Synthesis 2007(5): 697-704  
DOI: 10.1055/s-2007-965910
PAPER
© Georg Thieme Verlag Stuttgart · New York

The Reaction of Huisgen Zwitterion with Diaryl-1,2-diones and Ketones: An Efficient Protocol for Carbon-Nitrogen Bond Formation

Vijay Nair*, A. T. Biju, Smitha C. Mathew
Organic Chemistry Section, Regional Research Laboratory (CSIR), Trivandrum 695019, India
Fax: +91(471)2491712; e-Mail: vijaynair_2001@yahoo.com;
Further Information

Publication History

Received 19 October 2006
Publication Date:
25 January 2007 (eFirst)

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Abstract

The reaction of Huisgen zwitterion, derived from triphenylphosphine and dialkyl azodicarboxylate, with diaryl-1,2-diones afforded N,N-dicarboalkoxy monohydrazones via a mechanistically novel rearrangement. Cyclic and acyclic ketones furnished vinyl hydrazinedicarboxylates under similar conditions.

Key words

betaines - diazo compounds - hydrazones - ketones - rearrangements

    References

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  • 2b

    The reaction of PPh3 and DEAD with dimethyl acetylenedicarboxylate affording pyrazoles is mentioned; rationalization of this reaction as occurring via the zwitterion 3 was provided by Huisgen (Ref. 3a).

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12

It may be mentioned that the mechanism presented herein is identical to that suggested by Liu and Lee (references 6 and 9, respectively).