메뉴 건너뛰기




Volumn , Issue 6, 2008, Pages 903-912

Palladium-catalyzed synthesis of 3-indolecarboxylic acid derivatives

Author keywords

Catalysis; Cyclizations; Indoles; Palladium; Reductions

Indexed keywords

ALDEHYDES; CARBON MONOXIDE; CATALYSIS; CONDENSATION; CYCLIZATION; NITROBENZENE; PALLADIUM; REDUCTION; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

EID: 41349094803     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1032208     Document Type: Article
Times cited : (50)

References (52)
  • 8
    • 37049081811 scopus 로고    scopus 로고
    • 16 catalysts under CO, see: Crotti, C.; Cenini, S.; Rindone, B.; Tollari, S.; Demartin, F. Chem. Commun. 1986, 784.
    • 16 catalysts under CO, see: Crotti, C.; Cenini, S.; Rindone, B.; Tollari, S.; Demartin, F. Chem. Commun. 1986, 784.
  • 9
  • 10
    • 34547154811 scopus 로고    scopus 로고
    • 3 as oxygen acceptor, see: Sanz, R.; Escribano, J.; Pedrosa, M. R.; Aguado, R.; Arnaiz, F. J. Adv. Synth. Catal. 2007, 349, 713.
    • 3 as oxygen acceptor, see: Sanz, R.; Escribano, J.; Pedrosa, M. R.; Aguado, R.; Arnaiz, F. J. Adv. Synth. Catal. 2007, 349, 713.
  • 17
    • 33746864043 scopus 로고    scopus 로고
    • For a recent review, see
    • For a recent review, see: Humphrey, G. R.; Kuethe, J. T. Chem. Rev. 2006, 106, 2875.
    • (2006) Chem. Rev , vol.106 , pp. 2875
    • Humphrey, G.R.1    Kuethe, J.T.2
  • 26
    • 41349115186 scopus 로고
    • Adapted from: Eur. Pat. Appl. EP 3670 19790822, 94079
    • Adapted from: Holan, G.; Walser, R. A. Eur. Pat. Appl. EP 3670 19790822, 1979; Chem. Abstr. 1979, 92, 94079.
    • (1979) Chem. Abstr , vol.92
    • Holan, G.1    Walser, R.A.2
  • 27
    • 41349088527 scopus 로고    scopus 로고
    • Using methyl 2-(2-nitro-4-trifluoromethoxyphenyl)-3-phenylpropenoate. No yield was given. See: Davies, I. W, Smitrovich, J. H, Qu, C. PCT Int. Appl. WO 2005000804, 2005; Chem. Abstr. 2005, 142, 113888
    • Using methyl 2-(2-nitro-4-trifluoromethoxyphenyl)-3-phenylpropenoate. No yield was given. See: Davies, I. W.; Smitrovich, J. H.; Qu, C. PCT Int. Appl. WO 2005000804, 2005; Chem. Abstr. 2005, 142, 113888.
  • 29
    • 0036229887 scopus 로고    scopus 로고
    • For related trans-etherifications using the same substrate, see: (a) Jonczyk, A.; Kowalkowska, A. Synthesis 2002, 674.
    • For related trans-etherifications using the same substrate, see: (a) Jonczyk, A.; Kowalkowska, A. Synthesis 2002, 674.
  • 37
    • 27744542989 scopus 로고    scopus 로고
    • To our knowledge, only two condensation reactions of 2-(2-nitrophenyl) ethanoates with aliphatic aldehydes have been reported: (a) Palmer, F. N.; Lach, F.; Poriel, C.; Pepper, A. G.; Bagley, M. C.; Slawin, A. M. Z.; Moody, C. J. Org. Biomol. Chem. 2005, 3, 3805.
    • To our knowledge, only two condensation reactions of 2-(2-nitrophenyl) ethanoates with aliphatic aldehydes have been reported: (a) Palmer, F. N.; Lach, F.; Poriel, C.; Pepper, A. G.; Bagley, M. C.; Slawin, A. M. Z.; Moody, C. J. Org. Biomol. Chem. 2005, 3, 3805.
  • 39
    • 41349092210 scopus 로고    scopus 로고
    • Formation of quinolines have been observed in transition-metal-catalyzed reductive annulations of β-(2-nitrophenyl)-α,β-unsaturated ketones and aldehydes. These reactions probably occur by initial reduction of the nitro-group to an amine, followed by condensation with the carbonyl. See: (a) Watanabe, Y, Takatsuki, K, Shim, S. C. Bull. Chem. Soc. Jpn. 1978, 51, 3397
    • Formation of quinolines have been observed in transition-metal-catalyzed reductive annulations of β-(2-nitrophenyl)-α,β-unsaturated ketones and aldehydes. These reactions probably occur by initial reduction of the nitro-group to an amine, followed by condensation with the carbonyl. See: (a) Watanabe, Y.; Takatsuki, K.; Shim, S. C. Bull. Chem. Soc. Jpn. 1978, 51, 3397.
  • 40
    • 41349116050 scopus 로고    scopus 로고
    • See also reference 1f
    • (b) See also reference 1f.
  • 41
    • 41349098470 scopus 로고    scopus 로고
    • This compound was recently prepared in 55% yield using a similar procedure, see: Chen, G, Yee, D. J, Gubernator, N, Sames, D. PCT Int. Appl, WO2006026368, 2006; Chem. Abstr. 2006, 144, 292572
    • This compound was recently prepared in 55% yield using a similar procedure, see: Chen, G.; Yee, D. J.; Gubernator, N.; Sames, D. PCT Int. Appl., WO2006026368, 2006; Chem. Abstr. 2006, 144, 292572.
  • 42
    • 33845469909 scopus 로고    scopus 로고
    • For a preparation in 77% yield using tert-butyl 2-phenylthioethanoate, see: Makosza, M.; Winiarski, J. J. Org. Chem. 1984, 49, 1494.
    • For a preparation in 77% yield using tert-butyl 2-phenylthioethanoate, see: Makosza, M.; Winiarski, J. J. Org. Chem. 1984, 49, 1494.
  • 44
    • 41349114526 scopus 로고    scopus 로고
    • One carbon resonance was not observed
    • One carbon resonance was not observed.
  • 52
    • 41349096794 scopus 로고    scopus 로고
    • The reported mp for the dimethyl diester is 143-144°C.
    • The reported mp for the dimethyl diester is 143-144°C.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.