Competitive cascade cyclization of 2′-tosyloxychalcones: An easy access to thioflavones and thioaurones

A new and efficient approach for the synthesis of thioflavones and thioaurones by competitive cascade cyclization of 2′-tosyloxychalcones has been developed. 2′-Tosyloxychalcones were smoothly converted into thioflavones and thioaurones by incorporation of sulfur atom using elemental sulfur and trie...

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Bibliographic Details
Published inSynthetic communications Vol. 50; no. 15; pp. 2347 - 2354
Main Authors Venkateswarlu, Somepalli, Murty, Gandrotu Narasimha, Satyanarayana, Meka, Siddaiah, Vidavalur
Format Journal Article
LanguageEnglish
Published PHILADELPHIA Taylor & Francis 02.08.2020
Taylor & Francis Ltd
Subjects
2′-tosyloxychalcone
Chemistry
Chemistry, Organic
Cyclization
Functional groups
Physical Sciences
Science & Technology
Substrates
Sulfur
thioaurone
thioflavone
Triethylamine
2 '-tosyloxychalcone
ISOAURONES
HETEROCYCLIC-ANALOGS
MECHANISM
HEMITHIOINDIGO
4H-1-BENZOTHIOPYRAN-4-ONES
thioaurone
thioflavone
Cyclization
PHOTOSWITCHES
sulfur
INHIBITORS
DERIVATIVES
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Summary:A new and efficient approach for the synthesis of thioflavones and thioaurones by competitive cascade cyclization of 2′-tosyloxychalcones has been developed. 2′-Tosyloxychalcones were smoothly converted into thioflavones and thioaurones by incorporation of sulfur atom using elemental sulfur and triethylamine in DMSO with good yields. The advantages of the methodology are the formation of both thioflavones and thioaurones in a single step. Easily accessible substrates, mild reaction conditions and compatibility with a broad range of functional groups make this protocol clean and inexpensive.
ISSN:0039-7911
1532-2432
DOI:10.1080/00397911.2020.1775852