Synthesis of 2,2-difluoro-2-arylethylamines as fluorinated analogs of octopamine and noradrenaline

IF 1.3 3区 化学 Q3 CHEMISTRY, ORGANIC Heterocyclic Communications Pub Date : 2022-01-01 DOI:10.1515/hc-2022-0005
A. Tarui, Erika Kamata, Koji Ebisu, Y. Kawai, Ryota Araki, Takeshi Yabe, Yukiko Karuo, Kazuyuki Sato, Kentaro Kawai, M. Omote
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Abstract

Abstrtact A series of 2,2-difluoro-2-arylethylamines was synthesized as fluorinated analogs of octopamine and noradrenaline with the expectation of bioisosteric OH/F exchanges. The syntheses of these compounds were performed by a Suzuki–Miyaura cross-coupling reaction of 4-(bromodifluoroacetyl)morpholine with aryl boronic acids to produce the intermediate 2,2-difluoro-2-arylacetamides, followed by transformation of difluoroacetamide to difluoroethylamine.
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作为章鱼胺和去甲肾上腺素氟化类似物的2,2-二氟-2-芳基乙胺的合成
摘要合成了一系列的2,2-二氟-2-芳基乙胺,作为章鱼胺和去甲肾上腺素的氟化类似物,期望能进行生物等构的OH/F交换。这些化合物是通过4-(溴代氟乙酰基)啉与芳基硼酸的Suzuki-Miyaura交叉偶联反应合成的,得到中间体2,2-二氟-2-芳基乙酰胺,然后将二氟乙酰胺转化为二氟乙胺。
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来源期刊
Heterocyclic Communications
Heterocyclic Communications 化学-有机化学
CiteScore
3.80
自引率
4.30%
发文量
13
审稿时长
1.4 months
期刊介绍: Heterocyclic Communications (HC) is a bimonthly, peer-reviewed journal publishing preliminary communications, research articles, and reviews on significant developments in all phases of heterocyclic chemistry, including general synthesis, natural products, computational analysis, considerable biological activity and inorganic ring systems. Clear presentation of experimental and computational data is strongly emphasized. Heterocyclic chemistry is a rapidly growing field. By some estimates original research papers in heterocyclic chemistry have increased to more than 60% of the current organic chemistry literature published. This explosive growth is even greater when considering heterocyclic research published in materials science, physical, biophysical, analytical, bioorganic, pharmaceutical, medicinal and natural products journals. There is a need, therefore, for a journal dedicated explicitly to heterocyclic chemistry and the properties of heterocyclic compounds.
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