Cyclization Reactions Involving 2-Aminoarenetellurols and Derivatives of α,β-Unsaturated Carboxylic Acids

IF 1.1 4区化学 Q3 CHEMISTRY, MULTIDISCIPLINARY

Heteroatom Chemistry Pub Date : 2021-12-22 DOI:10.1155/2021/7140222

J. A. Patel, Aundrea M. Lee, D. V. Franklin, F. Fronczek, T. Junk

引用次数: 0

Abstract

The reductive cyclization of arenetellurols carrying α,β-unsaturated amide functionalities in the ortho position was investigated. Conceptually, such compounds can form 1,3-tellurazoles without the involvement of the unsaturation in the ring closure, they can form 1,4-tellurazinone derivatives, or they can undergo ring closure to 1,5-tellurazepinones. Amides derived from acrylic and methacrylic acid generated 1,5-tellurazepinones while 2-cinnamylamidobenzenetellurol cyclized to a 1,3-tellurazole derivative. In contrast, the reaction of acetylenedicarboxylic acid and its derivatives with 2-aminoarenetellurols generated 1,4-tellurazepinones, including a derivative of novel tricyclic naphtho [1, 4]tellurazinone. A comparison with analogous reactions of sulfur congeners indicates that their chemistry is a good predictor for the products obtained from 2-aminoarenetellurols. Selected compounds were characterized by X-ray crystallography. The present work offers access to previously unexplored organotellurium heterocycles.

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2-氨基芳烃四元及α，β-不饱和羧酸衍生物的环化反应

研究了邻位具有α，β-不饱和酰胺官能团的芳烃单元的还原环化反应。从概念上讲，这类化合物可以在不涉及环闭合中的不饱和度的情况下形成1，3-tellurazoles，它们可以形成1，4-tellurazinone衍生物，或者它们可以进行1，5-tellurazepinones的环闭合。由丙烯酸和甲基丙烯酸衍生的酰胺生成1，5-二甲基环戊二烯酮，而2-肉桂酰氨基苯三烯三醇环化生成1，3-三甲基四唑衍生物。相反，乙炔二羧酸及其衍生物与2-氨基芳烃四元醇的反应产生了1，4-碲嗪酮，包括新型三环萘并[1，4]碲嗪酮的衍生物。与硫同系物的类似反应的比较表明，它们的化学性质是从2-氨基芳烃四元醇获得的产物的良好预测指标。用X射线晶体学对所选化合物进行了表征。目前的工作提供了以前未探索的有机碲杂环的途径。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Heteroatom Chemistry 化学-化学综合

CiteScore

1.20

自引率

0.00%

发文量

审稿时长

6 months

期刊介绍： Heteroatom Chemistry brings together a broad, interdisciplinary group of chemists who work with compounds containing main-group elements of groups 13 through 17 of the Periodic Table, and certain other related elements. The fundamental reactivity under investigation should, in all cases, be concentrated about the heteroatoms. It does not matter whether the compounds being studied are acyclic or cyclic; saturated or unsaturated; monomeric, polymeric or solid state in nature; inorganic, organic, or naturally occurring, so long as the heteroatom is playing an essential role. Computational, experimental, and combined studies are equally welcome. Subject areas include (but are by no means limited to): -Reactivity about heteroatoms for accessing new products or synthetic pathways -Unusual valency main-group element compounds and their properties -Highly strained (e.g. bridged) main-group element compounds and their properties -Photochemical or thermal cleavage of heteroatom bonds and the resulting reactivity -Uncommon and structurally interesting heteroatom-containing species (including those containing multiple bonds and catenation) -Stereochemistry of compounds due to the presence of heteroatoms -Neighboring group effects of heteroatoms on the properties of compounds -Main-group element compounds as analogues of transition metal compounds -Variations and new results from established and named reactions (including Wittig, Kabachnik–Fields, Pudovik, Arbuzov, Hirao, and Mitsunobu) -Catalysis and green syntheses enabled by heteroatoms and their chemistry -Applications of compounds where the heteroatom plays a critical role. In addition to original research articles on heteroatom chemistry, the journal welcomes focused review articles that examine the state of the art, identify emerging trends, and suggest future directions for developing fields.