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2,4,6-三取代-1,3,5-三嗪的原子经济性合成:以NHI作为唯一氮源,铁催化醛的环化反应

Atom-efficient synthesis of 2,4,6-trisubstituted 1,3,5-triazines Fe-catalyzed cyclization of aldehydes with NHI as the sole nitrogen source.

作者信息

Xiao Jiang, Ren Shuang, Liu Qiang

机构信息

State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University Changsha 410082 P.R. China

出版信息

RSC Adv. 2020 Jun 9;10(37):22230-22233. doi: 10.1039/d0ra03323e. eCollection 2020 Jun 8.

Abstract

An atom-efficient, straightforward method for the synthesis of 2,4,6-triaryl-1,3,5-triazines iron-catalyzed cyclization of aldehydes with NHI as the sole nitrogen source is demonstrated. This strategy works smoothly under air atmosphere, and affords symmetrical 2,4,6-trisubstituted and unsymmetrical 1,3,5-triazines with yields from 18% to 72%. Compared to other methods, the present protocol provides a straightforward and atom-efficient approach to 2,4,6-trisubstituted 1,3,5-triazines using an inexpensive, easily available ammonium salt as the sole nitrogen source. Research into the preliminary mechanism indicates that -benzylidenebenzimidamides are involved in this cyclization reaction.

摘要

展示了一种原子经济、直接的方法来合成2,4,6-三芳基-1,3,5-三嗪,即通过铁催化醛与NHI作为唯一氮源的环化反应。该策略在空气气氛下顺利进行,可得到对称的2,4,6-三取代和不对称的1,3,5-三嗪,产率为18%至72%。与其他方法相比,本方案使用廉价、易得的铵盐作为唯一氮源,为合成2,4,6-三取代1,3,5-三嗪提供了一种直接且原子经济的方法。初步机理研究表明,-亚苄基苯并咪唑酰胺参与了该环化反应。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c40d/9054497/b1e24bf44d86/d0ra03323e-s1.jpg

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