1215095-76-3

Upstream product

• 103-82-2 phenylacetic acid 
• 127-08-2 potassium acetate 
• 108-24-7 acetic anhydride 
• 57803-07-3 6,7-dimethyl-4-oxo-4H-chromene-3-carbaldehyde 

Downstream Products

• 1215095-92-3 8,9-dimethyl-5-ethoxy-3-phenyl-2H,5H-pyrano[3,2-c]chromen-2-one 

Relevant academic research and scientific papers

Synthesis of 3-phenyl-2H,5H-pyrano[3,2-c]chromen-2-one derivatives and their antineoplastic activity

Reaction of 4-oxo-4H-chromen-3-carbaldehydes 1 with phenylacetic acids 2 under mild conditions or microwave irradiation led to 3-phenyl-2-oxo-2H,5H- pyrano[3,2-c]chromen-5-yl acetates 3. At stronger conditions by-products 5-(2-hydroxybenzoyl)-3-phenyl-2H-pyran-2-ones 4 and 5-hydroxy-2H,10aH-pyrano[2, 3-b]chromen-2-ones 5 were also obtained. 5-Hydroxy- and 5-alkyloxy-2H,5H- pyrano[3,2-c]chromen-2-ones 6 and 7, respectively were easily prepared by reaction of 3 with water or alcohols. Twelve synthesized compounds were evaluated on their antineoplastic activities on 60 human tumour cell lines panels in NCI USA. According to the screening results 3-phenyl-2H,5H-pyrano[3,2- c]chromen-2-one was discovered as a new leading skeleton suitable for further development. Some SAR conclusions were made. Antitubuline mechanism for the most active compound 3g has been proposed. ARKAT USA, Inc.

A facile route to phenyl, phenylsulfanyl and phenylselanyl substituted pyrano[3,2-c]chromenes

The synthesis of phenyl, phenylsulfanyl and phenylselanyl substituted pyrano[3,2-c]chromenes 4 is accomplished via cyclocondensation of 4-oxo-4H-chromen-3-carbaldehydes 1 with appropriately substituted acetic acids 2 under mild conditions. Further treatment of 4 with alcohol or water led to 5-alkoxy- and 5-hydroxy-2H,5H-pyrano[3,2-c]chromen-2-ones 5 and 6, respectively. Acid and thermal catalysed rearrangement of 4-6 gave 5-hydroxypyrano[2,3-b]chromen-2(10aH)-ones 7 and their subsequent substitution led to 5-alkoxyderivatives 8. Reaction of 4 with amides led to 5-acylamino or 5-phenylsulfonamino substituted 2H,5H-pyrano[3,2-c]chromen-2-ones 9. Reactions were performed under heating or microwave irradiation.