First synthesis of 2-aminosubstituted-2-perfluoroalkyl-3,6-dihydro-2H-thiopyrans by hetero-Diels-Alder reactions of fluorinated thioamides under microwave heating

Tetrahedron Letters

Volumn 51, Issue 6, 2010, Pages 990-993

  Mikhailichenko, Sergey S ^a,b   Bouillon, Jean Philippe ^a   Besson, Thierry ^c   Shermolovich, Yuri G ^b  

^a UNIVERSITÉ DE ROUEN   (France)

^b INSTITUTE OF ORGANIC CHEMISTRY   (Ukraine)

^c INSA   (France)

Author keywords

2H Thiopyran; Fluorine; Hetero Diels Alder reaction; Microwaves; Sulfur; Thioamide

Indexed keywords

THIOPYRAN DERIVATIVE; TRIFLUOROMETHANESULFONIC ACID;

ARTICLE; CHEMICAL ANALYSIS; CYCLOADDITION; DIELS ALDER REACTION; MICROWAVE RADIATION;

ALNUS;

EID: 73249134640     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.12.064     Document Type: Article

References (29)

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23. 4, filtered, and evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel, eluting with a mixture (9:1) of petroleum ether and ethyl acetate affording 121 mg (yield: 43%) of cycloadduct 2a (Scheme 3, Table 2).
24. 3KNOS m/z 320.0698, found 320.0692.
25. Typical procedure for the preparation of ammonium salt 3a: a mixture of compound 2a (1.0 mmol) and trifluoromethanesulfonic acid (1.0 mmol) in n-hexane (15 mL) was stirred for 16 h at room temperature. After completion of the reaction, the solution was decanted and the product was dried in vacuo affording 0.40 g (yield: 92%) of ammonium salt 3a (Scheme 4).
26. 2: C, 36.19; H, 4.44; N, 3.25; S, 14.87. Found: C, 35.94; H, 4.65; N, 3.38; S, 17.92.
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