Nakamura Yoshinori, Ukita Tatsuzo
Discovery Research Laboratory, Tanabe Seiyaku Co., Ltd., 3-16-89, Kashima, Yodogawa, Osaka 532-8505, Japan.
Org Lett. 2002 Jul 11;4(14):2317-20. doi: 10.1021/ol025916k.
[reaction: see text] alpha-Diazophosphonates, which have extremely useful properties from a synthetic point of view, are disclosed as 1,1-ambiphilic one-carbon building blocks for one-pot construction of various heterocyclic compounds. They are easily prepared and have higher stability by the effect of the phosphoryl group than corresponding alpha-diazocarbonyl compounds. Using this synthon, we have developed a novel, mild, and efficient synthetic method of 2,3-disubstituted indoles and 3,4-disubstituted isocoumarins.
[反应:见正文]α-重氮膦酸酯从合成角度来看具有极其有用的性质,被公开作为用于一锅法构建各种杂环化合物的1,1-双亲性一碳结构单元。它们易于制备,并且由于磷酰基的作用比相应的α-重氮羰基化合物具有更高的稳定性。使用这种合成子,我们开发了一种新颖、温和且高效的合成2,3-二取代吲哚和3,4-二取代异香豆素的方法。