Synthesis and reactions of haloazodienes. A new and general synthesis of substituted pyridazines

MS South, TL Jakuboski, MD Westmeyer…

文献索引：South, Michael S.; Jakuboski, Terri L.; Westmeyer, Mark D.; Daniel Journal of Organic Chemistry, 1996 , vol. 61, # 25 p. 8921 - 8934

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被引用次数: 82

摘要

The reaction of dihalohydrazones with Hünig's base gives 1-carbethoxy-3-phenyl-4- haloazodienes in-situ, which were found to combine with a variety of electron rich olefins to yield halo-substituted tetrahydropyridazines (Scheme 2 and Table 1). These haloazodiene cyclizations are best characterized as inverse electron demand, 4+ 2 hetero Diels-Alder reactions that maintain a high degree of regio-and stereochemical control (Schemes 5 ...