Synthesis and reactions of 4,5-dihydro-4-oxo-pyrano [3,2-b]indole-3-carbaldehydes
The title substances 3 are accessible following two reaction pathes, beginning with the 1,3-dicarbonyl compounds I. The 2-amino-3-carbaldehydes 15 are synthesized from the oximes II. The reaction of 3 with β-amino crotonic esters yields a mixture of the 1
Gorlitzer,Michels
p. 106 - 115
(2007/10/02)
INTRODUCTION OF ACYL SUBSTITUTENTS AT POSITION 2 OF THE INDOLINONE RING
The acylation of 1-acetyl-3-indolinone at position 2 of the heterocycle was realized by the action of acetic and propionic anhydride in the presence of sulfuric acid.It was shown that the reaction takes place with a high yield through an O-acylation and a Fries rearrangement stage.The Fries rearrangement was used to convert the 1-acetyl-3-hydroxybenzoylindole into 1-acetyl-2-benzoyl-3-indolinone.The same β-diketone and also 1-acetyl-2-(p-chlorobenzoyl)-3-indolinone were obtained by the action of a mixture of acetic anhydride and sulfuric acid on the respective 1-acetyl-2-arylidene- 3-indolinones. 1-Acetyl-3-formyl-3-chloroindole was obtained by the reaction of 1-acetyl-3-indolinone with the Vilsmeier complex obtained from DMFA and phosphorus oxychloride.It was deacylated to 2-formyl-3-chloroindole.
Velezheva, V. S.,Smushkevich, V. Yu.,Romanova, O. B.,Kurkovskaya, L. N.,Suvorov, N. N.
p. 2186 - 2193
(2007/10/02)
Anellated chromones from heterocyclic 1,3 dicarbonyl compounds
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Goerlitzer
p. 523 - 539
(2007/10/08)
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