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Synthesis 2020; 52(11): 1666-1679
DOI: 10.1055/s-0039-1690822
DOI: 10.1055/s-0039-1690822
paper
Microwave-Assisted Synthesis of 2-Substituted 2-Thiazolines and 5,6-Dihydro-4H-1,3-thiazines
This work was supported by the University of Buenos Aires (Grant No. 20020170100189BA).Further Information
Publication History
Received: 28 December 2019
Accepted after revision: 23 January 2020
Publication Date:
24 February 2020 (online)
Abstract
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.
Key words
cyclic iminothioethers - thiazolines - dihydrothiazines - PPE - microwaves - thioamidoalcoholsSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0039-1690822.
- Supporting Information
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