Synthesis of Antipyrine Derivatives Derived from Dimedone

Coupling of dimedone with the diazonium salt of 4-aminoantipyrine afforded 2,3-dimethyl-4-[2-（5,5-dimethyl- 2,6-dioxocyclohex-2-ylidend）-hydrazino]-5-oxo-1-phenylpyrazoline （3）. Reaction of 3 with excess phenylhydrazine gave the mixed trishydrazone derivative 4. Treatment of 3 with hydroxylamine pro...

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Bibliographic Details
Published in:	Chinese journal of chemistry Vol. 25; no. 4; pp. 570 - 573
Main Authors:	Ei ashry, E. S. H., Awad, L. F., Ibrahim, E. I., Bdeewy, O. Kh
Format:	Journal Article
Language:	English
Published:	Weinheim WILEY-VCH Verlag 01-04-2007 WILEY‐VCH Verlag
Subjects:	1,2,3‐triazole 3-triazole antipyrine dimedone phenylhydrazone 双甲酮安替比林衍生物
Online Access:	Get full text
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Summary:	Coupling of dimedone with the diazonium salt of 4-aminoantipyrine afforded 2,3-dimethyl-4-[2-（5,5-dimethyl- 2,6-dioxocyclohex-2-ylidend）-hydrazino]-5-oxo-1-phenylpyrazoline （3）. Reaction of 3 with excess phenylhydrazine gave the mixed trishydrazone derivative 4. Treatment of 3 with hydroxylamine produced the bisoxime 5 which upon dehydrative cyclization with acetic anhydride gave the corrsponding tetrahydrobenzo[d][1,2,3]triazole derivative 7. A one-pot synthesis of 7 was done by reacting 3 with hydroxylamine hydrochloride in pyridine, followed by heatment with acetic anhydride.
Bibliography:	31-1547/O6 O626.21 dimedone, antipyrine, 1,2,3-triazole, phenylhydrazone ark:/67375/WNG-4XM1534F-X ArticleID:CJOC200790107 istex:7B9EAA6C25AA157E3A4A53F27E0D3E057033AD78 00203‐4271360
ISSN:	1001-604X 1614-7065
DOI:	10.1002/cjoc.200790107