메뉴 건너뛰기




Volumn 73, Issue 21, 2008, Pages 8437-8447

Povarov reactions involving 3-aminocoumarins: Synthesis of 1,2,3,4-tetrahydropyrido[2,3-c]coumarins and pyrido[2,3-c]coumarins

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDES; HYDROCARBONS; OLEFINS; YTTERBIUM;

EID: 55249117944     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo801411p     Document Type: Article
Times cited : (84)

References (130)
  • 1
    • 33847274696 scopus 로고    scopus 로고
    • For review articles on multicomponent reactions see: a
    • For review articles on multicomponent reactions see: (a) Tejedor, D.; Garcia-Tellado, F. Chem. Soc. Rev. 2007, 36, 484-491.
    • (2007) Chem. Soc. Rev , vol.36 , pp. 484-491
    • Tejedor, D.1    Garcia-Tellado, F.2
  • 6
    • 0001134412 scopus 로고    scopus 로고
    • Angew. Chem., Int. Ed. 2000, 39, 3168-3210.
    • (2000) Angew. Chem., Int. Ed , vol.39 , pp. 3168-3210
  • 10
  • 16
    • 0034788066 scopus 로고    scopus 로고
    • For example: (a) (±)-Preemulia coumarin. Appendino, G.; Cravotto, G.; Minassi, A.; Palmisano, G. Eur. J. Org. Chem. 2001, 3711-3717.
    • For example: (a) (±)-Preemulia coumarin. Appendino, G.; Cravotto, G.; Minassi, A.; Palmisano, G. Eur. J. Org. Chem. 2001, 3711-3717.
  • 18
    • 0004506586 scopus 로고    scopus 로고
    • (±)-Magnoshinin. Yoshida, S.; Ogiku, T.; Ohmizu, H.; Iwasaki, T. Synlett 1994, 895-898.
    • (c) (±)-Magnoshinin. Yoshida, S.; Ogiku, T.; Ohmizu, H.; Iwasaki, T. Synlett 1994, 895-898.
  • 19
    • 0000796911 scopus 로고    scopus 로고
    • (-)-Decarbamoylsaxitoxin. Yong, C.; Kishi, Y. J. Am. Chem. Soc. 1992, 114, 7001-7006.
    • (d) (-)-Decarbamoylsaxitoxin. Yong, C.; Kishi, Y. J. Am. Chem. Soc. 1992, 114, 7001-7006.
  • 20
    • 0019186783 scopus 로고    scopus 로고
    • (+)-Furanomycin. Semple, J. E.; Wang, P. C.; Lysenko, Z.; Joullié, M. M. J. Am. Chem. Soc. 1980, 102, 7505-7510.
    • (e) (+)-Furanomycin. Semple, J. E.; Wang, P. C.; Lysenko, Z.; Joullié, M. M. J. Am. Chem. Soc. 1980, 102, 7505-7510.
  • 53
  • 63
    • 42049092950 scopus 로고    scopus 로고
    • Sridharan, V, Avendano, C, Menéndez, J. C. Synthesis 2008, 1039-1044. Also see ref 5
    • (x) Sridharan, V.; Avendano, C.; Menéndez, J. C. Synthesis 2008, 1039-1044. Also see ref 5.
  • 69
    • 0141518222 scopus 로고    scopus 로고
    • Also see refs 7k and 10b
    • (a) Powell, D. A.; Batey, R. A. Tetrahedron Lett. 2003, 44, 7569-7573. Also see refs 7k and 10b.
    • (2003) Tetrahedron Lett , vol.44 , pp. 7569-7573
    • Powell, D.A.1    Batey, R.A.2
  • 85
    • 34250357101 scopus 로고
    • (d) Linch, F. W. J. Chem. Soc. 1912, 101, 1759-1765.
    • (1912) J. Chem. Soc , vol.101 , pp. 1759-1765
    • Linch, F.W.1
  • 86
    • 34250331479 scopus 로고
    • (e) Linch, F. W. J. Chem. Soc. 1912, 101, 1755-1759.
    • (1912) J. Chem. Soc , vol.101 , pp. 1755-1759
    • Linch, F.W.1
  • 92
    • 55249116857 scopus 로고    scopus 로고
    • 4 Å molecular sieves were added to the reaction mixture, and the rest of the procedure was same as reported by Bishnoi; see ref 14e
    • 4 Å molecular sieves were added to the reaction mixture, and the rest of the procedure was same as reported by Bishnoi; see ref 14e.
  • 94
    • 55249119612 scopus 로고    scopus 로고
    • 1H NMR analysis of crude reaction mixture.
    • 1H NMR analysis of crude reaction mixture.
  • 95
    • 33144469893 scopus 로고    scopus 로고
    • For some discussions on concerted and stepwise mechanisms of Diels-Alder reactions, see: a
    • For some discussions on concerted and stepwise mechanisms of Diels-Alder reactions, see: (a) Bongini, A.; Panunzio, M. Eur. J. Org. Chem. 2006, 972-977.
    • (2006) Eur. J. Org. Chem , pp. 972-977
    • Bongini, A.1    Panunzio, M.2
  • 98
    • 55249108326 scopus 로고    scopus 로고
    • At room temperature, the reaction with 4-bromostyrene showed no signs of progress after 4 h. So, it was then heated at reflux
    • At room temperature, the reaction with 4-bromostyrene showed no signs of progress after 4 h. So, it was then heated at reflux.
  • 100
    • 0000510639 scopus 로고    scopus 로고
    • For representative examples, see; a
    • For representative examples, see; (a) Yamanaka, M.; Nishida, A.; Nakagawa, M. Org. Lett. 2000, 2, 159-161.
    • (2000) Org. Lett , vol.2 , pp. 159-161
    • Yamanaka, M.1    Nishida, A.2    Nakagawa, M.3
  • 102
    • 17744387757 scopus 로고    scopus 로고
    • For examples of silica gel as a Lewis acid, see: (a) Hudlicky, T, Rinner, U, Finn, K. J, Ghiviriga, I. J. Org. Chem. 2005, 70, 3490-3499
    • For examples of silica gel as a Lewis acid, see: (a) Hudlicky, T.; Rinner, U.; Finn, K. J.; Ghiviriga, I. J. Org. Chem. 2005, 70, 3490-3499.
  • 105
    • 55249120300 scopus 로고    scopus 로고
    • Ph.D. Dissertation, Memorial University of Newfoundland
    • Pottie, I. R. Ph.D. Dissertation, Memorial University of Newfoundland, 2002.
    • (2002)
    • Pottie, I.R.1
  • 106
    • 55249084764 scopus 로고    scopus 로고
    • Prepared from 4-acetylpyrrole-2-carboxaldehyde by reaction with NaH and methyl chloroformate. For the preparation of 4-acetylpyrrole-2-carboxaldehyde, see: Anderson, H. J.; Loader, C. E.; Foster, A. Can. J. Chem. 1978, 58, 2527-2530.
    • Prepared from 4-acetylpyrrole-2-carboxaldehyde by reaction with NaH and methyl chloroformate. For the preparation of 4-acetylpyrrole-2-carboxaldehyde, see: Anderson, H. J.; Loader, C. E.; Foster, A. Can. J. Chem. 1978, 58, 2527-2530.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.