Synthesis of a 7-azaindole by chichibabin cyclization: reversible base-mediated dimerization of 3-picolines.

The Journal of Organic Chemistry
Yun MaDavid B Collum

Abstract

The lithium diisopropylamide (LDA)-mediated condensation of 2-fluoro-3-picoline and benzonitrile to form 2-phenyl-7-azaindole via a Chichibabin cyclization is described. Facile dimerization of the picoline via a 1,4-addition of the incipient benzyllithium to the picoline starting material and fast 1,2-addition of LDA to benzonitrile cause the reaction to be complex. Both adducts are shown to reenter the reaction coordinate to produce the desired 7-azaindole. The solution structures of the key intermediates and the underlying reaction mechanisms are studied by a combination of IR and NMR spectroscopies.

References

Mar 28, 2007·Angewandte Chemie·David B CollumAntonio Ramirez
Apr 24, 2007·Journal of Medicinal Chemistry·Carlos Pérez-BaladoAngel R de Lera
Jun 20, 2007·Chemical Society Reviews·Jinhua J SongChris H Senanayake
Jun 20, 2007·Chemical Society Reviews·Manfred Schlosser, Florence Mongin
Jul 28, 2007·The Journal of Organic Chemistry·Anne SeggioFlorence Mongin

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Citations

Feb 19, 2013·Journal of the American Chemical Society·Timothy S De VriesDavid B Collum
Apr 4, 2017·The Journal of Organic Chemistry·Russell F AlgeraDavid B Collum
Jun 17, 2015·Chemical Communications : Chem Comm·Yechan Kim, Sungwoo Hong
Apr 30, 2010·The Journal of Organic Chemistry·Mohamed AbboudYves Fort
Oct 9, 2019·The Journal of Organic Chemistry·Julia V VyalyhSergey V Kurbatov
Sep 28, 2017·Journal of the American Chemical Society·Russell F AlgeraDavid B Collum

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