含哒嗪环的特殊双环内过氧化物的合成与化学性质
Synthesis and chemistry of unusual bicyclic endoperoxides containing the pyridazine ring.
作者信息
Ozer Galip, Saraçoğlu Nurullah, Balci Metin
机构信息
Department of Chemistry, Faculty of Art and Sciences, Atatürk University, 25240 Erzurum, Turkey.
出版信息
J Org Chem. 2003 Sep 5;68(18):7009-15. doi: 10.1021/jo0345300.
Inverse-Diels-Alder reaction of dimethyl 1,2,4,5-tetrazine-3,6-dicarboxylate with unsaturated bicyclic endoperoxides gave the bicyclic endoperoxides containing the pyridazine ring. The NEt(3) and CoTPP (TPP = tetraphenylporphyrin) catalyzed reaction of endoperoxide 8 resulted in the formation of hydroxy ketone 11 and cis-diol 9. Cleavage of the peroxide linkage in 8 with thiourea provided cis-diol 9. Oxidation of hydroxy ketone 11 and cis-diol 9 led to the phthalazine-5,8-dione 10. Furthermore, the various transformations of the other endoperoxides 19, 20, 22, 23, and 30 resulted in the formation of pyridazine derivatives.
1,2,4,5-四嗪-3,6-二甲酸二甲酯与不饱和双环内过氧化物的逆狄尔斯-阿尔德反应生成了含有哒嗪环的双环内过氧化物。内过氧化物8在三乙胺和四苯基卟啉钴（TPP = 四苯基卟啉）催化下反应生成羟基酮11和顺式二醇9。用硫脲裂解8中的过氧键得到顺式二醇9。羟基酮11和顺式二醇9的氧化生成酞嗪-5,8-二酮10。此外，其他内过氧化物19、20、22、23和30的各种转化反应生成了哒嗪衍生物。
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