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

Gupta Tanu | Zendy; Bharadwaj Kishor Chandra | Zendy; Singh Radhey M. | Zendy

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

Author(s) -

Gupta Tanu,

Bharadwaj Kishor Chandra,

Singh Radhey M.

Publication year - 2016

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.201600911

Subject(s) - chemistry , acetylacetone , ketene , hydride , ethyl acetoacetate , reductive elimination , medicinal chemistry , cascade reaction , organic chemistry , metal , catalysis

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.

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