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Access to Methylidene-Azaspiro[4.5]decatrienones via Radical-Promoted Domino Thio-Functionalization/Dearomative
Chada Raji Reddy1,2, Puthiya Purayil Vinaya1,2, Ejjirotu Srinivasu1
1Department of Organic Synthesis & Process Chemistry CSIR-Indian Institute of Chemical Technology (CSIR-IICT), Hyderabad 500007, India.
Abstract:
An unprecedented approach involving radical-mediated sulfonylation/dearomative ipso-annulation of N-(methyl-2-phenylacetate)propiolamides using arylsulfonyl radical, generated from aryl diazonium salt in the presence of DABSO, is developed. This strategy provides uniquely substituted 3-sulfonyl azaspiro[4.5]decatrienones in good yields. The developed approach has also been extended fruitfully to 3-thiocyano aza-spirocycles through domino thiocyanation/dearomative ipso-annulation.
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