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Volumn , Issue 9, 2007, Pages 1452-1454

A novel synthesis of spiro-2,5-dihydro-1,2-λ5- oxaphospholes using a three-component reaction

Author keywords

1,2 oxaphospholes; Isatin; Isopropylacetylenedicarboxylate; Triphenylphosphine

Indexed keywords

ACETYLENEDICARBOXYLIC ACID DIMETHYL ESTER; AMPHOLYTE; DIISOPROPYL 2',2',2' TRIPHENYL 2 OXO SPIRO[1 METHYLINDOLE 3,5' (2',5' DIHYDRO 1',2' LAMBDA5 OXAPHOSPHOLE)] 3',4' DICARBOXYLATE; ISATIN DERIVATIVE; ISOPROPYLACETYLENEDICARBOXYLATE; METISAZONE; ORGANOPHOSPHORUS COMPOUND; SPIRO 1,2 OXAPHOSPHOLE DERIVATIVE; SPIRO 2,5 DIHYDRO 1,2 LAMBDA5 OXAPHOSPHOLE; SPIRO COMPOUND; TRIPHENYLPHOSPHINE; UNCLASSIFIED DRUG;

EID: 34250693677     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-980357     Document Type: Article
Times cited : (17)

References (29)
  • 6
    • 0003397099 scopus 로고
    • Johnson, A. W, Ed, Wiley: New York
    • Ylides and Imines of Phosphorus; Johnson, A. W., Ed.; Wiley: New York, 1993.
    • (1993) Ylides and Imines of Phosphorus
  • 23
    • 34250773101 scopus 로고    scopus 로고
    • Compounds 1-methylisatin (3a, 5-bromo-1-methylisatin (3b, 1-ethylisatin (3c, 5-bromo-1-ethylisatin (3d, 1-benzylisatin (3e) and 1-benzyl-5-bromoisatin (3f) were prepared from alkyl benzensolfonates and the potassium isatin or potassium 5-bromoisatin by known methods.29 Melting points were measured on an Electrothermal 9100 apparatus and are uncorrected. Elemental analyses for C, H and N were performed using a Heraeus CHN-O-Rapid analyzer. IR spectra were measured on a Perkin-Elmer 783 infrared spectrophotometer. 1H, 13C and 31P NMR spectra were measured using a Bruker DRX-250 Avance spectrometer at 500, 125.7 and 202.5 MHz, respectively. Mass spectra were recorded on a Shimadzu GCMS-QP5050 mass spectrometer operating at an ionization potential of 70 eV. Preparation of 1-(morpholinomethyl)isatin (3g, A slurry consisting of the isatin (5 mmol, THF (5 mL) and formalin 2 mL, 37, was made. T
    • 2].
  • 24
    • 34250714098 scopus 로고    scopus 로고
    • General procedure for the synthesis of diisopropyl-2′,2′, 2′-triphenyl-2-oxospiro[1-methylindole-3,5′-(2′, 5′-dihydro-1′,2′-λ5-oxaphosphole, 3′, 4′-dicarboxylate(4a, To a magnetically stirred solution of N-methylisatin (2 mmol) and PPh3 (2 mmol) in CH 2Cl2 (3 mL) was added dropwise, DIAD (2 mmol) at r.t. over 10 min. After 5 h the crude reaction mixture was diluted with CH 2Cl2 and passed through a short plug of silica gel. The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography to give a white powder; mp 177-178°C; IR (KBr, 1720 (N-C=O) 1735, 1740 (2 CO2i-Pr, 1660 (C=C, 1610 (C=Carom, 1430, 1107, 1009 (P-Ph, 1010 (P-O) cm-1; 1H NMR (500 MHz, CDCl3, δ, 0.72 d, J, 6.2 Hz, 3 H, CHMe2
    • 6P: C, 71.49; H, 5.84; N, 2.25. Found: C, 71.00; H, 5.80; N, 2.30.
  • 28
    • 0003656383 scopus 로고
    • Emsley, J, Hall, D, Eds, Harper and Row: London
    • The Chemistry of Phosphorus; Emsley, J.; Hall, D., Eds.; Harper and Row: London, 1976, 82-83.
    • (1976) The Chemistry of Phosphorus , pp. 82-83


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.