method of naphthotriazolodiazepineketone compound

Abstract

The invention relates to a preparation method of a naphthotriazolodiazepineketone compound, which comprises the following steps: carrying out a reaction on N-(8-X-naphthalene-1-yl) propiolamide used as a starting raw material (X = Br, I) with sodium azide under heating conditions, and separating and purifying the reaction product to obtain the target compound, naphthotriazolodiazepineketone. The naphthotriazolodiazepineketone is synthesized by adopting a one-step method, and the method has the advantages of mild reaction conditions, short reaction time, convenience in operation and the like. An effective synthetic route is provided for application research of the compound in the aspects of biological medicines, materials, pesticides and fine chemicals, so that the invention has an important potential application value.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and relates to a method for preparing naphthotriazolodiazepine compounds, namely naphthalene[1,8-ef][1,2,3]triazole[1,5 -a] The preparation method of [1,4]diazepine-8(7H)-one compound. Background technique [0002] Benzodiazepines and triazoles are important heterocyclic structures commonly found in many natural products, bioactive compounds and pharmaceuticals. 1,4-Benzodiazepine is considered the most important drug-dominant scaffold, and it has dominated the treatment of central nervous system (CNS) diseases for the past 40 years. In recent years, modifying 1,4-benzodiazepines with other heterocycles is a common strategy to adjust their biological activity and selectivity. Recent literature shows that the splicing body of 1,4-benzodiazepine skeleton and 1,2,3-triazole has good biological activity and can be used as protease inhibitor (Mohapatra, D.K.et alBioorg.Med.Chem. Lett. 2009, 19, 524...

AI Technical Summary

Problems solved by technology

Over the past few decades, several synthetic methods have been developed for the synthesis of benzotriazolodiazepinones, such as Akritopoulou-zanze et al. using the Ugi reaction and the [3+2] alkyne-azide Synthetic benzotriazolodiazepine compound (Tetrahedron Lett, 2004,45,8439), the shortcoming of this method is to need to prepare the isocyanide with malodorous smell and the organic azide compound of explosion hazard, this Method not suitable for mass production

Vachhani, D.D. et al. use Ugi reaction and copper catalyzed [3+2] alkyne-sodium azide to synthesize benzodiazepine ketones. Catalyst, this synthesis method is also not suitable for large-scale production (Eur.J.Org.Chem.2013,2013,1223)

In summary, these traditional methods have some limitations, including the need to pre-introduce the azide group (-N 3 ), harsh reaction conditions and limited range of substrates, etc.

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