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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 42, 2012 - Issue 22
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Original Articles

Catalysis by Lithium Perchlorate Enables Double-Conjugate Addition of Electron-Deficient Maleimides to 2-Aminopyridines and 2-Aminothiazoles

Tetiana Matviiuk Department of Chemistry, Kiev National Taras Shevchenko University, Kiev, UkraineCorrespondence[email protected]
,
Marian Gorichko Department of Chemistry, Kiev National Taras Shevchenko University, Kiev, Ukraine
,
Andriy Kysil Department of Chemistry, Kiev National Taras Shevchenko University, Kiev, Ukraine
,
Svitlana Shishkina Division of Functional Materials Chemistry, State Scientific Institution “Institute for Single Crystals” of National Academy of Science of Ukraine, Kharkiv, Ukraine
,
Oleg Shishkin Division of Functional Materials Chemistry, State Scientific Institution “Institute for Single Crystals” of National Academy of Science of Ukraine, Kharkiv, Ukraine; Department of Inorganic Chemistry, V. N. Karazin Kharkiv National University, Kharkiv, Ukraine
&
Zoia Voitenko Department of Chemistry, Kiev National Taras Shevchenko University, Kiev, Ukraine
Pages 3304-3310 | Received 04 Apr 2011, Published online: 18 Jul 2012
 
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Abstract

Lithium perchlorate has been found to catalyze the conjugate addition of maleimides with 2-aminopyridines and 2-aminothiazoles. The reaction proceeds under mild conditions leading to the corresponding double adducts in good yields. A plausible mechanism of this reaction has been proposed.

Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications ® to view the free supplemental file.

GRAPHICAL ABSTRACT

ACKNOWLEDGMENTS

We are grateful to Olexandr V. Turov, Magdalina D. Tsapko, and Olexandr Petin for help with NMR studies.

Notes

a For all products, the yields are given after recrystallization.

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