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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.