Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2008(7): 1078-1084
DOI: 10.1055/s-2008-1032125
DOI: 10.1055/s-2008-1032125
PAPER
© Georg Thieme Verlag Stuttgart · New York
Reaction of Huisgen Zwitterion with Diaryl Ketones Leading to the Facile Synthesis of Mono- and Bis(alkoxycarbonyl)hydrazones
Further Information
Received
16 August 2007
Publication Date:
06 March 2008 (online)
Publication History
Publication Date:
06 March 2008 (online)

Abstract
The Huisgen zwitterion, generated from triphenylphosphine and dialkyl azodicarboxylates, afforded upon reaction with diaryl ketones both mono- and bis(alkoxycarbonyl)hydrazones, depending on the reaction conditions.
Key words
Huisgen zwitterion - diaryl ketones - azo compounds - esters - hydrazones
- For reviews, see:
-
1a
Methot JL.Roush WR. Adv. Synth. Catal. 2004, 346: 1035 -
1b
Lu X.Zhang C.Xu Z. Acc. Chem. Res. 2001, 34: 535 -
1c
Nair V.Menon RS.Sreekanth AR.Abhilash N.Biju AT. Acc. Chem. Res. 2006, 39: 520 -
2a
Brunn E.Huisgen R. Angew. Chem., Int. Ed. Engl. 1969, 8: 513 -
2b
Huisgen R. In The Adventure Playground of Mechanisms and Novel Reactions: Profiles, Pathways and DreamsSeeman JI. American Chemical Society; Washington DC: 1994. p.62 ; and references cited therein -
3a
Mitsunobu O. Synthesis 1981, 1 -
3b
Hughes DL. Org. Prep. Proced. Int. 1996, 28: 127 -
3c
Watanabe T.Gridnave ID.Imamoto T. Chirality 2000, 12: 346 - 4
Otte RD.Sakata T.Guzei IA.Lee D. Org. Lett. 2005, 7: 495 - 5
Girard M.Murphy P.Tsou NN. Tetrahedron Lett. 2005, 46: 2449 -
6a
Nair V.Biju AT.Vinod AU.Suresh E. Org. Lett. 2005, 7: 5139 -
6b
Nair V.Biju AT.Mohanan K.Suresh E. Org. Lett. 2006, 8: 2213 -
6c
Nair V.Mathew SC.Biju AT.Suresh E. Angew. Chem. Int. Ed. 2007, 46: 2070 -
6d
Nair V.Biju AT.Abhilash KG.Menon RS.Suresh E. Org. Lett. 2005, 7: 2121 -
7a
Nair V.Biju AT.Mathew SC. Synthesis 2007, 697 -
7b
Liu Y.Xu C.Liu L. Synthesis 2003, 1335 - 8
Nair V.Rajesh C.Vinod AU.Bindu S.Sreekanth AR.Mathen JS.Balagopal L. Acc. Chem. Res. 2003, 36: 899 - 11
Keith JM.Gomez L. J. Org. Chem. 2006, 71: 7113 -
12a
Haddad N.Baron J. Tetrahedron Lett. 2002, 43: 2171 -
12b
Dabiri M.Salehi P.Bagbanzadeh M.Bahramnejad M. Tetrahedron Lett. 2006, 47: 6983
References
The crystal structure data of compound 5b have been deposited at the Cambridge Crystallographic Data Centre and allocated the reference no. CCDC 650903.
10The crystal structure data of compound 6d have been deposited at the Cambridge Crystallographic Data Centre and allocated the reference no. CCDC 650904.