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Synthesis 2011(15): 2407-2414  
DOI: 10.1055/s-0030-1260101
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Iodocyclization of N-Aryl-3-phenylpropiolamides by I2/CAN: A Convenient Route for the Selective Synthesis of Quinolin-2-ones

Pravin R. Likhar*a, Shailesh S. Racharlawara, Manjusha V. Karkhelikara, M. S. Subhasa, B. Sridharb
a Inorganic and Physical Chemistry Division, Indian Institute of Chemical Technology, Hyderabad 500007, India
b X-ray Crystallography Center, Indian Institute of Chemical Technology, Hyderabad 500007, India
Fax: +91(40)27160921; e-Mail: plikhar@iict.res.in;
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Publication History

Received 28 February 2011
Publication Date:
08 July 2011 (online)

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Abstract

A general method has been developed for the selective synthesis of 3-iodoquinolin-2-ones and spiro[4.5]trienes via intramolecular iodocyclization of N-(ortho-substituted aryl)-3-phenylpropiolamides using iodine/cerium(IV) ammonium nitrate reagent under mild reaction conditions. The electronic effect of ortho-substituents (electron-rich and electron-deficient group) triggers the two different reaction pathways resulting to iodocyclized quinolin-2-one and ipso-iodocyclized spiro-type compounds.

Key words

iodocyclization - quinolin-2-ones - alkynes - heterocycles - spiro compounds

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