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A one-pot four-component synthesis of 3-[(2-amino-4-arylthiazolium-5-yl)(aryl)methyl]-2-oxo-2H-1-benzopyran-4-olates
Journal of Sulfur Chemistry ( IF 2.1 ) Pub Date : 2020-06-04 , DOI: 10.1080/17415993.2020.1774592
Hosna Sayadian 1 , Issa Yavari 2 , Mohammad Reza Halvagar 3
Affiliation  

ABSTRACT An efficient method has been developed for the synthesis of 3-[(2-amino-4-arylthiazolium-5-yl)(aryl)methyl]-2-oxo-2H-1-benzopyran-4-olates via a tandem reaction involving 4-hydroxycoumarin, benzaldehydes, thiourea, and 2-bromo-1-arylethan-1-ones, using p-toluenesulfonic acid as catalyst in glacial acetic acid under reflux. The identity of the parent product was confirmed by X-ray analyses while the other similar derivatives were identified by NMR. The good yields of the products, regioselectivity, and lack of metal promoters are the main advantages of this protocol. Highlights The reaction of 4-hydroxycoumarin, thiourea, benzaldehydes, and 2-bromo-1-arylethan-1-ones leads to the formation of functionalized 3-[(2-amino-4-arylthiazolium-5-yl)(aryl)methyl]-2-oxo-2H-1-benzopyran-4-olates in good yields. GRAPHICAL ABSTRACT

中文翻译:

一锅四组分合成 3-[(2-amino-4-arylthiazolium-5-yl)(aryl)methyl]-2-oxo-2H-1-benzopyran-4-olates

摘要 开发了一种通过串联反应合成 3-[(2-amino-4-arylthiazolium-5-yl)(aryl)methyl]-2-oxo-2H-1-benzopyran-4-olates 的有效方法涉及4-羟基香豆素、苯甲醛、硫脲和2-溴-1-芳基-1-酮,使用对甲苯磺酸作为催化剂,在冰醋酸中回流。通过 X 射线分析确认了母体产品的身份,而通过 NMR 确定了其他类似的衍生物。产品的良好产量、区域选择性和缺乏金属促进剂是该协议的主要优点。亮点 4-羟基香豆素、硫脲、苯甲醛和 2-bromo-1-arylethan-1-ones 的反应导致形成功能化的 3-[(2-amino-4-arylthiazolium-5-yl)(aryl)methyl ]-2-oxo-2H-1-benzopyran-4-olates 收率良好。图形概要
更新日期:2020-06-04
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