14166-16-6

Upstream product

• 873-73-4 4-n-chlorophenylacetylene 
• 613-84-3 2-hydroxy-5-methylbenzaldehyde 
• 104-88-1 4-chlorobenzaldehyde 
• 1450-72-2 5-methyl-2-hydroxyacetophenone 
• 16635-10-2 1-(p-chlorophenyl)-3-(2-hydroxy-5-methylphenyl)prop-1-en-3-one 
• 75227-44-0 2'-Hydroxy-5'-methyl-4-chlorochalkone α,β-dibromide 

Downstream Products

• 60402-30-4 2-(4-chlorophenyl)-6-methyl-4H-chromen-4-one 
• 130252-76-5 3-(4-chlorophenyl)-6-methyl-4H-chromen-4-one 
• 73110-60-8 C₁₆H₁₅ClO 
• 1266399-37-4 4-(4-chlorophenyl)-8-methyl-4H-chromeno[4,3-d][1,2,3]selenadiazole 
• 1266399-49-8 C₁₇H₁₆ClN₃O₂ 

Relevant academic research and scientific papers

Organocatalytic Approach for Assembling Flavanones via a Cascade 1,4-Conjugate Addition/oxa-Michael Addition between Propargylamines with Water

A DBU-catalyzed one-pot cascade reaction of propargylamines and water for the synthesis of flavanones has been developed. This process proceeds via a sequence of 1,4-conjugate addition of water to alkynyl o-quinone methide (o-AQM), followed by the alkyne-allene isomerization and subsequent intramolecular oxa-Michael addition. This strategy provides a convenient method for accessing a broad range of flavanones in good to excellent yields with good functional-group tolerance, in particular, the reactive halo functional groups.

Mild and efficient one-pot synthesis of diverse flavanone derivatives via an organocatalyzed Mannich-type reaction

A facile ethylenediamine diacetate (EDDA)-catalyzed one-pot synthesis of biologically interesting flavanone derivatives from 2-hydroxyacetophenones, aromatic aldehydes, and aniline via a Mannich-type reaction is described. This synthetic method provides a rapid access to biologically interesting flavanone derivatives. To demonstrate this method, several biologically interesting natural products bearing a flavanone moiety were synthesized as racemates.

Simple and efficient one step synthesis of functionalized flavanones and chalcones

A facile and highly efficient microwave-assisted synthesis of functionalized chalcones and flavanones based on the Claisen-Schmidt condensation reaction is reported. The method describes the synthesis of flavanones in single step with excellent yield and it was revealed that position and number of substituents on acetophenones and aromatic aldehydes played a very crucial and key role in the construction of flavanone derivatives. Among the thirty two synthesized compounds, five chalcones and one flavanone were novel compounds.

Synthesis and cytotoxic activity of 4-aryl-4H-chromeno[4,3-d] [1,2,3] selenadiazoles

Fourteen 4-Aryl-4H-chromeno[4,3-d][1,2,3] selenadiazole derivatives were synthesized by the reaction of fla-vonone-4-semicarbazones with SeO2. The structures of the target compounds 1a-n were elucidated by 1H NMR, IR spectra, ESI-MS and elemental analyses. The preliminary cytotoxic activities of 1a-n against K562, KB, A549, SMC-7721 and SGC-7901 cell lines were evaluated by MTT method, indicating that most compounds displayed moderate to good antiproliferative activities against K562 and KB cell lines. Compounds 1m and 1n, the most potent ones, were promising template for development of novel potent antitumor agents.

Reaction of 2'-Hydroxychalcone Dibromides with Me2SO

2'-Hydroxychalcone dibromides on treatment with Me2SO gave 2'-hydroxychalcone, 2'-hydroxy-3'- or 2'-hydroxy-5'-bromochalcone, flavone, monobrominated flavone, 6,8-dibromoflavone, 3-bromoflavone, and 3-, 6-, or 8-dibromoflavone.