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Volumn , Issue 19, 2007, Pages 2999-3002

A new general synthesis of N-hydroxyindoles

Author keywords

Catalytic hydrogenation; N hydroxyindoles; N methoxyindoles; Reductive cyclization; Tetrakis(triphenylphosphine)palladium

Indexed keywords

1 HYDROXYINDOLE DERIVATIVE; 2 NITROBENZYL ALDEHYDE DERIVATIVE; ALDEHYDE DERIVATIVE; AMIDE; INDOLE DERIVATIVE; KETONE; PALLADIUM; TETRAKIS(TRIPHENYLPHOSPHINE)PALLADIUM; UNCLASSIFIED DRUG;

EID: 37249059275     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-990970     Document Type: Article
Times cited : (13)

References (29)
  • 7
    • 0036096658 scopus 로고    scopus 로고
    • For reviews on N-hydroxyindoles, see: (a) Somei, M. Adv. Heterocycl. Chem. 2002, 82, 101.
    • For reviews on N-hydroxyindoles, see: (a) Somei, M. Adv. Heterocycl. Chem. 2002, 82, 101.
  • 24
    • 37249091388 scopus 로고    scopus 로고
    • Most of the substrates used for the reductive cyclization were prepared by aromatic electrophilic substitution, either with NaH in DMF15 (1a-c, 4 and 9c) or NaOH/TBAHS/ toluene18 9a,b, Compounds 11a-c, 14 and 17 were commercially available and 20 was prepared via a Pd-catalyzed arylation of a ketone enolate.9
    • 9
  • 28
    • 37249006957 scopus 로고    scopus 로고
    • Typical Experimental Procedures: 2-tert-Butyl-1- hydroxy-6-(trifluoromethyl)-1H-indole-3-carbonitrile (10b, To a solution of 4,4-dimethyl-2-[2-nitro-4-(trifluoromethyl)phenyl]-3- oxopentanenitrile (9b; 236 mg, 0.75 mmol) in a mixture of EtOAc and AcOH (4:1, 12 mL) were added 10% Pd/C (40 mg, 0.05 equiv) and (Ph3P) 4Pd (13 mg, 0.015 equiv, This mixture was degassed and stirred under an atmosphere of hydrogen for 4 h. The solids were removed by a filtration through Celite and the solvents were evaporated. Flash chromatography of the residue on silica gel using a gradient of EtOAc-hexane (0-25, as eluent afforded 10b (204 mg, 96% yield) as a light beige powder; mp 144°C (dec, 1H NMR (400 MHz, acetone-d6, δ, 11.07 (s, 1 H, 7.84 (s, 1 H, 7.81 (d, J, 8.3 Hz, 1 H, 7.58 (dd, J, 1.3, 8.3 Hz, 1 H, 1.69 (s, 9 H, 13C NMR 100 MHz, acetone-d
    • 4: C, 53.00; H, 4.45; N, 4.41. Found: C, 53.20; H, 4.13; N, 4.30.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.