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Synlett
Volumn , Issue 10, 2007, Pages 1529-1532
Thia-Michael addition using cheap and odorless S-alkylisothiouronium salts as thiol equivalents in water
Author keywords

Electron deficient olefins; Green chemistry; S alkylisothio uronium salts; Thia Michael addition; Thiol equivalent
Indexed keywords

ALKYL GROUP; ISOTHIURONIUM DERIVATIVE; THIOL DERIVATIVE; UNCLASSIFIED DRUG; WATER;
EID: 34347351356     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-982530     Document Type: Article
Times cited : (32)
References (58)
  • 1
    • 0004188696 scopus 로고    scopus 로고
    • Vols, Page, P. C. B, Ed, Springer: Berlin
    • (a) Organosulfur Chemistry. Vols. 1-2; Page, P. C. B., Ed.; Springer: Berlin, 1999.
    • (1999) Organosulfur Chemistry , pp. 1-2
  • 57
    • 34347347792 scopus 로고    scopus 로고
    • Typical Procedure for the Thia-Michael Addition of S-Alkylisothiouronium Salts to Electron-Deficient Olefins: To a magnetically stirred solution of an S-alkylisothio-uronium salt (3 mmol) and an electron-deficient olefin (3 mmol) in H2O (5 mL) was slowly added an aq NaOH solution (7.5 mmol NaOH in 2 mL H2O, and then the mixture was stirred at r.t. for the indicated time in Table 1. Then, the reaction mixture was extracted with EtOAc 3 x 10 mL, The combined organic extracts were dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography over silica gel using EtOAc-PE as eluent to afford the corresponding product. All the new compounds were characterized on the basis of 1H NMR and elemental analysis and the structures of the known compounds were confirmed by 1H NMR spectra, which were consistent with literature data
    • 1H NMR spectra, which were consistent with literature data.
  • 58
    • 34347346777 scopus 로고    scopus 로고
    • Spectroscopic data of the selected compound: 3- Methylthiopropanenitrile14 (3j; Table 1, entry 10, colorless liquid. 1H NMR (300 MHz, CDCl3, δ, 2.20 (s, 3 H, 2.67 (t, J, 6.9 Hz, 2 H, 2.78 (t, J, 6.9 Hz, 2 H, 3-Cyclopentylthiopropanenitrile (3u; Table 1, entry 21, colorless liquid. 1H NMR (300 MHz, CDCl3, δ, 148-1.62 (m, 4 H, 1.73-1.77 (m, 2 H, 1.97-2.05 (m, 2 H, 2.64 (t, J, 7.2 Hz, 2 H, 2.81 (t, J, 7.2 Hz, 2 H, 3.13-3.23 (m, 1 H, Anal. Calcd for C 8H13NS: C, 61.89; H, 8.44; N, 9.02. Found: C, 61.92; H, 8.274; N, 8.902. 3-Phenyl-3-benzylthiopropanenitrile (3v; Table 1; entry 22, colorless oil. 1H NMR (300 MHz, CDCl3, δ, 2.80 (dd, J, 2.5, 7.5 Hz, 2 H, 3.52 (d, J, 13.8 Hz, 3.66 (d, J, 13.8 Hz, 1 H, 3.90 (t, J, 7.2 Hz, 1 H, 7.21-741 m, 10 H, Anal. Calcd for C16
    • 15NS: C, 75.8; H, 5.91; N, 5.53. Found: C, 75.70; H, 6.04; N, 5.41.

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.