Cascade S N 2′–S N Ar, Elimination, and 1,5‐Hydride Shift Reactions by Acetylacetone/Acetoacetic Esters: Synthesis of 9,10‐Dihydroacridines

A reaction involving the use of acetylacetone/methyl acetoacetate and Morita–Baylis–Hillman acetates for the efficient, one‐pot, metal‐free synthesis of 9,10‐dihydroacridines at room temperature was developed. The cascade of reactions involved sequential S N 2′–S N Ar reactions, elimination, and red...

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Veröffentlicht in:European journal of organic chemistry 2016-10, Vol.2016 (29), p.4981-4984
Hauptverfasser: Gupta, Tanu, Bharadwaj, Kishor Chandra, Singh, Radhey M.
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container_title European journal of organic chemistry
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creator Gupta, Tanu
Bharadwaj, Kishor Chandra
Singh, Radhey M.
description A reaction involving the use of acetylacetone/methyl acetoacetate and Morita–Baylis–Hillman acetates for the efficient, one‐pot, metal‐free synthesis of 9,10‐dihydroacridines at room temperature was developed. The cascade of reactions involved sequential S N 2′–S N Ar reactions, elimination, and reduction through ketene generation and hydride transfer. Evidence for hydride shift via a ketene intermediate was also discussed.
doi_str_mv 10.1002/ejoc.201600911
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title Cascade S N 2′–S N Ar, Elimination, and 1,5‐Hydride Shift Reactions by Acetylacetone/Acetoacetic Esters: Synthesis of 9,10‐Dihydroacridines
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