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

Tuan Thanh Dang; Tung Thanh Dang; Peter Langer

doi:10.1055/s-0031-1289550

ACCOUNT

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

Tuan Thanh Dang^a,b, Tung Thanh Dang^a, 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;

Abstract

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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

Volltext

Referenzen

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