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NHC‐Catalyzed Benzylic C sp³ –H Bond Activation of Alkylarenes and N ‐Benzylamines for the Synthesis of 3 H ‐Quinazolin‐4‐ones: Experimental and Theoretical Study
Author(s) -
Alanthadka Anitha,
Devi E. Sankari,
Nagarajan Subbiah,
Sridharan Vellaisamy,
Suvitha Ambigapathy,
Maheswari C. Uma
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.201600792
Subject(s) - chemistry , carbene , nucleophile , catalysis , medicinal chemistry , oxidative addition , combinatorial chemistry , organic chemistry
An N‐heterocyclic carbene catalyzed benzylic C sp³ –H bond activation of alkylarenes and N ‐benzylamines under metal‐free conditions was developed. This organocatalyzed oxidative transformation afforded the corresponding carbonyl derivatives in good to excellent yields. A variety of alkylarenes and N ‐benzylamines were tolerated under the optimized reaction conditions. The established method was further extended to the synthesis of biologically important 3 H ‐quinazolin‐4‐ones in good yields. For example, NPS 53574, a potent calcium receptor antagonist, was successfully synthesized by using this oxidative protocol. DFT studies show that the benzylic C–H bond activation proceeds through the nucleophilic attack of the free carbene on the benzylic carbon atom.