Thiazole formation via traceless cleavage of Rink resin

Tetrahedron Letters

Volumn 41, Issue 25, 2000, Pages 4965-4968

  Pons, Jean François ^a   Mishir, Qayum ^a   Nouvet, André ^a   Brookfield, Frederick ^a  

^a Oxford Asymmetry International   (United Kingdom)

Author keywords

Lawesson's reagent; Rink amide resin; Thiazole; Traceless; haloketones

Indexed keywords

HALOKETONE; RESIN; THIAZOLE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; SYNTHESIS;

EID: 0034686260     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00748-6     Document Type: Article

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14. -1) of resin bound amide was suspended in 30 ml of THF. Lawesson's reagent (1.5 g, 3.7 mmol, 3 equiv.) was then added and the reaction mixture heated at reflux for 4 h (monitoring by IR). The resin was washed with (DMF×3, DCM×3 and tert-butylmethyl ether×3)×3. Thiazole forming cleavage: 300 mg of resin bound thioamide was suspended in 5 ml of THF. 3-Nitrophenacyl bromide (44 mg, 0.18 mmol, 0.6 equiv.) was added and the reaction mixture heated at reflux for 16 h.