Triphenylphosphine-mediated reaction of dialkyl azodicarboxylate with activated alkenes leading to pyrazolines

Triphenylphosphine-mediated reaction of dialkyl azodicarboxylate with activated alkenes leading to pyrazolines
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三苯基膦介导的偶氮二甲酸二烷基酯与活化烯烃的反应生成吡唑啉

DOI:
10.1039/c2ra21249h
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发表时间:
2012
期刊:
影响因子:
3.9
通讯作者:
Y
Y
中科院分区:
化学3区
文献类型:
--
作者:
Yamazaki;S.; Maenaka;Y.; Fujinami;K.; Mikata;Y

文献摘要

相似文献

研究了由三苯膦和偶氮二羧酸酯衍生的Huisgen两性离子与活化烯烃的反应。各种乙烯三羧酸酯和偶氮二羧酸二乙酯与PPh_3反应,有效地得到吡唑啉。该吡唑啉合成也适用于2-取代的丙烯酸酯,例如2-膦酰基丙烯酸三甲酯和2-(三氟甲基)丙烯酸甲酯。通过与乙炔二羧酸和Huisgen两性离子反应的比较,讨论了可能的反应机理。对吡唑啉类化合物的选择性转化也进行了研究。
Reaction of the Huisgen zwitterions, derived from triphenylphosphine and azodicarboxylates with activated alkenes has been studied. The reaction of various ethenetricarboxylates and diethyl azodicarboxylate with PPh3 gave pyrazolines efficiently. This pyrazoline synthesis is also applicable to 2-substituted acrylates such as trimethyl 2-phosphonoacrylate and methyl 2-(trifluoromethyl)acrylate. The possible reaction mechanism was discussed in comparison with the reaction of acetylenedicarboxylate and Huisgen zwitterions. The selective transformation of pyrazoline products have also been performed.