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可持续的三嗪基脱氢缩合剂用于酰胺合成。

Sustainable Triazine-Based Dehydro-Condensation Agents for Amide Synthesis.

机构信息

Dipartimento di Scienze Molecolari e Nanosistemi, Università Ca' Foscari di Venezia, Via Torino 155, 30172 Venezia, Italy.

Crossing srl, Viale della Repubblica 193/b, 31100 Treviso, Italy.

出版信息

Molecules. 2021 Jan 2;26(1):191. doi: 10.3390/molecules26010191.

DOI:10.3390/molecules26010191
PMID:33401732
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC7795458/
Abstract

Conventional methods employed today for the synthesis of amides often lack of economic and environmental sustainability. Triazine-derived quaternary ammonium salts, e.g., 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMTMM(Cl)), emerged as promising dehydro-condensation agents for amide synthesis, although suffering of limited stability and high costs. In the present work, a simple protocol for the synthesis of amides mediated by 2-chloro-4,6-dimethoxy-1,3,5-triazine (CDMT) and a -amine has been described and data are compared to DMTMM(Cl) and other CDMT-derived quaternary ammonium salts (DMT-Ams(X), X: Cl or ClO). Different -amines (Ams) were tested for the synthesis of various DMT-Ams(Cl), but only DMTMM(Cl) could be isolated and employed for dehydro-condensation reactions, while all CDMT/-amine systems tested were efficient as dehydro-condensation agents. Interestingly, in best reaction conditions, CDMT and 1,4-dimethylpiperazine gave -phenethyl benzamide in 93% yield in 15 min, with up to half the amount of -amine consumption. The efficiency of CDMT/-amine was further compared to more stable triazine quaternary ammonium salts having a perchlorate counter anion (DMT-Ams(ClO)). Overall CDMT/-amine systems appear to be a viable and more economical alternative to most dehydro-condensation agents employed today.

摘要

今天用于酰胺合成的常规方法往往缺乏经济性和环境可持续性。三嗪衍生的季铵盐，例如 4-(4,6-二甲氧基-1,3,5-三嗪-2-基)-4-甲基吗啉氯化物(DMTMM(Cl))，作为酰胺合成的有前途的脱氢缩合试剂出现，尽管其稳定性有限且成本高。在本工作中，描述了一种由 2-氯-4,6-二甲氧基-1,3,5-三嗪(CDMT)和 -胺介导的酰胺合成的简单方法，并将数据与 DMTMM(Cl)和其他 CDMT 衍生的季铵盐(DMT-Ams(X)，X: Cl 或 ClO)进行了比较。不同的 -胺(Ams)被用于合成各种 DMT-Ams(Cl)，但只有 DMTMM(Cl)可以被分离并用于脱氢缩合反应，而所有测试的 CDMT/-胺系统都作为脱氢缩合试剂有效。有趣的是，在最佳反应条件下，CDMT 和 1,4-二甲基哌嗪在 15 分钟内以 93%的产率得到 -苯乙基苯甲酰胺，-胺的消耗减少了一半。CDMT/-胺的效率进一步与具有高氯酸盐阴离子(DMT-Ams(ClO))的更稳定的三嗪季铵盐进行了比较。总体而言，CDMT/-胺系统似乎是当今使用的大多数脱氢缩合试剂的可行且更经济的替代方案。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9327/7795458/4a8aa5ccc893/molecules-26-00191-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9327/7795458/393056ccd004/molecules-26-00191-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9327/7795458/3e2678e184ae/molecules-26-00191-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9327/7795458/a4ec9c84327d/molecules-26-00191-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9327/7795458/b074d7ffba24/molecules-26-00191-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9327/7795458/e3cb9be16a3c/molecules-26-00191-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9327/7795458/9662a64e0a36/molecules-26-00191-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9327/7795458/1b37d43ebd8e/molecules-26-00191-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9327/7795458/4a8aa5ccc893/molecules-26-00191-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9327/7795458/393056ccd004/molecules-26-00191-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9327/7795458/3e2678e184ae/molecules-26-00191-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9327/7795458/a4ec9c84327d/molecules-26-00191-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9327/7795458/b074d7ffba24/molecules-26-00191-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9327/7795458/e3cb9be16a3c/molecules-26-00191-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9327/7795458/9662a64e0a36/molecules-26-00191-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9327/7795458/1b37d43ebd8e/molecules-26-00191-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9327/7795458/4a8aa5ccc893/molecules-26-00191-g005.jpg

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