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富氮多孔有机聚合物在球磨固相合成 2-氨基-4H-苯并[b]吡喃骨架中的应用。

Application of nitrogen-rich porous organic polymer for the solid-phase synthesis of 2-amino-4H-benzo[b]pyran scaffolds using ball milling process.

机构信息

Nanotechnology and Catalysis Research Center, Institute of Postgraduate Studies, University of Malaya, 50603, Kuala Lumpur, Malaysia.

Environmental Research Laboratory, Department of Water and Environmental Engineering, School of Civil Engineering, Iran University of Science and Technology, 16765-163, Tehran, Iran.

出版信息

Mol Divers. 2021 Feb;25(1):323-332. doi: 10.1007/s11030-020-10092-4. Epub 2020 May 2.

Abstract

This paper presents the efficient synthesis of 2-amino-4H-benzo[b]pyrans using mesoporous poly-melamine-formaldehyde as a polymeric heterogeneous catalyst. According to the principals of green chemistry, the reaction was performed by the planetary ball milling process at ambient and neat conditions. The heterogeneous catalyst could be reused up to five runs with no reducing of catalytic efficiency. A variety of substituted 2-amino-4H-benzo[b]pyrans were obtained in good to excellent yields under eco-friendly conditions. Other advantages of the current methodology include short reaction time, wide substrate-scope, and use of a metal-free polymeric catalyst. Also, the current method avoids the use of hazardous reagents and solvents, tedious workup and multi-step purification. This work revealed that porous organic polymers containing Lewis base sites having acceptor-donner hydrogen bonding functional groups, and high porosity could play a vital role in the promotion of the one-pot multicomponent reactions in the solid-phase synthesis.

摘要

本文提出了一种使用介孔聚三聚氰胺-甲醛作为聚合多相催化剂高效合成 2-氨基-4H-苯并[b]吡喃的方法。根据绿色化学原理,在环境和纯条件下通过行星球磨法进行反应。多相催化剂在没有降低催化效率的情况下可以重复使用五倍。在环保条件下,通过该方法可以获得各种取代的 2-氨基-4H-苯并[b]吡喃,产率良好至优秀。当前方法的其他优点包括反应时间短、底物范围广、使用无金属的聚合物催化剂。此外,当前方法避免了使用危险试剂和溶剂、繁琐的后处理和多步纯化。这项工作表明,含有路易斯碱位、具有给体-受体氢键官能团和高孔隙率的多孔有机聚合物可以在促进多组分反应的固相合成中发挥重要作用。

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