稳定的三甲酰甲烷合成及其在7-酰基氨基-3-甲酰喹啉合成中的可扩展应用

IF 2.1 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron Pub Date : 2014-04-08 DOI:10.1016/j.tet.2014.02.040

Yasuhiro Sawai, Masahiro Mizuno, Tatsuya Ito, Mitsuhisa Yamano

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引用次数: 6

摘要

新的2-亚甲基甲脒三卤化物作为稳定的晶体被分离出来，并且发现在空气中具有不潮解性质的有用的三甲酰甲烷合子。它们比已知的2-亚甲基二氯化乙烯更容易制造、处理和储存。通过原位胺保护，vinamidinium盐与仲胺的结合实现了7-酰基氨基-3-甲酰喹啉的高效和可扩展合成，这是一种有效的抗肥胖药物7-酰基氨基-3-氨基甲基-8-甲基喹啉的多功能合成中间体。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Synthesis of a stable triformylmethane synthon and its scalable application to 7-acylamino-3-formylquinoline syntheses

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Synthesis of a stable triformylmethane synthon and its scalable application to 7-acylamino-3-formylquinoline syntheses

Novel 2-iminiomethylvinamidinium trihalides were isolated as stable crystals and found to be useful triformylmethane synthons with non-deliquescent nature in air. They were easier to manufacture, handle, and store than the known 2-iminiomethylvinamidinium dichloride. By virtue of in situ aminal protection, a combination of the vinamidinium salt with a secondary amine achieved an efficient and scalable synthesis of 7-acylamino-3-formylquinoline, a versatile synthetic intermediate for potent anti-obesity drugs 7-acylamino-3-aminomethyl-8-methylquinolines.

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来源期刊

Tetrahedron 化学-有机化学

CiteScore

3.90

自引率

4.80%

发文量

439

审稿时长

34 days

期刊介绍： Tetrahedron publishes full accounts of research having outstanding significance in the broad field of organic chemistry and its related disciplines, such as organic materials and bio-organic chemistry. Regular papers in Tetrahedron are expected to represent detailed accounts of an original study having substantially greater scope and details than that found in a communication, as published in Tetrahedron Letters. Tetrahedron also publishes thematic collections of papers as special issues and ''Reports'', commissioned in-depth reviews providing a comprehensive overview of a research area.