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Volumn 12, Issue 8, 2010, Pages 1397-1404

Metal-free tandem reaction in water: An efficient and regioselective synthesis of 3-hydroxyisoindolin-1-ones

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EID: 77955179915     PISSN: 14639262     EISSN: 14639270     Source Type: Journal    
DOI: 10.1039/c004745g     Document Type: Article
Times cited : (55)

References (37)
  • 9
    • 0003744531 scopus 로고
    • 101, 54922
    • Chem. Abstr., 1984, 101, 54922.
    • (1984) Chem. Abstr.
  • 28
    • 85032779783 scopus 로고    scopus 로고
    • 13C NMR and mass spectroscopy of 9Aa are in the Experimental Section; see ESI for crystal structure data
    • 13C NMR and mass spectroscopy of 9Aa are in the Experimental Section; see ESI for crystal structure data.
  • 29
    • 85032755604 scopus 로고    scopus 로고
    • The gram-scale target product could be also purified by using recrystallisation with ethyl acetate and petroleum ether
    • The gram-scale target product could be also purified by using recrystallisation with ethyl acetate and petroleum ether.
  • 32
    • 85032757632 scopus 로고    scopus 로고
    • A solution of 9Aa (0.5 mmol) in 6 N hydrochloric acid solution (2 mL) and methanol (20 mL) was stirred at room temperature for 4 h. The solvent was removed under reduced pressure, and the residue was purified by flash chromatography (eluent: petroleum ether–ethyl acetate = 25: 1, v/v) to product (E)-11 and (Z)-11, respectively (see the ESI for details)
    • A solution of 9Aa (0.5 mmol) in 6 N hydrochloric acid solution (2 mL) and methanol (20 mL) was stirred at room temperature for 4 h. The solvent was removed under reduced pressure, and the residue was purified by flash chromatography (eluent: petroleum ether–ethyl acetate = 25: 1, v/v) to product (E)-11 and (Z)-11, respectively (see the ESI for details).
  • 37
    • 85032764853 scopus 로고    scopus 로고
    • To further explore the proposed mechanism, we attempted to synthesize one of the intermediates (M1) from Scheme 4 as the starting material for this catalytic cycle, and found that the same good yield (95%) of the target product (9Aa) was obtained under the optimum reaction conditions (see the ESI for details of intermediate M1)
    • To further explore the proposed mechanism, we attempted to synthesize one of the intermediates (M1) from Scheme 4 as the starting material for this catalytic cycle, and found that the same good yield (95%) of the target product (9Aa) was obtained under the optimum reaction conditions (see the ESI for details of intermediate M1).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.