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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Design, synthesis and application of spiro[4.5]cyclohexadienones via one-pot sequential
Vaibhav B Patil1, Jagadeesh Babu Nanubolu2, Rambabu Chegondi1
1Department of Organic Synthesis and Process Chemistry, CSIR-Indian Institute of Chemical Technology (CSIR-IICT), Hyderabad 500007, India. rchegondi@iict.res.in/cramhcu@gmail.com and Academy of Scientific and Innovative Research (AcSIR), Ghaziabad 201002, India.
Abstract:
One-pot sequential p-hydroxybenzylation/oxidative dearomatization/spiroannulation has been designed for the efficient construction of tetrahydrofuran containing spiro-cyclohexadienones. This reaction proceeds through the p-hydroxybenzylation of 1,3-diketones with p-hydroxybenzyl alcohol via quinone methide formation followed by oxidative dearomatization/spiroannulation with suitable alcohols. The Friedel-Crafts alkylation of spiro[4.5]cyclohexadienones with indoles provided a broad array of highly diastereoselective C-3 alkylated spirocycles and cyclohepta[b]indoles depending upon the ring size of the fused cyclic ketones.
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