118520-79-9

Upstream product

• 33578-05-1 methyl 2-(phenylethynyl)benzoate 
• 110166-71-7 ethyl 2-(phenylethynyl)benzoate 
• 88-67-5 2-Iodobenzoic acid 
• 3930-83-4 o-iodobenzamide 
• 80221-08-5 2-(2-phenylethynyl)benzamide 
• 536-74-3 phenylacetylene 
• 294190-47-9 2-iodo-N-methoxy-N-methyl-benzamide 
• 294190-46-8 N-methoxy-N-methyl-2-(2-phenylethynyl)benzamide 
• 610-97-9 o-iodo-methyl-benzoic acid 
• 88180-65-8 isopropyl 2-(2-phenylethynyl)benzoate 
• 494747-17-0 tert-butyl 2-(phenylethynyl)benzoate 

Downstream Products

• 4809-08-9 3-phenyl-isocoumarin 
• 95161-79-8 3-phenyl-4-(p-tolyl)-1H-isochromen-1-one 

Relevant academic research and scientific papers

Regioselective Synthesis of 4-Aryl-1,3-dihydroxy-2-naphthoates through 1,2-Aryl-Migrative Ring Rearrangement Reaction and their Photoluminescence Properties

4-Aryl-1,3-dihydroxy-2-naphthoates having the less accessible 1,2,3,4-tetrasubstituted naphthalene scaffold and that show photoluminescence emission from solid state as well as in solutions, were selectively synthesized from brominated lactol silyl ethers

Synthesis of 4-chloroisocoumarins via intramolecular halolactonization of o-alkynylbenzoates: PhICl2-mediated C-O/C-Cl bond formation

A series of 4-chloroisocoumarins were conveniently synthesized from o-alkynylbenzoates via PhICl2-mediated intramolecular cyclization under metal-free conditions. PhICl2 plays the role of both the oxidant and the chlorine source to e

Metal-Free Synthesis of 4-Chloroisocoumarins by TMSCl-Catalyzed NCS-Induced Chlorinative Annulation of 2-Alkynylaryloate Esters

4-Chloroisocoumarins can be conveniently prepared from 2-alkynylaryloate esters via the activation of alkynes by electrophilic chlorine, generated in situ from N-chlorosuccinimide (NCS) in the presence of 10 mol % trimethylsilyl chloride (TMSCl), which leads to 6-endo-dig-selective chlorinative annulation to give the desired products in moderate to quantitative yields. The procedure employs readily available reagents and can be conveniently carried out on a wide scope of substrates under mild conditions (0 °C to rt). Furthermore, the reaction is scalable for gram-scale preparation of 4-chloroisocoumarins. Additionally, 4-bromo- and 4-iodoisocoumarins can be prepared in moderate to good yields by replacing NCS with N-bromosuccinimide (NBS) and N-iodosuccinimide (NIS), respectively.

Generation of 4-iodoisocoumarins through a TBAI-mediated oxidative cyclization of 2-alkynoates

A tetra-butylammonium iodide (TBAI)-mediated oxidative iodocyclization of 2-alkynoates for the synthesis of various 4-iodoisocoumarin is described herein, and the reaction is highly efficient and shows broad functional group tolerance. This newly develope

Synthesis of benzil-o-carboxylate derivatives and isocoumarins through neighboring ester-participating bromocyclizations of o-alkynylbenzoates

Bromide mediated neighboring ester-participating bromocyclizations of o-alkynylbenzoates are described here for the synthesis of benzil-o-carboxylates. 4-bromoisocoumarins are also synthesized when phenyl o-alkynylbenzoate is used as the substrate. Mechanistic studies suggest that the whole process is composed of an electrophilic bromocyclization and a dibromohydration-based ring-opening, and the neighboring ester group participates in the bromocyclization. Interestingly, the two oxygen atoms of the keto carbonyls in benzil-o-carboxylates are both derived from water. The electrophilic bromo source is in situ generated from the oxidation of bromide.

Copper(II)chloride-mediated cyclization reaction of N-alkoxy- orthoalkynylbenzamides

A regioselective intramolecular cyclization/halogenation reaction of N-alkoxy-o-alkynylbenzamides with CuCl2/NCS was developed. The corresponding 3-(chloromethylene)isobenzofuran-1-ones were exclusively obtained via 5-exo-dig cyclization in moderate to excellent yields within 0.5-1 h. This approach has been successfully used to synthesize a biaryl compound by the Suzuki-Miyaura reaction.

Halocyclization of methyl 2-alkynylbenzoates to isocoumarins using cupric halides

Treatment of methyl 2-alkynylbenzoates with two to three equivalents of CuX2 (X = Cl or Br) in refluxing acetonitrile gave isocoumarins 2 in good to excellent chemical yields.

Cy2NH·HX-promoted cyclizations of o-(alk-1-ynyl)benzoates and (Z)-alk-2-en-4-ynoate with copper halides to synthesize isocoumarins and α-pyrone

Cy2NH·HX was found to improve the cyclization reactions of o-(alk-1-ynyl)benzoates and (Z)-alk-2-en-4-ynoate with CuX2 (X = Cl, Br) to synthesize the corresponding 4-haloisocoumarins and 5-bromo-2-pyrone, respectively. In the presenc

Organomercury Mediated Synthesis of Isocoumarins

A facile and convenient synthesis of isocoumarins via an organomercurial route is reported.The synthesis involves reaction of methyl 2-alkynbenzoates with mercuric acetate to give the corresponding isocoumarin mercurials which serve as intermediates to afford the appropriate isocoumarins having substituents as Cl,I,Br,COCH3 etc.