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Synthesis 2004(17): 2877-2885  
DOI: 10.1055/s-2004-834882
PAPER
© Georg Thieme Verlag Stuttgart · New York

Efficient Syntheses of 3-(3-Arylsydnon-4-yl)triazole Derivatives

Mei-Hsiu Shih*a, Mou-Yung Yehb, Mei-Jin Leeb, Yu-Sheng Sua
a Department of Chemical Engineering, Southern Taiwan University of Technology, Tainan, Taiwan 710, R.O.C.
Fax: +886(6)2425741; e-Mail: meihsius@mail.stut.edu.tw;
b Department of Chemistry, National Cheng Kung University, Tainan, Taiwan 701, R.O.C.
Further Information

Publication History

Received 7 June 2004
Publication Date:
21 October 2004 (online)

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Abstract

3-Arylsydnone-4-carbohydroximic acid chlorides 1 were reacted with hydrazine hydrate to give hydrazino(3-arylsydnon-4-yl)methanone oximes 2 which are good precursors of 4-tri­azolyl sydnones. 5-Aryl-3-(3-arylsydnon-4-yl)-1H-[1,2,4]triazoles 4 could be synthesized in excellent yields by reacting hydrazino(3-arylsydnon-4-yl)methanone oximes 2 with aromatic aldehydes 3 under acid catalysis. Compounds 2 were also reacted with 3-aryl-4-formylsydnones 5 and aliphatic aldehydes 7 to produce 3-(3-arylsydnon-4-yl)-5-(3-arylsydnon-4-yl)-1H-[1,2,4]triazoles 6 and 5-alkyl-3-(3-arylsydnon-4-yl)-1H-[1,2,4] triazoles 8, respectively.

Key words

3-arylsydnone-4-carbohydroximic acid chlorides - hydrazino(3-arylsydnon-4-yl)methanone oximes - 5-aryl-3-(3-arylsydnon-4-yl)-1H-[1,2,4]triazoles - 3,5-disydnonyl triazole derivatives - 5-alkyl-3-sydnonyl triazoles

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Further details have been deposited at the Cambridge Crystallographic Data Centre and allocated the deposition numbers CCDC 240270 and CCDC 240271, respectively.

31

X-ray analytical data are listed in Table [2] . Further details have been deposited at the Cambridge Crystallographic Data Centre under deposition number CCDC 240272.