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Volumn , Issue 28, 2010, Pages 5373-5379

Streamlined access to functionalized chromenes and quinolines using domino reactions of salicylic aldehydes and methyl 4-chloro-2-butynoate

Author keywords

Cyclization; Domino reactions; Isomerization; Nitrogen heterocycles; Synthetic methods

Indexed keywords


EID: 77957132550     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.201000559     Document Type: Article
Times cited : (16)

References (31)
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    • Fravel, B.W.1
  • 2
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    • (Eds.: A. R. Katritzky, C. W. Rees, C. A. Ramsden, E. F. V. Scriven, R. J. K. Taylor), Pergamon, Oxford
    • C. H. McAteer, M. Balasubramanian, M. Murugan in Comprehensive Heterocyclic Chemistry III (Eds.: A. R. Katritzky, C. W. Rees, C. A. Ramsden, E. F. V. Scriven, R. J. K. Taylor), Pergamon, Oxford, 2008, vol. 7, pp. 309-336.
    • (2008) Comprehensive Heterocyclic Chemistry III , vol.7 , pp. 309-336
    • McAteer, C.H.1    Balasubramanian, M.2    Murugan, M.3
  • 6
    • 33745862400 scopus 로고    scopus 로고
    • and references cited therein
    • For a recent result, see: S. K. Ko, H. J. Jang, E. Kim, S. B. Park, Chem. Commun. 2006, 2962-2964, and references cited therein.
    • (2006) Chem. Commun. , pp. 2962-2964
    • Ko, S.K.1    Jang, H.J.2    Kim, E.3    Park, S.B.4
  • 10
    • 70350511196 scopus 로고    scopus 로고
    • and references cited therein
    • B. J. Cowen, S. J. Miller, Chem, Soc. Rev. 2009, 38, 3102-3116, and references cited therein.
    • (2009) Chem, Soc. Rev. , vol.38 , pp. 3102-3116
    • Cowen, B.J.1    Miller, S.J.2
  • 13
    • 77957115486 scopus 로고    scopus 로고
    • Preliminary calculations (geometry optimization, by molecular mechanics, semiempirical and DFT methods) indicate that compound 4a is more stable than the corresponding isomer 4a′ by around 23 kJ/mol
    • Preliminary calculations (geometry optimization, by molecular mechanics, semiempirical and DFT methods) indicate that compound 4a is more stable than the corresponding isomer 4a′ by around 23 kJ/mol.
  • 18
    • 77957126649 scopus 로고    scopus 로고
    • The use of unprotected anthranilic aldehyde led to complex mixtures
    • b) The use of unprotected anthranilic aldehyde led to complex mixtures.
  • 26
    • 74049152460 scopus 로고    scopus 로고
    • For alternative access to related quinoline derivatives through a .Friedländer annulation, see: D. S. Bose, M. Idrees, N. M. Jakka, J. V. Rao, J. Comb. Chem. 2010, 12, 100-110.
    • (2010) J. Comb. Chem. , vol.12 , pp. 100-110
    • Bose, D.S.1    Idrees, M.2    Jakka, N.M.3    Rao, J.V.4
  • 27
    • 52449091292 scopus 로고    scopus 로고
    • For a recent example of this transformation, see: C. Sun, B. Xu, J. Org. Chem, 2008, 73, 7361-7364.
    • (2008) J. Org. Chem , vol.73 , pp. 7361-7364
    • Sun, C.1    Xu, B.2
  • 29
    • 77957171695 scopus 로고    scopus 로고
    • Around 237,000 substances with this core are listed in SciFinder (2010), most being in biomedical patents
    • Around 237,000 substances with this core are listed in SciFinder (2010), most being in biomedical patents.
  • 30
    • 77957143380 scopus 로고    scopus 로고
    • Although in this study only two salicylic aldehydes and one anthranilic aldehyde have been, used, taking into account the reactivity precedents on related MBH-type reactions, we believe the methodology has a general application range, including substrates with different substituents and substitution patterns on the aromatic ring
    • Although in this study only two salicylic aldehydes and one anthranilic aldehyde have been, used, taking into account the reactivity precedents on related MBH-type reactions, we believe the methodology has a general application range, including substrates with different substituents and substitution patterns on the aromatic ring.
  • 31
    • 0037459871 scopus 로고    scopus 로고
    • 2 reagent was prepared accordingly to a literature procedure, see: A. K. Chakraborti, R. Gulhane, Tetrahedron Lett, 2003, 44, 3521-3525.
    • (2003) Tetrahedron Lett , vol.44 , pp. 3521-3525
    • Chakraborti, A.K.1    Gulhane, R.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.