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Volumn 74, Issue C, 2007, Pages 101-124

Methodology for the synthesis of pyridines and pyridones: Development and applications

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EID: 40749083200     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article
Times cited : (37)

References (107)
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    • Kametani's pioneering studies on streptonigrin are especially informative:. Kametani T., Kozuka A., and Tanaka S. Yakugaku Zasshi 90 (1970) 1574
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    • The term "cycloaddition" as used in this paper is only meant to describe the outcome of the reaction of a conjugated carbonyl compound with a vinyl ether, and it should not be construed as implying any particular mechanism for the process.
    • The term "cycloaddition" as used in this paper is only meant to describe the outcome of the reaction of a conjugated carbonyl compound with a vinyl ether, and it should not be construed as implying any particular mechanism for the process.
  • 12
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    • The major frontier orbital interaction involved in this process occurs between the HOMO of the vinyl ether and the LUMO of the enone. Conjugation of the enecarbonyl system with an aryl group lowers the LUMO energy (EHMO calculations), diminishing the HOMO-LUMO gap and accelerating the reaction.
    • The major frontier orbital interaction involved in this process occurs between the HOMO of the vinyl ether and the LUMO of the enone. Conjugation of the enecarbonyl system with an aryl group lowers the LUMO energy (EHMO calculations), diminishing the HOMO-LUMO gap and accelerating the reaction.
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    • Interestingy, lanthanide complexes are poor catalysts for the analogous reaction of simple aliphatic enones. For an exceptional case see:
    • Interestingy, lanthanide complexes are poor catalysts for the analogous reaction of simple aliphatic enones. For an exceptional case see:. Chapleur Y., and Euvrard M.-N. J. Chem. Soc., Chem. Commun. (1987) 884
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    • Ethanol was initially employed as the solvent in this step (see ref. 10), but MeCN was later found to be superior. In many cases, the use of MeCN is essential to achieve an efficient conversion.
    • Ethanol was initially employed as the solvent in this step (see ref. 10), but MeCN was later found to be superior. In many cases, the use of MeCN is essential to achieve an efficient conversion.
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    • That such failures are due primarily to steric or to electronic problems is borne out of computational investigations (EHMO and MM+ methods).
    • That such failures are due primarily to steric or to electronic problems is borne out of computational investigations (EHMO and MM+ methods).
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    • This compound was not a known natural product at that time, but it was subsequently isolated from Cynanchum vincetoxicum:. Strk D., Lykkeberg A.K., Christensen J., Budnik B.A., Abe F., and Jaroszewski J.W. J. Nat. Prod. 65 (2002) 1299
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    • We presume that the reaction actually proceeds through a 4-electron electrocyclization of the singlet nitrene, followed by a [1,5]-sigmatropic H shift.
    • We presume that the reaction actually proceeds through a 4-electron electrocyclization of the singlet nitrene, followed by a [1,5]-sigmatropic H shift.
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    • Controversy persists regarding the precise mechanism of such reactions, especially with regard to the spin state of the nitrene:
    • Controversy persists regarding the precise mechanism of such reactions, especially with regard to the spin state of the nitrene:. Smolinsky G. J. Am. Chem. Soc. 83 (1961) 2489
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    • Thermolysis of 69 also proceeded smoothly; however, the ensuing carboline resisted oxidation of the pyridine C-6 methyl group, arguably due to the presence of the electron-donating N-substituent on the pyridine ring:
    • Thermolysis of 69 also proceeded smoothly; however, the ensuing carboline resisted oxidation of the pyridine C-6 methyl group, arguably due to the presence of the electron-donating N-substituent on the pyridine ring:. Wittek P.J., Liao T.K., and Cheng C.C. J. Org. Chem. 44 (1979) 870
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    • The sensitivity of diacylethylenes to the basic conditions of Table 5 mandated such experimental modifications.
    • The sensitivity of diacylethylenes to the basic conditions of Table 5 mandated such experimental modifications.
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    • For synthetic activity prior to 2002 see refs. 44 and 56. Recent efforts:
    • For synthetic activity prior to 2002 see refs. 44 and 56. Recent efforts:. Bowman W.R., Cloonan M.O., Fletcher A.J., and Stein T. Org. Biomol. Chem. 3 (2005) 1460
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    • For similar Pd-mediated reactions of 2-chloroquinolines see:
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