Chemistry of diazocarbonyl compounds: XXX. Development of a synthetic approach to pyridazine structure via wittig reaction of fluoroalkyl-containing diazo keto esters |
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Authors: | S V Galiullina V M Zakharova G P Kantin V A Nikolaev |
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Institution: | (1) St. Petersburg State University, Universitetskii pr. 26, St. Petersburg, 198504, Russia |
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Abstract: | 3,4,6-Trisubstituted pyridazines were synthesized from fluoroalkyl-containing diazo keto esters in three steps along two different reaction sequences: (1) Wittig, Staudinger, and diaza-Wittig and (2) Staudinger, Wittig, and diaza-Wittig. According to the first of these with the initial Wittig reaction, the yield of the target 4-fluoroalkyl-substituted pyridazines is almost twice as large as in the reaction sequence involving the corresponding N-phosphanylidene derivatives as intermediates. In both sequences, the final steps (synthesis of vinylphosphazenes and the subsequent diaza-Wittig reaction) occurred as a tandem process, and intermediate vinylphosphazenes could not be isolated. Non-fluorinated diazo keto esters and the respective phosphazenes failed to react with alkoxycarbonylmethylidene(triphenyl)phosphoranes under the same conditions. |
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