Traceless solid-phase synthesis of 2-amino-5-alkylidene-thiazol-4-ones

Tetrahedron Letters

Volumn 46, Issue 14, 2005, Pages 2387-2391

  Pulici, Maurizio ^a   Quartieri, Francesca ^a  

^a NERVIANO MEDICAL SCIENCES   (Italy)

Author keywords

Knovenagel reaction; Solid phase synthesis; Thiazolone; Traceless linker

Indexed keywords

ALDEHYDE; AMINE; RESIN; RHODANINE; THIAZOLE DERIVATIVE;

ARTICLE; CHEMICAL REACTION KINETICS; DRUG SYNTHESIS; POLYMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; SOLID PHASE SYNTHESIS; TEMPERATURE DEPENDENCE;

EID: 17744379987     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.02.059     Document Type: Article

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33. 3 and NaOH. Typical loading procedure: To a suspension of bromo-Wang resin (1 g, declared loading 1.4 mmol/g) in DMF (15 mL), rhodanine (652 mg, 3.5 equiv) is added followed by DIEA (500 μL, 362 mg, 2 equiv). The mixture is gently shaken for 40 h. The resin is filtered, washed with DMF, MeOH, DCM, and dried in vacuo. Obtained 1.058 g (calculated loading 1.092 mmol/g, theoretical loading 1.303 mmol/g, 83%)
34. The resin obtained as reported in Ref. 15 (150 mg, 0.1638 mmol) was treated with excess piperidine (150 μL, 9.3 equiv) in DME-TFE (9:1) at 70°C for 3 h. The product was then isolated by silica gel chromatography (DCM-MeOH 98:2): 24.7 mg (0.134 mmol, 82 %). No further product was recovered on reiteration
35. 3) δ ppm 35.8, 48.0, 128.4, 128.9, 129.5, 135.2, 174.0, 201.3. In addition only 2a (and not 3a) reacts completely with pyrrolidine (DME-TFE 9:1, 70°C, 1 h) according to the scheme of Ref. 16
36. Compounds with this general structure are known: K.A. Kandeel, A.M. Youssef, H.M. El-Bestawy, and M.T. Omar J. Chem. Res. Synop. 2003 682
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38. Calculation of the H-C coupling constant is in good agreement with this stereochemistry:
39. The whole synthetic sequence has been carried out using either vials, Argonaut Quest 210, or Bohdan Miniblocks. Typical procedure for the 2-amino-5-alkylidene-thiazol-4-ones synthesis: 150 mg of the resin obtained as reported in Ref. 15 was suspended in DCM (3 mL) and the aldehyde (100 mg or μL) was added. Next DIEA (100 μL) was added and the mixture gently shaken for 40 h. The resin was washed successively with DMF, MeOH, and DCM (three times each). The resin was then slurried in DME-TFE (9:1) and treated with the amine (100 mg or μL) and heated at 70°C for 6 h. The cleaved material was then isolated and the resin rinsed once with DCM-MeOH (9:1). Solvent was removed in vacuo yielding the reaction crude that was purified as mentioned in the text