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Volumn 107, Issue 20, 1985, Pages 5745-5754

Inverse Electron Demand Diels-Alder Reactions of Heterocyclic Azadienes: Formal Total Synthesis of Streptonigrin

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RUFOCROMOMYCIN;

EID: 0022398192     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00306a024     Document Type: Article
Times cited : (158)

References (27)
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    • Structures 6a-c, e, f, h, and i were verified by exhaustive decarboxylation (LiCl, wet Me2SO, 170 °C) as follows: 6a afforded 4-methyl-3-phenylpyridine 6b and 6h afforded 4-phenylpyridine (Aldrich Chemical Co.). 6c and 6i afforded 3-methyl-4-phenylpyridine (Abramovitch, R. A.; Saha, M. Can. J. Chem. 1966, 44, 1765). 6e afforded 3-phenylpyridine (Aldrich Chemical Co.). 6a and 6c are isomeric of one another. 6b is isomeric with 6e. 6f afforded 3-ethyl-4-methylpyridine (ICN K and K Laboratories).
    • 2SO, 170 °C) as follows: 6a afforded 4-methyl-3-phenylpyridine (Pridgen, L. N. J. Heterocycl. Chem. 1975, 12, 443). 6b and 6h afforded 4-phenylpyridine (Aldrich Chemical Co.). 6c and 6i afforded 3-methyl-4-phenylpyridine (Abramovitch, R. A.; Saha, M. Can. J. Chem. 1966, 44, 1765). 6e afforded 3-phenylpyridine (Aldrich Chemical Co.). 6a and 6c are isomeric of one another. 6b is isomeric with 6e. 6f afforded 3-ethyl-4-methylpyridine (ICN K and K Laboratories).
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    • 2] or with the use of tris-(p-bromophenyl)hexachloroantimonate [see: Bell, F. A.; Ledwith, A.; Sherrington, D. C. J. Chem Soc. C 1969, 2719] were unsuccessful and promoted decomposition of enamine 20a. (d) Dauben, W. G.; Kozikowski, A. P. J. Am. Chem. Soc. 1974, 96, 3664. Dauben, W. G.; Krabbenhoft, H. O. J. Org. Chem. 1977, 42, 282.
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    • 2 under reduced pressure. All reactions requiring anhydrous conditions were run under a nitrogen atmosphere in oven-dried glassware. All other solvents and reagents were used as received from commercial sources. Pressure reactions, 6.2 kbar, were conducted in a pressure generator available from Leco Corp. 30cin glass-plug-sealed, heat-shrinkable Teflon tubing, (b) (c) DeShong, P.; Dicken, C. M.; Perez, J. J.; Shoff, R. M.Org. Prep. Proced. Int. 1982, 14, 369. The pressure-promoted reactions were carried out in a AGP-10002 pressure generator manufactured by Leco Corp. Tem-Pres Division, Belle-fonte, PA 16823
    • 2 under reduced pressure. All reactions requiring anhydrous conditions were run under a nitrogen atmosphere in oven-dried glassware. All other solvents and reagents were used as received from commercial sources. Pressure reactions, 6.2 kbar, were conducted in a pressure generator available from Leco Corp.30cin glass-plug-sealed, heat-shrinkable Teflon tubing, (b) Meyers, A. I.; Slade, J.; Smith, R. K.; Mihelich, E. D.; Hershenson, F. M.; Liang, C. D. J. Org. Chem. 1979, 44, 2247. (c) DeShong, P.; Dicken, C. M.; Perez, J. J.; Shoff, R. M. Org. Prep. Proced. Int. 1982, 14, 369. The pressure-promoted reactions were carried out in a AGP-10002 pressure generator manufactured by Leco Corp. Tem-Pres Division, Belle-fonte, PA 16823.
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