Construction of heterocyclic compounds by use of alpha-diazophosphonates: new one-pot syntheses of indoles and isocoumarins.
[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.
Nakamura
Yoshinori
Y
Discovery Research Laboratory, Tanabe Seiyaku Co., Ltd., 3-16-89, Kashima, Yodogawa, Osaka 532-8505, Japan. y-naka@tanabe.co.jp
Ukita
Tatsuzo
T
D002384:Catalysis; D003374:Coumarins / Q000138:chemical synthesis* / Q000737:chemistry; D003979:Diazonium Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D007202:Indicators and Reagents; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D009943:Organophosphorus Compounds / Q000138:chemical synthesis* / Q000737:chemistry
D003374:Coumarins; D003979:Diazonium Compounds; D006571:Heterocyclic Compounds; D007202:Indicators and Reagents; D007211:Indoles; D009943:Organophosphorus Compounds