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Synlett
Volumn , Issue 1, 2008, Pages 0129-0133
Unprecedented intramolecular nucleophilic aromatic additions of allyloxy anions to diphenylphosphinoyl-substituted benzene rings: A facile method for preparing multisubstituted benzopyrans
Author keywords

Benzopyrans; Coumarins; Cyclizations; Nucleophilic aromatic additions
Indexed keywords

ANION; BENZENE DERIVATIVE; BENZOPYRAN DERIVATIVE; PEROXIDE;
EID: 38549167390     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-1000835     Document Type: Article
Times cited : (5)
References (28)
  • 19
    • 38549092390 scopus 로고    scopus 로고
    • 2O improved the isomeric ratio to 14:1:1.4 in favor of trans-11 and the yield from 48% to 85%.
    • 2O improved the isomeric ratio to 14:1:1.4 in favor of trans-11 and the yield from 48% to 85%.
  • 20
    • 33845550671 scopus 로고    scopus 로고
    • It is well known that TMSC1 does not react with LDA at -78°C. See: Krizan, T. D.; Martin, J. C. J. Am. Chem. Soc. 1983, 105, 6155.
    • It is well known that TMSC1 does not react with LDA at -78°C. See: Krizan, T. D.; Martin, J. C. J. Am. Chem. Soc. 1983, 105, 6155.
  • 25
    • 38549147349 scopus 로고    scopus 로고
    • 7-Benzyl-6-dimethoxymethyl-3-methyl-4H-chromene (19a, To a solution of allylbenzene 1c (0.61 g, 1.45 mmol) in THF (15 mL) was added a solution LDA over 5 min (1.74 mmol) in THF (6 mL) at -78°C After 4 h at this temperature a solution of benzaldehyde (0.21 g, 2.0 mmol) in THF (3 mL) was added at -78°C over 5 min upon which the dark cherry color disappeared. After 15 min of stirring at this temperature the reaction mixture was allowed to warm to r.t. for 1 h and quenched with aq sat. NH 4Cl solution (5 mL) and H2O (5 mL) under stirring. After 10 min the organic phase was separated and the aqueous one was extracted with CH2Cl2 (2 x 40 mL, The combined organic extract was washed with brine (20 mL, dried over Na2SO4 and concentrated in vacuo. The residue was forwarded to silica gel column chromatography (35 g, hexanes-EtOAc-Et3N, 135:15:1) to give oily 19a 0.28 g, 62
    • 3: 310.1569; found: 310.1546.
  • 26
    • 38549140945 scopus 로고    scopus 로고
    • The moderate yields of this reaction were due to the products being easily oxidized to their corresponding peroxides upon workup
    • The moderate yields of this reaction were due to the products being easily oxidized to their corresponding peroxides upon workup.
  • 27
    • 0037060942 scopus 로고    scopus 로고
    • Compounds with similar structures to 24 have displayed interesting fragrances: Demyttenaere, J.; Van Syngel, K.; Markusse, A. P.; Vervisch, S.; Debenedetti, S.; De Kimpe, N. Tetrahedron 2002, 58, 2163.
    • Compounds with similar structures to 24 have displayed interesting fragrances: Demyttenaere, J.; Van Syngel, K.; Markusse, A. P.; Vervisch, S.; Debenedetti, S.; De Kimpe, N. Tetrahedron 2002, 58, 2163.
  • 28
    • 38549134249 scopus 로고    scopus 로고
    • The peroxides did not survive silica gel purification so they were used immediately in the next reaction. The peroxide was formed in 80-85% yield by 1H NMR spectroscopy
    • 1H NMR spectroscopy).

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.