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Cyclization Reactions Involving 2-Aminoarenetellurols and Derivatives of α,β-Unsaturated Carboxylic Acids
Heteroatom Chemistry ( IF 0.3 ) Pub Date : 2021-12-22 , DOI: 10.1155/2021/7140222
Jayna A. Patel 1 , Aundrea M. Lee 1 , Donna V. Franklin 1 , Frank R. Fronczek 2 , Thomas Junk 1
Affiliation  

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.

中文翻译:

涉及 2-氨基芳烃四醇和 α,β-不饱和羧酸衍生物的环化反应

载有α , β的芳烃的还原环化研究了邻位的-不饱和酰胺官能团。从概念上讲,这些化合物可以形成 1,3-碲氮唑而不涉及环闭合中的不饱和度,它们可以形成 1,4-碲嗪酮衍生物,或者它们可以进行环闭合形成 1,5-碲氮酮。来自丙烯酸和甲基丙烯酸的酰胺生成 1,5-碲氮酮,而 2-肉桂酰氨基苯碲醇环化为 1,3-碲唑衍生物。相比之下,乙炔二羧酸及其衍生物与 2-氨基芳烃四烯酮的反应生成了 1,4-碲氮酮,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-氨基芳烃四醇获得的产物的良好预测因子。选定的化合物通过 X 射线晶体学表征。目前的工作提供了对以前未探索过的有机碲杂环的访问。
更新日期:2021-12-22
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