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Volumn , Issue 12, 2009, Pages 1915-1920

Solvent-free synthesis of alkylthiazolium-based ionic liquids and their use as catalysts in the intramolecular stetter reaction

Author keywords

Ionic liquids; Microwave activation; Solvent free reaction; Stetter reaction; Thiazolium salts

Indexed keywords

4 CHROMANONE DERIVATIVE; ALKYL GROUP; BROMIDE; IODIDE; IONIC LIQUID; THIAZOLE DERIVATIVE; THIAZOLIUM SALT; TRIETHYLAMINE; UNCLASSIFIED DRUG;

EID: 67849100739     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0029-1217518     Document Type: Article
Times cited : (17)

References (59)
  • 1
    • 0347417134 scopus 로고    scopus 로고
    • For selective reviews, see: a
    • For selective reviews, see: (a) Welton, T. Chem. Rev. 1999, 99, 2071.
    • (1999) Chem. Rev , vol.99 , pp. 2071
    • Welton, T.1
  • 5
    • 0012258731 scopus 로고    scopus 로고
    • Ionic Liquids Industrial Applications to Green Chemistry
    • Washington
    • (e) Rogers, R. D.; Seddon, K. R. Ionic Liquids Industrial Applications to Green Chemistry; ACS Symposium Series 818: Washington, 2001.
    • (2001) ACS Symposium Series , vol.818
    • Rogers, R.D.1    Seddon, K.R.2
  • 23
    • 33846895846 scopus 로고    scopus 로고
    • Loupy, A, Ed, Wiley-VCH: Weinheim
    • (f) Microwaves in Organic Synthesis; Loupy, A., Ed.; Wiley-VCH: Weinheim, 2006.
    • (2006) Microwaves in Organic Synthesis
  • 45
    • 0037100146 scopus 로고    scopus 로고
    • For recent reports on the Stetter reaction, see: a
    • For recent reports on the Stetter reaction, see: (a) Raghavan, S.; Anuradha, K. Tetrahedron Lett. 2002, 43, 5181.
    • (2002) Tetrahedron Lett , vol.43 , pp. 5181
    • Raghavan, S.1    Anuradha, K.2
  • 59
    • 67849135472 scopus 로고    scopus 로고
    • General Procedure for the Solvent-Free N-Alkylation of Thiazole under Microwave Irradiation: A mixture of thiazole 1 (85 mg, 1 mmol) and 1-iodoalkane 2 (1.5 mmol) was irradiated (CEM Discover reactor) at 150 °C for the appropriate time (see Table 1, The reaction mixture was brought to room temperature and washed with Et2O (2 x 10 mL, The crude product was dried under reduced pressure to afford a yellow powder which did not need further purification. 1-Butylthiazolium Iodide M.p. 101 °C. 1H NMR (300 MHz, CDCl3, δ, 0.99 (3 H, t, J, 7.5 Hz, 1.40-1.47 (2 H, m, 2.00-2.05 (2 H, m, 4.83 (2 H, t, J, 7.5 Hz, 8.28 (1 H, d, J, 2.6 Hz, 8.34 (1 H, d, J, 3.4 Hz, 10.95 (1 H, s, 13C NMR (75 MHz, CDCl3, δ, 13.9, 19.8, 32.9, 56.5, 127.5, 137.0, 159.6. IR (KBr, 3434, 3020, 2945, 1989, 1829, 1637, 1543, 1434, 1256, 1144, 952, 861, 639 cm-1. HRMS EI, m/z
    • 3): δ = 0.83 (3 H, t, J = 7.1 Hz), 1.28-1.32 (10 H, m), 1.99-2.03 (2 H, m), 4.79 (2 H, t, J = 7.5 Hz), 8.42 (1 H, d, J = 3.4 Hz), 8.52 (1 H, d, J = 3.4 Hz), 10.57 (1 H, s).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.