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Volumn 10, Issue 19, 2008, Pages 4383-4386

Titanocene(III)-catalyzed formation of indolines and azaindolines

Author keywords

[No Author keywords available]

Indexed keywords

HETEROCYCLIC COMPOUND; INDOLE DERIVATIVE; INDOLINE; ORGANOMETALLIC COMPOUND; TITANOCENE;

EID: 55449108912     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol801860s     Document Type: Article
Times cited : (63)

References (41)
  • 3
    • 4143096437 scopus 로고    scopus 로고
    • For indoline preparation using xanthate transfer, see: b, Oxford University Press, Inc, New York
    • For indoline preparation using xanthate transfer, see: (b) Zard, S. Z. In Radical Reactions in Organic Synthesis; Oxford University Press, Inc.: New York, 2003; pp 153-163.
    • (2003) Radical Reactions in Organic Synthesis , pp. 153-163
    • Zard, S.Z.1
  • 12
    • 0002523168 scopus 로고    scopus 로고
    • Renaud, P, Sibi, M. P, Eds, Wiley-VCH: Weinheim
    • (b) Studer, A.; Bossart, M. In Radicals in Organic Synthesis; Renaud, P., Sibi, M. P., Eds.; Wiley-VCH: Weinheim, 2001; Vol. 2, pp 62-76.
    • (2001) Radicals in Organic Synthesis , vol.2 , pp. 62-76
    • Studer, A.1    Bossart, M.2
  • 15
    • 0026737508 scopus 로고    scopus 로고
    • For our previous studies on indoline and isoindolinone synthesis using nucleophilic addition strategies, see: (a) Wipf, P, Kim, Y. Tetrahedron Lett. 1992, 33, 5477
    • For our previous studies on indoline and isoindolinone synthesis using nucleophilic addition strategies, see: (a) Wipf, P.; Kim, Y. Tetrahedron Lett. 1992, 33, 5477.
  • 27
    • 61349192313 scopus 로고    scopus 로고
    • Sonication was used to increase reagent solubility
    • Sonication was used to increase reagent solubility.
  • 28
    • 61349089276 scopus 로고    scopus 로고
    • Typical Procedure: To a flame-dried two-neck flask was added 129 mg (0.43 mmol) of 4c, 3.2 mg (0.01 mmol) of Cp2TiCl 2, 102 mg (0.64 mmol) of collidine hydrochloride, and 35.6 mg (0.64 mmol) of Mn0. The vessel was fitted with a reflux condenser and purged three times with Ar. After addition of 4.3 mL of deoxygenated THF (0.1 M, the reaction mixture was placed in a preheated oil bath and heated at reflux for 3 h. The color of the solution gradually changed from light pink to a dark violet. The mixture was cooled to room temperature, quenched with satd NH 4Cl, extracted with 3 × 10 mL of Et2O, washed with brine, dried (MgSO4, and concentrated in vacuo. The residue was redissolved in 5 mL of MeOH and treated with 30 mg (25% w/w, 0.01 mmol) of Pd/C. The mixture was stirred at room tempearture under 1 atm of H2, and the disappearance of starting material was monitored by TLC hexanes/EtOAc, 1:1
    • 2 (hexanes/EtOAc, 1:2) to afford 44 mg (0.26 mmol, 63%, two steps) of 8c as a yellow oil.
  • 39
    • 61349119424 scopus 로고    scopus 로고
    • 0, the desired Cbz-protected indoline was isolated in only 35% yield.
    • 0, the desired Cbz-protected indoline was isolated in only 35% yield.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.