Microwave-Assisted Synthesis of 2-Substituted 2-Thiazolines and 5,6-Dihydro-4 H -1,3-thiazines

被引：5

作者：

Mollo, Maria C. ^{[1
]}

Bisceglia, Juan A. ^{[1
]}

Kilimciler, Natalia B. ^{[1
]}

Mancinelli, Michele ^{[2
]}

Orell, Liliana R. ^{[1
]}

机构：

[1] Univ Buenos Aires, CONICET, Dept Quim Organ, Fac Farm & Bioquim, Junin 956, RA-1113 Buenos Aires, DF, Argentina

[2] Univ Bologna, Dept Ind Chem Toso Montanari, Viale Risorgimento 4, I-40136 Bologna, Italy

来源：

SYNTHESIS-STUTTGART | 2020年 / 52卷 / 11期

关键词：

cyclic iminothioethers; thiazolines; dihydrothiazines; PPE; microwaves; thioamidoalcohols; EFFICIENT HOMOGENEOUS CATALYST; BETA-HYDROXY THIOAMIDES; LAWESSONS REAGENT; FACILE SYNTHESIS; MEDIATED CYCLODEHYDRATION; AMINO-ALCOHOLS; THIAZOLINES; STRAIGHTFORWARD; LIGANDS; 2-OXAZOLINES;

D O I：

10.1055/s-0039-1690822

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient and general method for the synthesis of 2-substituted thiazolines and 5,6-dihydro-4 H -1,3-thiazines is developed via microwave-assisted ring closure of omega -thioamidoalcohols promoted by ethyl polyphosphate (PPE). The cyclization reaction involves an S (N) 2-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 omega -aminoalcohols. The whole process is metal-free and operationally simple.

引用

页码：1666 / 1679

页数：14

共 86 条

[1] Synthesis of new chiral thiazoline-containing ligands [J].