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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
ipso-Cyclization of unactivated biaryl ynones leading to thio-functionalized spirocyclic enones
Chada Raji Reddy1, Uprety Ajaykumar1, Amol D Patil1
1Department of Organic Synthesis & Process Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad - 500007, India. rajireddy@iict.res.in.
Abstract:
Ceric ammonium nitrate (CAN)-promoted oxidative ipso-cyclization of unactivated biaryl ynones with S-centered radicals (SCN/SCF3) to access spiro[5,5]trienones has been established. This approach displayed excellent regioselectivity towards spirocyclization and tolerated a variety of functional groups. Dearomatization of hitherto unknown aryl/heteroaryl groups is also disclosed. DMSO is employed as a low-toxicity, inexpensive solvent as well as a source of oxygen.
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