CsOH-Catalyzed Synthesis of Benzazole and Related Heterocyles from Nitriles

来源 :中国化学会第十三届全国有机合成化学学术研讨会 | 被引量 : 0次 | 上传用户:xingxing123789
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  Heterocycle compounds are important building blocks in pharmaceuticals,bioactive molecules,natural products,agrochemical compounds,and materials.We have previously reported alcohol-based t-BuONa-catalyzed1 and amine-based CuI-catalyzed2 aerobic oxidative cyclocondensation reactions of o-thio/hydroxy/aminoanilines for the synthesis of benzazole heterocycles.However,these methods are mainly limited to the reactions of o-thio/hydroxy/aminoanilines but not suitable for β-aminoethanols,1,2-diamines,and β-aminoethanethols.And,the reactions of o-hydroxyanilines were not efficient enough,giving only low yields of the target benzoxazoles.Thus,new methods for efficient synthesis of benzoxazoles and oxazolines are still highly desirable in the field.We have also observed CsOH-catalyzed hydration and aminolysis reactions of nitriles with water,ammonia,primary and secondary amines for clean synthesis of primary to tertiary amides) Based on these studies,we now developed a CsOH-catalyzed cyclocondensation reaction of nitriles with o-thio/hydroxyanilines,β-aminoethanols,and β-aminoethanethols,providing a new method for efficient synthesis of these heterocycle compounds.
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