65131-08-0

Upstream product

• 16859-59-9 3-hydroxy-1(3H)-isobenzofuranone 
• 51287-54-8 3-(phenylsulfanyl)isobenzofuran-1(3H)-one 
• 4122-56-9 methyl o-formylbenzoate 
• 108-98-5 thiophenol 
• 119-67-5 o-carboxybenzaldehyde 

Downstream Products

• 7336-64-3 1-hydroxy-4-methoxyanthracene-9,10-dione 
• 176516-27-1 5,10-dihydroxy-11H-benzo[b]fluoren-11-one 
• 81-64-1 1,4-dihydroxy-9,10-anthracenedione 
• 1021499-77-3 ethyl 3-(2-phenylsulfonylmethylphenyl)-1,4-dihydroxynaphthalene-2-carboxylate 
• 1021499-82-0 methyl 12-hydroxy-6-oxo-6H-dibenzo[c,h]chromen-11-carboxylate 
• 24137-11-9 ethyl 1,4-dioxo-1,4-dihydronaphthalen-2-ylcarbamate 
• 2348-77-8 2-phenyl[1,4]naphthoquinone 
• 60544-07-2 2-(4-methoxyphenyl)naphthalene-1,4-dione 
• 60544-08-3 2-(4-methylphenyl)naphthalene-1,4-dione 
• 59962-62-8 2-(4-chlorophenyl)naphthalene-1,4-dione 
• 65490-97-3 1,2′-binaphthyl-1′,4′-dione 

Relevant academic research and scientific papers

Strategies towards potent trypanocidal drugs: Application of Rh-catalyzed [2?+?2?+?2] cycloadditions, sulfonyl phthalide annulation and nitroalkene reactions for the synthesis of substituted quinones and their evaluation against Trypanosoma cruzi

Rhodium-catalyzed [2 + 2 + 2] cycloadditions, sulfonyl phthalide annulations and nitroalkene reactions have been employed for the synthesis of 56 quinone-based compounds. These were evaluated against Trypanosoma cruzi, the parasite that causes Chagas disease. The reactions described here are part of a program that aims to utilize modern, versatile and efficient synthetic methods for the one or two step preparation of trypanocidal compounds. We have identified 9 compounds with potent activity against the parasite; 3 of these were 30-fold more potent than benznidazole (Bz), a drug used for the treatment of Chagas disease. This article provides a comprehensive outline of reactions involving over 120 compounds aimed at the discovery of new quinone-based frameworks with activity against T. cruzi.

Hauser–Kraus Annulation of Phthalides with Nitroalkenes for the Synthesis of Fused and Spiro Heterocycles

Hauser–Kraus annulation of sulfonylphthalides with simple conjugated nitroalkenes follows the expected pathway to furnish naphthoquinones in moderate yields. However, a strategic variation of this reaction by employing nitroalkenes bearing an additional nucleophilic site results in [4+4] annulation leading to complex fused and spiro heterocycles in high yields with high selectivity through a cascade process involving Michael addition, Dieckmann cyclization, and a series of eliminations and rearrangements.

Tandem reversible addition-intramolecular lactonization for the synthesis of 3-functionalized phthalides

A new tandem process based on reversible nucleophilic addition and intramolecular lactonization of methyl 2-formylbenzoate leads to the efficient synthesis of 3-functionalized phthalides, which are important precursors for the synthesis of quinone skeletons via Hauser-Kraus annulation. The reactions are successfully carried out under mild conditions in single operations.

A new entry for the preparation of substituted aromatic carbonyl compounds mediated by Samarium(II) iodide

A new route to substituted aromatic lactones and lactams via SMI2-promoted desulfurization is described. Direct replacement of the phenylthio substituent by hydroxyalkylated groups featuring the novel accessible process for the construction of continuous quaternary carbon centers could be accomplished when the same type of reactions was undertaken with carbonyl compounds in the presence of SmI2.

Boron Trifluoride Promoted Reaction of Arenesulfinic Acids with Phthalaldehydic Acids: Enroute to 3-Arylsulfonyl Phthalides

The reaction of arenesulfinic acids 4 with phthalaldehydic acids 2 in the presence of boron trifluoride provides a practicable synthetic procedure for the preparation of 3-arylsulfonyl phthalides.