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Microwave-Assisted Synthesis of 2-Substituted 2-Thiazolines and 5,6-Dihydro-4H-1,3-thiazines
Synthesis ( IF 2.2 ) Pub Date : 2020-02-24 , DOI: 10.1055/s-0039-1690822 Liliana R. Orelli 1 , María C. Mollo 1 , Juan A. Bisceglia 1 , Natalia B. Kilimciler 1 , Michele Mancinelli 2
Synthesis ( IF 2.2 ) Pub Date : 2020-02-24 , DOI: 10.1055/s-0039-1690822 Liliana R. Orelli 1 , María C. Mollo 1 , Juan A. Bisceglia 1 , Natalia B. Kilimciler 1 , Michele Mancinelli 2
Affiliation
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An efficient and general method for the synthesis of 2-substituted thiazolines and 5,6-dihydro-4H-1,3-thiazines is developed via microwave-assisted ring closure of ω-thioamidoalcohols promoted by ethyl polyphosphate (PPE). The cyclization reaction involves an SN2-type mechanism and features the advantages of very short reaction times, high yields and a predictable stereochemical outcome. The acyclic precursors are prepared in high overall yields by an improved diacylation–thionation–saponification sequence from commercially available ω-aminoalcohols. The whole process is metal-free and operationally simple.
中文翻译：
微波辅助合成2-取代的2-噻唑啉和5,6-二氢-4H-1,3-噻嗪
通过微波辅助聚磷酸乙酯（PPE）促进的ω-硫代酰胺醇的闭环反应，开发了一种高效且通用的合成2-取代的噻唑啉和5,6-二氢-4 H -1,3-噻嗪的方法。环化反应涉及S N 2型机理，具有反应时间短，产率高和可预测的立体化学结果的优点。无环前体是通过改进的二酰化-硫磺化-皂化顺序，从市售的ω-氨基醇中以高收率制备的。整个过程无金属且操作简单。
更新日期：2020-04-21
中文翻译：
微波辅助合成2-取代的2-噻唑啉和5,6-二氢-4H-1,3-噻嗪
通过微波辅助聚磷酸乙酯（PPE）促进的ω-硫代酰胺醇的闭环反应，开发了一种高效且通用的合成2-取代的噻唑啉和5,6-二氢-4 H -1,3-噻嗪的方法。环化反应涉及S N 2型机理，具有反应时间短，产率高和可预测的立体化学结果的优点。无环前体是通过改进的二酰化-硫磺化-皂化顺序，从市售的ω-氨基醇中以高收率制备的。整个过程无金属且操作简单。
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