Synthesis of 3-Hydroxy-4-arylquinolin-2-ones Including Viridicatol via a Darzens Condensation/Friedel-Crafts Alkylation Strategy
The new efficient synthesis of biologically important 3-hydroxy-4-arylquinolin-2-ones through the Darzens condensation (epoxidation) of dichloroacetanilides with aromatic aldehydes followed by one-pot dechlorative epoxide-arene cyclization is described. T
Mamedov, Vakhid A.,Mamedova, Vera L.,Kadyrova, Saniya F.,Galimullina, Venera R.,Khikmatova, Gul'Naz Z.,Korshin, Dmitry E.,Gubaidullin, Aidar T.,Krivolapov, Dmitry B.,Rizvanov, Il'Dar Kh.,Bazanova, Olga B.,Sinyashin, Oleg G.,Latypov, Shamil K.
p. 13132 - 13145
(2018/10/31)
Regioselective Ring Expansion of Isatins with in Situ Generated α-Aryldiazomethanes: Direct Access to Viridicatin Alkaloids
A novel efficient one-pot regioselective ring-expansion reaction of isatins with in situ generated α-aryl/heteroaryldiazomethanes for the construction of viridicatin alkaloids has been described under metal-free conditions. The utility of this protocol is further demonstrated in the synthesis of naturally occurring viridicatin, viridicatol, and substituted 3-O-methyl viridicatin and their scale up.
A concise and versatile synthesis of viridicatin alkaloids from cyanoacetanilides
The efficient synthesis of 3-hydroxy-4-arylquinolin-2(1H)-ones through one-pot Knoevenagel condensation/epoxidation of cyanoacetanilides followed by decyanative epoxide-arene cyclization is described. A convergent assembly with functionalized aldehydes allows for rapid synthesis with diverse substitution patterns. Isolation of 3-hydroxy-4-arylquinolin-2(1H)-ones is readily accomplished by precipitation and filtration.
Kobayashi, Yusuke,Harayama, Takashi
supporting information; experimental part
p. 1603 - 1606
(2009/08/07)
Stereospecific synthesis of dl-cyclopenin and dl-cyclopenol.
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White,Haefliger,Dimsdale
p. 233 - 242
(2007/10/07)
Thermal degradation and mass spectrometry of benzodiazepine alkaloids (minus)-cyclopenin and (minus)-cyclopenol
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Luckner,Winter,Nover,Reisch
p. 2575 - 2588
(2007/10/04)
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