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Volumn 73, Issue 5, 2008, Pages 1987-1990

Three-component coupling reaction and cyclization of N-tosylimines and TMS-substituted propiolate mediated by DABCO

Author keywords

[No Author keywords available]

Indexed keywords

BIFUNCTIONAL SUBSTRATE; COUPLING REACTION;

EID: 41149148298     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo702649q     Document Type: Article
Times cited : (15)

References (42)
  • 22
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    • For the reaction of N-tosylimines catalyzed by tertiary amines, see: (a) Li, C.-Q.; Shi, M. Org. Lett. 2003, 5, 4273.
    • For the reaction of N-tosylimines catalyzed by tertiary amines, see: (a) Li, C.-Q.; Shi, M. Org. Lett. 2003, 5, 4273.
  • 24
    • 0141885412 scopus 로고    scopus 로고
    • For three-component coupling reaction based on Morita-Baylis-Hillman reaction, see: a
    • For three-component coupling reaction based on Morita-Baylis-Hillman reaction, see: (a) Evans, C. A.; Miller, S. J. J. Am. Chem. Soc. 2003, 125, 12394.
    • (2003) J. Am. Chem. Soc , vol.125 , pp. 12394
    • Evans, C.A.1    Miller, S.J.2
  • 25
    • 0037471214 scopus 로고    scopus 로고
    • For nickel-catalyzed three-component coupling of alkynes and imines, see: b
    • For nickel-catalyzed three-component coupling of alkynes and imines, see: (b) Patel, S.; Jamison, T. F. Angew. Chem., Int. Ed. 2003, 42, 1364.
    • (2003) Angew. Chem., Int. Ed , vol.42 , pp. 1364
    • Patel, S.1    Jamison, T.F.2
  • 26
    • 41149112680 scopus 로고    scopus 로고
    • We have thoroughly explored optimal reaction conditions using various solvents, tertiary amines, time and temperature, and equivalents of the reagents. However, an improved result over a 47% yield could not be obtained. Details of these examinations are described in Supporting Information
    • We have thoroughly explored optimal reaction conditions using various solvents, tertiary amines, time and temperature, and equivalents of the reagents. However, an improved result over a 47% yield could not be obtained. Details of these examinations are described in Supporting Information.
  • 27
    • 41149162413 scopus 로고    scopus 로고
    • Besides the desired olefin products 2, unreacted imines were detected in the reaction mixture, which were hydrolyzed during a workup process.
    • Besides the desired olefin products 2, unreacted imines were detected in the reaction mixture, which were hydrolyzed during a workup process.
  • 28
    • 33846250463 scopus 로고    scopus 로고
    • For recent examples of organocatalyzed syntheses of the chromene-type skeleton from salicyl aldehydes, see: (a) Sunden, H, Ibrahem, I, Zhao, G.-L, Eriksson, L, Cordova, A. Chem, Eur. J. 2007, 13, 574
    • For recent examples of organocatalyzed syntheses of the chromene-type skeleton from salicyl aldehydes, see: (a) Sunden, H.; Ibrahem, I.; Zhao, G.-L.; Eriksson, L.; Cordova, A. Chem. - Eur. J. 2007, 13, 574.
  • 34
    • 41149142129 scopus 로고    scopus 로고
    • Considering harmfulness of benzene, the reaction of 5a was investigated using toluene as an alternative solvent, providing a comparable result (110°C, 3 h, 72% yield) with the case of benzene.
    • Considering harmfulness of benzene, the reaction of 5a was investigated using toluene as an alternative solvent, providing a comparable result (110°C, 3 h, 72% yield) with the case of benzene.
  • 35
    • 41149153111 scopus 로고    scopus 로고
    • We suppose that the mechanism of the cyclization reaction (formation of 8) follows the same pathway as depicted in Scheme 2 in an intramolecular fashion because the same reaction in the presence of CD3-OD (this deuterium ought to be exchanged for the phenolic hydrogen of 5) gave the product 6 in which the deuterium was incorporated at the 2-position (as well as the methoxy hydrogens).
    • We suppose that the mechanism of the cyclization reaction (formation of 8) follows the same pathway as depicted in Scheme 2 in an intramolecular fashion because the same reaction in the presence of CD3-OD (this deuterium ought to be exchanged for the phenolic hydrogen of 5) gave the product 6 in which the deuterium was incorporated at the 2-position (as well as the methoxy hydrogens).
  • 36
    • 22244463229 scopus 로고    scopus 로고
    • For recent reports on chromene-forming reaction of salicyl N- tosylimine and conjugated alkynes or allenic esters, relating to our reaction systems but via a different reaction pathway, see: (a) Shi, Y.-L.; Shi, M. Org. Lett. 2005, 7, 3057.
    • For recent reports on chromene-forming reaction of salicyl N- tosylimine and conjugated alkynes or allenic esters, relating to our reaction systems but via a different reaction pathway, see: (a) Shi, Y.-L.; Shi, M. Org. Lett. 2005, 7, 3057.
  • 40
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    • For reports on allylation of benzopyrylium derivatives, see: a
    • For reports on allylation of benzopyrylium derivatives, see: (a) Lee, Y. G.; Ishimaru, K.; Iwasaki, H.; Ohkata, K.; Akiba, K. J. Org. Chem. 1991, 56, 2058.
    • (1991) J. Org. Chem , vol.56 , pp. 2058
    • Lee, Y.G.1    Ishimaru, K.2    Iwasaki, H.3    Ohkata, K.4    Akiba, K.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.