Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 86, Issue 20, Pages 14016-14027Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.1c00271
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- Coordenacao de Aperfeicoamento de Pessoal de Nivel Superior - Brasil (CAPES) [001]
- FAPERGS [PqG 19/25510001867-3]
- CNPq
- FINEP
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A new method for the synthesis of 4-chalcogenyl-1H-isochromen-1-ones was developed using ultrasound irradiation, achieving high yields of the target compounds in a short period of time.
A new method was developed for the synthesis of 4-chalcogenyl-1H-isochromen-1-ones through the 6-endo-dig electrophilic cyclization of 2-alkynylaryl esters and diorganyl dichalcogenides under ultrasound irradiation. The reactions were performed under mild conditions, using Oxone as a green oxidant to promote the cleavage of the chalcogen-chalcogen bond in diorganyl diselenides and ditellurides to generate electrophilic species in situ. A total of 25 compounds were selectively obtained after 30-70 min, in good to excellent yields (74-95%). This procedure was extended to prepare 5H-selenopheno[3,2-c]isochromen-5-ones. Additionally, for the first time, the 4-chalcogenyl-1H-isochromen-1-ones were used as substrates in the thionation reaction, using Lawesson's reagent and microwave irradiation under solvent-free conditions, obtaining the thio derivatives in yields of up to 99% in only 15 min.
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