A three-component novel synthesis of 1-carbamato-alkyl-2-naphthol derivatives

Tetrahedron Letters

Volumn 49, Issue 40, 2008, Pages 5804-5806

  Shaterian, Hamid Reza ^a   Hosseinian, Asghar ^a   Ghashang, Majid ^a  

^a UNIVERSITY OF SISTAN AND BALUCHESTAN   (Iran)

Author keywords

1 Carbamato alkyl 2 naphthol; Carbamates; Heterogeneous catalyst; Multi component reaction; SiO2 NaHSO4

Indexed keywords

1 AMINOMETHYL 2 NAPHTHOL DERIVATIVE; 2 NAPHTHOL; BENZALDEHYDE DERIVATIVE; BISULFATE; BISULFITE; CARBAMIC ACID DERIVATIVE; NAPHTHOL DERIVATIVE; SILICON DIOXIDE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; ONE POT SYNTHESIS; POLYMERIZATION;

EID: 49549123799     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.07.126     Document Type: Article

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35. 18 All yields refer to isolated products after purification.
36. General procedure for the preparation of 1-carbamato-alkyl-2-naphthol derivatives: To a mixture of 2-naphthol (1 mmol), aldehyde (1 mmol), and methyl/benzyl carbamate (1.2 mmol), silica supported sodium hydrogen sulfate (0.05 g) was added. The mixture was stirred at 100 °C in an oil bath and the reaction was followed by TLC. After completion, the mixture was cooled to room temperature, and then ethanol was added to dissolve the precipitated product. The catalyst was filtered and the filtrate evaporated. Then, the solid product was purified by recrystallization from aqueous EtOH (20%). Spectral data are given below.
37. 3: C, 74.25; H, 5.58; N, 4.56%. Found: C, 74.23; H, 5.57; N, 4.52%.
38. 5: C, 64.77; H, 4.58; N, 7.95%. Found: C, 64.75; H, 4.58; N, 7.91%.
39. 3: C, 66.77; H, 4.72; N, 4.10%. Found: C, 66.71; H, 4.68; N, 4.10%.
40. 3: C, 60.65; H, 4.02; N, 3.72%. Found: C, 60.61; H, 4.04; N, 3.75%.
41. 3: C, 66.77; H, 4.72; N, 4.10%. Found: C, 67.02; H, 4.75; N, 4.11%.
42. 5: C, 64.77; H, 4.58; N, 7.95%. Found: C, 64.80; H, 4.57; N, 7.92%.
43. 5: C, 68.65; H, 5.76; N, 3.81%. Found: C, 68.58; H, 5.75; N, 3.83%.
44. 3: C, 78.31; H, 5.52; N, 3.65%. Found: C, 78.25; H, 5.69; N, 3.64%.
45. 3: C, 71.85; H, 4.82; N, 3.35%. Found: C, 71.65; H, 4.77; N, 3.30%.
46. 3: C, 71.85; H, 4.82; N, 3.35%. Found: C, 71.82; H, 4.85; N, 3.33%.
47. 4: C, 75.53; H, 5.61; N, 3.39%. Found: C, 75.45; H, 5.58; N, 3.40%.
48. 3: C, 74.80; H, 5.02; N, 3.49%. Found: C, 74.71; H, 4.97; N, 3.44%.