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Synlett 2011(18): 2633-2642  
DOI: 10.1055/s-0031-1289550
ACCOUNT
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Functionalized Heterocycles by Cyclization Reactions of Oxime and Hydrazone 1,4-Dianions

Tuan Thanh Danga,b, Tung Thanh Danga, Peter Langer*a,c
a Institut für Chemie, Universität Rostock, Albert-Einstein-Str. 3a, 18059 Rostock, Germany
b Vietnamese Academy of Science and Technology, 18 Hoang Quoc Viet, Hanoi, Vietnam
c Leibniz-Institut für Katalyse e.V. an der Universität Rostock, Albert-Einstein-Str. 29a, 18059 Rostock, Germany
Fax: +49(381)4986412; e-Mail: peter.langer@uni-rostock.de;
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Publikationsverlauf

Received 1 June 2011
Publikationsdatum:
25. Oktober 2011 (online)

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Abstract

Oxime and hydrazone 1,4-dianions can be generated in situ by deprotonation with 2 equivalents of n-butyllithium (n-BuLi) or lithium diisopropylamide (LDA). In this account, the development and synthetic applications of one-pot cyclizations of oxime and hydrazone dianions with various electrophiles are highlighted. These reactions provide an efficient synthesis of functionalized isoxazoles, pyrazoles and other heterocycles.

1 Introduction

2 Cyclization Reactions of Oxime 1,4-Dianions

3 Cyclization Reactions of Hydrazone 1,4-Dianions

4 Conclusion

Key words

cyclization - dianions - oximes - hydrazones - pyrazoles - isoxazoles

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