메뉴 건너뛰기




Volumn 46, Issue 21, 2007, Pages 3931-3933

Synthesis of 2,3-disubstituted indoles by a rhodium-catalyzed aromatic amino-claisen rearrangement of N-propargyl anilines

Author keywords

Alkynes; Cyclization; Heterocycles; Rearrangement; Rhodium

Indexed keywords

CATALYSTS; CRYSTALLINE MATERIALS; CYCLIZATION; DERIVATIVES; PROPANE; SYNTHESIS (CHEMICAL);

EID: 34250693162     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200605162     Document Type: Article
Times cited : (69)

References (48)
  • 4
    • 0034637490 scopus 로고    scopus 로고
    • For a recent intramolecular hydroarylation-type reaction, see: a
    • For a recent intramolecular hydroarylation-type reaction, see: a) N. Chatani, H. Inoue, T. Ikeda, S. Murai, J. Org. Chem. 2000, 65, 4913-4918;
    • (2000) J. Org. Chem , vol.65 , pp. 4913-4918
    • Chatani, N.1    Inoue, H.2    Ikeda, T.3    Murai, S.4
  • 6
    • 0035905577 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2001, 40, 4754-4757;
    • (2001) Chem. Int. Ed , vol.40 , pp. 4754-4757
    • Angew1
  • 14
    • 34250769961 scopus 로고    scopus 로고
    • See also, d K. B. Erzhanov, S. S. Kolkhosova, T. Sadykov, Zh. Org. Khim. 1989, 25, 1729-1732 (Chemical Abstracts: 112, 178623);
    • See also, d) K. B. Erzhanov, S. S. Kolkhosova, T. Sadykov, Zh. Org. Khim. 1989, 25, 1729-1732 (Chemical Abstracts: 112, 178623);
  • 16
    • 33845471185 scopus 로고
    • For a review, see: a
    • For a review, see: a) R. P. Lutz, Chem. Rev. 1984, 84, 205-247;
    • (1984) Chem. Rev , vol.84 , pp. 205-247
    • Lutz, R.P.1
  • 19
    • 4544320494 scopus 로고    scopus 로고
    • For a related monograph, see:, Wiley-VCH, Weinheim
    • For a related monograph, see: N. Krause, A. S. K. Hashmi, Modern Allene Chemistry, Vol. 1, Wiley-VCH, Weinheim, 2004, pp. 1-50.
    • (2004) Modern Allene Chemistry , vol.1 , pp. 1-50
    • Krause, N.1    Hashmi, A.S.K.2
  • 22
    • 84987532000 scopus 로고    scopus 로고
    • for a Brønsted acid promoted rearrangement, see: P. Barmettler, H.-J. Hansen, Helv. Chim. Acta 1990, 73, 1515-1573.
    • c) for a Brønsted acid promoted rearrangement, see: P. Barmettler, H.-J. Hansen, Helv. Chim. Acta 1990, 73, 1515-1573.
  • 23
    • 34250708438 scopus 로고    scopus 로고
    • There is yet another possible mechanism in Cu-promoted cyclizations of N-propargyl anilines (such as hydroarylation-type reactions). See: a) R. D. Dillard, D. E. Pavey, D. N. Benslay, J. Med. Chem. 1973, 16, 253;
    • There is yet another possible mechanism in Cu-promoted cyclizations of N-propargyl anilines (such as hydroarylation-type reactions). See: a) R. D. Dillard, D. E. Pavey, D. N. Benslay, J. Med. Chem. 1973, 16, 253;
  • 26
    • 84985111128 scopus 로고    scopus 로고
    • The aromatic Claisen rearrangements of propargyl ether derivatives usually afford fused arenes containing a six-membered ring: a U. Koch-Pomeranz, H.-J. Hansen, H. Schmid, Helv. Chim. Acta 1973, 56, 2981-3004;
    • The aromatic Claisen rearrangements of propargyl ether derivatives usually afford fused arenes containing a six-membered ring: a) U. Koch-Pomeranz, H.-J. Hansen, H. Schmid, Helv. Chim. Acta 1973, 56, 2981-3004;
  • 29
    • 33744870975 scopus 로고    scopus 로고
    • For a recent synthesis of indole compounds that involves a transition-metal-catalyzed cyclization, see: a
    • For a recent synthesis of indole compounds that involves a transition-metal-catalyzed cyclization, see: a) R. C. Larock, E. K. Yum, M. D. Refvik, J. Org. Chem. 1998, 63, 7652-7662;
    • (1998) J. Org. Chem , vol.63 , pp. 7652-7662
    • Larock, R.C.1    Yum, E.K.2    Refvik, M.D.3
  • 36
    • 4544278307 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2004, 43, 4063-4067.
    • (2004) Chem. Int. Ed , vol.43 , pp. 4063-4067
    • Angew1
  • 43
    • 34250742450 scopus 로고    scopus 로고
    • Although the formation mechanism of 4c and 18 remains unclear at present, it may involve the hydrogenation of a 1,2-dihydroquinoline derivative formed from 1c or 16 according to Scheme 1. However, the corresponding quinoline compounds, which are considered to be oxidized products, were not detected. See also: T. P. Forrest, G. A. Dauphinee, S. A. Deraniyagala, Can. J. Chem. 1985, 63, 412-417 and references [4a] and [16
    • Although the formation mechanism of 4c and 18 remains unclear at present, it may involve the hydrogenation of a 1,2-dihydroquinoline derivative formed from 1c or 16 according to Scheme 1. However, the corresponding quinoline compounds, which are considered to be oxidized products, were not detected. See also: T. P. Forrest, G. A. Dauphinee, S. A. Deraniyagala, Can. J. Chem. 1985, 63, 412-417 and references [4a] and [16].
  • 44
    • 34250751767 scopus 로고    scopus 로고
    • A similar observation has been reported in the Brønsted acid-catalyzed rearrangement of N-propargyl anilines. See reference [5c].
    • A similar observation has been reported in the Brønsted acid-catalyzed rearrangement of N-propargyl anilines. See reference [5c].
  • 45
    • 34250699458 scopus 로고    scopus 로고
    • The authors acknowledge the referees for their suggestion to examine the reaction of 1f.
    • The authors acknowledge the referees for their suggestion to examine the reaction of 1f.
  • 46
    • 0037295193 scopus 로고    scopus 로고
    • Although it has been reported that the activation mechanism in a transition-metal-promoted amino-Claisen rearrangement probably involves activation of the alkyne unit, as in metal-catalyzed hydroarylation, the amine unit can also be activated by the metal. See references [4a, 7, and [8, and Y. Yamamoto, J. Seta, H. Murooka, X.-H. Han, Inorg. Chem. Commun. 2003, 6, 202-205
    • Although it has been reported that the activation mechanism in a transition-metal-promoted amino-Claisen rearrangement probably involves activation of the alkyne unit, as in metal-catalyzed hydroarylation, the amine unit can also be activated by the metal. See references [4a], [7], and [8], and Y. Yamamoto, J. Seta, H. Murooka, X.-H. Han, Inorg. Chem. Commun. 2003, 6, 202-205.
  • 47
    • 1642603931 scopus 로고    scopus 로고
    • 2-Propanol was used as a hydrogen source in the transition-metal- catalyzed hydrogenation of 1,2-dihydroquinolines: a K. Fujita, C. Kitatsuji, S. Furukawa, R. Yamaguchi, Tetrahedron Lett. 2004, 45, 3215-3217;
    • 2-Propanol was used as a hydrogen source in the transition-metal- catalyzed hydrogenation of 1,2-dihydroquinolines: a) K. Fujita, C. Kitatsuji, S. Furukawa, R. Yamaguchi, Tetrahedron Lett. 2004, 45, 3215-3217;
  • 48
    • 34250774433 scopus 로고    scopus 로고
    • see reference [3b] for the Brønsted acid promoted hydrogenation of oxygen analogues.
    • b) see reference [3b] for the Brønsted acid promoted hydrogenation of oxygen analogues.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.