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Volumn , Issue 16, 2007, Pages 2549-2552

One-pot tandem 1,4- and 1,2-addition of phosphites to α,β- unsaturated hydrazones

Author keywords

Amino acids; Hydrazones; Michael additions; Phosphorylations; Tandem addition

Indexed keywords

3 PHOSPHONYL 1 HYDRAZINOPHOSPHONATE; HYDRAZONE DERIVATIVE; PHOSPHITE; UNCLASSIFIED DRUG;

EID: 35349030919     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-986654     Document Type: Article
Times cited : (15)

References (18)
  • 1
    • 35349016353 scopus 로고    scopus 로고
    • Diel, P.; Maier, L. EP 143078, 1985; Chem. Abstr. 1985, 103, 215544m.
    • Diel, P.; Maier, L. EP 143078, 1985; Chem. Abstr. 1985, 103, 215544m.
  • 10
    • 33749167216 scopus 로고    scopus 로고
    • Van Meenen, E.; Moonen, K.; Verwée, A.; Stevens, C. V. J Org. Chem. 2006, 71, 7903.
    • Van Meenen, E.; Moonen, K.; Verwée, A.; Stevens, C. V. J Org. Chem. 2006, 71, 7903.
  • 12
    • 35348953795 scopus 로고    scopus 로고
    • The silylated diethyl phosphite was prepared in a separate reaction. Triethylammonium salts were removed from the reagent
    • (b) The silylated diethyl phosphite was prepared in a separate reaction. Triethylammonium salts were removed from the reagent.
  • 15
    • 35348954306 scopus 로고    scopus 로고
    • 31P coupling).
    • 31P coupling).
  • 16
    • 35348977196 scopus 로고    scopus 로고
    • 2-MeOH (81:17:3).
    • 2-MeOH (81:17:3).
  • 18
    • 35348975085 scopus 로고    scopus 로고
    • Detailed Description of the Procedure In an oven-dry flask, hydrazone 2 (2 mmol) is dissolved in abs. EtOH. To this solution, triethyl phosphite (10 mmol, 5 equiv) is added. This mixture is brought to reflux temperature under an N2 atmosphere and formic acid (5 equiv) is added by a syringe. The reaction is followed with 31P NMR. When no changes are observed anymore (after several days) the reaction is stopped. The solvent is evaporated and the residue redissolved in Et2O (20 mL, After pouring into 3 N HCl (30 mL) this system is extracted 3 times with Et 2O (20 mL, The aqueous phase is made basic with 3 N NaOH and extracted three times with CH2Cl2 (20 mL, The combined organic layers are dried over MgSO4. After filtration, the solvent is evaporated in vacuo. 1H NMR, 13C NMR, IR, and MS spectra were entirely consistent with the assigned structures. Selected example:
    • +.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.