. alpha.-Nitroarylation of ketones and esters: an exceptionally facile synthesis of indoles, 2-indolinones and arylacetic acids

TV RajanBabu, BL Chenard…

Index: RajanBabu, T. V.; Chenard, Bertrand L.; Petti, Michael A. Journal of Organic Chemistry, 1986 , vol. 51, # 10 p. 1704 - 1712

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Citation Number: 83

Abstract

Silyl enol ethers and ketene silyl acetals add to aromatic nitro compounds in the presence of fluoride ion sources to give dihydroaromatic nitronates which are readily oxidized to a- nitroaryl carbonyl compounds by DDQ or Br,. These versatile intermediates are readily converted into indoles or 2-indolinones by reductive cyclization. Since halogen substituents on the aromatic ring are not displaced in the initial alkylation reaction, nucleophilic ...

~78%

~54%

~61%

~72%

Structure-Activity Relationships of 2, N 6, 5'-Substituted A...

[Adachi, Hayamitsu; Palaniappan, Krishnan K.; Ivanov, Andrei A.; Bergman, Nathaniel; Gao, Zhan-Guo; Jacobson, Kenneth A. Journal of Medicinal Chemistry, 2007 , vol. 50, # 8 p. 1810 - 1827]