The method has the advantages of obtaining a target product through simple processing, providing a good method for synthesizing polysubstituted, particularly 2 and 3 position synchronously substituted fluorine-containing indole derivatives, along with simple operation, readily available raw materials and implementation by common laboratory equipment.
The 5-fluoro-2-trifluoromethyl-3-methyl indole butyrate serving as an intermediate can continue to react to form essential amino acids such as tryptophan and the intermediate compound can be used for synthesizing a plurality 3- substituent-2- trifluoromethyl indole derivatives and performing the fluoridated modification of some indole derivatives having physiological activity, and particularly provides a convenient feasible way of introducing fluorine atoms onto benzene rings.
Larock indole synthesis - Wikipedia
A possible mechanism for formation of the [3+2] annulated product parallels what has been proposed previously in the literature (). First, immediately following formation of the benzyne, a negatively charged indole nucleophilically attacks the aryne, resulting in intermediate A. The newly formed aryl carbanion then intramolecularly attacks the neighboring ester, displacing a methoxy group, which can also aid in deprotonation of the indole starting material.
METHYL ~-PHENYLACETATE IN INDOLE SYNTHESIS V
Nitrogen-containing heterocycles exhibit a diverse array of favorable biological and pharmacological properties. The indole core, in particular, is the foundation for many well known medicinally active compounds. Convenient methods for constructing fused indoles are of great value to medicinal chemists., In addition, indolone derivatives possess potent biological activities. Thus, new methodologies for their synthesis contribute significantly to the pursuit of new drugs. Of considerable current interest to medicinal chemists is the synthesis of new drug-like compounds in which two separate biologically interesting scaffolds, both independently known for their favorable activities, are fused., Since both indoles and indolones are relevent core structures for pharmaceuticals, a hybrid thereof could potentially lead to a series of biologically active compounds ().
The reaction of methyl indole-2-carboxylates and arynes affords a very efficient, high yielding synthesis of a novel indole-indolone ring system, which tolerates considerable functionality, is broad in scope and proceeds under mild reaction conditions.
Synthesis of 3-[(1-Aryl)aminomethyl]indoles | Request …
Moreover, coupling of 3-(3-methyl-1H-indol-2-yl)-3-oxopropanenitrile (2) with the diazonium salts of 3-phenyl-5-aminopyrazole 16 or 3-amino-1,2,4-triazole 17 gave the corresponding hydrazones 18 and 19, respectively.