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. 2017 Jan 6;19(1):150-153.
doi: 10.1021/acs.orglett.6b03455. Epub 2016 Dec 21.

Iodocyclization of N-Arylpropynamides Mediated by Hypervalent Iodine Reagent: Divergent Synthesis of Iodinated Quinolin-2-ones and Spiro[4,5]trienones

Ying Zhou  1 , Xiang Zhang  1 , Yong Zhang  1 , Linxin Ruan  1 , Jiacheng Zhang  2 , Daisy Zhang-Negrerie  1 , Yunfei Du  1
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Iodocyclization of N-Arylpropynamides Mediated by Hypervalent Iodine Reagent: Divergent Synthesis of Iodinated Quinolin-2-ones and Spiro[4,5]trienones

Ying Zhou et al. Org Lett. .

Abstract

PhI(OCOCF3)2 acts as both a nonmetal oxidant and an iodination reagent to trigger iodocyclization of N-arylpropynamides while selectively affording iodinated quinolin-2-ones or the spiro[4,5]trienone skeleton, depending on the substituent pattern. In cases where the N-arylpropynamide bears a para-fluorine on the aniline ring, the spiro compound is formed via an exclusive defluorination process; otherwise, the product was quinolin-2-one.

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