Category: phthalazines. I found the field of Chemistry very interesting. Saw the article Metal-free alkene carbooxygenation following tandem intramolecular alkoxylation/Claisen rearrangement: stereocontrolled access to bridged [4.2.1] lactones published in 2019.0, Reprint Addresses Ye, LW (corresponding author), Xiamen Univ, Coll Chem & Chem Engn, Key Lab Chem Biol Fujian Prov, State Key Lab Phys Chem Solid Surfaces, Xiamen 361005, Peoples R China.; Ye, LW (corresponding author), Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China.; Ye, LW (corresponding author), Nankai Univ, State Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R China.. The CAS is 62-23-7. Through research, I have a further understanding and discovery of 4-Nitrobenzoic acid.
Alkene carbooxygenation has attracted considerable attention over the past few decades as this approach provides an efficient access to various oxygen-containing molecules, especially the valuable O-heterocycles. However, examples of catalytic alkene carbooxygenation via a direct C-O cleavage are quite scarce, and the C-O cleavage in these cases is invariably initiated by transition metal-catalyzed oxidative addition. We report here a novel Bronsted acid-catalyzed intramolecular alkoxylation-initiated tandem sequence, which represents the first metal-free intramolecular alkoxylation/Claisen rearrangement. Significantly, an unprecedented Bronsted acid-catalyzed intramolecular alkene insertion into the C-O bond via a carbocation pathway was discovered. This method allows the stereocontrolled synthesis of valuable indole-fused bridged [4.2.1] lactones, providing ready access to biologically relevant scaffolds in a single synthetic step from an acyclic precursor. Moreover, such an asymmetric cascade cyclization has also been realized by employing a traceless chiral directing group. Control experiments favor the feasibility of a carbocation pathway for the process. In addition, biological tests showed that some of these newly synthesized indole-fused lactones exhibited their bioactivity as antitumor agents against different breast cancer cells, melanoma cells, and esophageal cancer cells.
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Reference:
Phthalazine – Wikipedia,
,Phthalazine | C8H6N2 – PubChem