B(C6F5)3-Catalyzed Highly Chemoselective Reduction of Isatins: Synthesis of Indolin-3-ones and Indolines
A chemo- and site-selective reduction reaction of isatin derivatives using catalyst B(C6F5)3 and hydrosilanes is described. This transformation is operationally simple, proceeds under mild conditions, and is resistant to various functional groups. Thus, this efficient reaction using a combination of B(C6F5)3 and BnMe2SiH or B(C6F5)3 and Et2SiH2 could potentially be utilized to produce various indolin-3-ones and indolines, without the need for multistep procedures and metal catalysis conditions.
Jeong, Hyojin,Han, Nara,Hwang, Dong Wook,Ko, Haye Min
supporting information
p. 8150 - 8155
(2020/11/02)
PPh3 Mediated Reductive Annulation Reaction between Isatins and Electron Deficient Dienes to Construct Spirooxindole Compounds
A PPh3 mediated reductive annulation reaction between isatins and 4,4-dicyano-2-methylenebut-3-enoates was developed. The reaction provided an alternative method for constructing five- and three-membered all-carbon spirooxindole compounds. Lith
Features of interaction of 1-hydroxymethylisatin with certain P-, S-, and C-electrophiles
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Bogdanov,Il'In,Musin,Mironov
p. 1198 - 1200
(2015/06/25)
SEMICARBAZONES AND THIOSEMICARBAZONES OF THE HETEROCYCLIC SERIES. XLVIII. REACTION OF 1-ACETYLISATINS WITH THIOSEMICARBAZIDES
In reaction with thiosemicarbazides 1-acylisatins form the thiosemicarbazides of N-acylisatinic acids in addition to the thiosemicarbazones.The yields of the thiosemicarbazides increase with increase in the electron-withdrawing effect of the acyl residue or with substitution of a hydrogen atom in the primary thioamide group of the initial thiosemicarbazides by alkyl radicals.The reaction products are capable of transformation to the 3-thiosemicarbazones of 1-acylisatins.The latter were isolated in the form of E and Z isomers, and their mutual transitions were investigated.The five-membered ring of 1-acetylisatin thiosemi carbazone opens in an alkaline medium with the formation of the thiosemicarbazone of N-acetylisatinic acid.Contrary to previous data, this compound does not undergo direct cyclization to the 1,2,4-triazinoindole derivatives.
Tomchin, A. B.,Krylova, I. M.
p. 2173 - 2186
(2007/10/02)
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