Next Article in Journal
A Recyclable Nanoparticle-Supported Rhodium Catalyst for Hydrogenation Reactions
Previous Article in Journal
Homoisoflavanones from Agave tequilana Weber
Molecules 2010, 15(5), 3302-3310; doi:10.3390/molecules15053302
Article

Efficient Routes to Pyrazolo[3,4-e][1,2,4]triazines and a New Ring System: [1,2,4]Triazino[5,6-d][1,2,3]triazines

1,* , 2
, 1 and 1
Received: 24 December 2009; in revised form: 15 March 2010 / Accepted: 23 April 2010 / Published: 4 May 2010
Download PDF [172 KB, uploaded 18 June 2014]
Abstract: Arylhydrazonomalononitriles 1a,b react with phenylhydrazine to yield amidrazones 2a,b that cyclize to give 2-aryl-5-phenylhydrazono-2,5-dihydro-[1,2,4]-triazine-6-carbonitriles 5a,b upon reaction with dimethylformamide dimethylacetal (DMFDMA). Refluxing 5a,b in glacial acetic acid resulted in the formation of the pyrazolo-1,2,4-triazines 6a,b. Compounds 6a,b were also formed upon treatment of 3-amino-4-phenylhydrazono-1-phenyl-2-pyrazolin-5-ones 7a,b with DMFDMA. Reacting these triazinyl arylhydrazononitriles 5a,b with hydroxylamine hydrochloride in ethanolic sodium acetate afforded amidrazones 8a,b that are readily cyclized in refluxing dimethylformamide into [1,2,4]triazino[1,2,3]triazines 10a,b.
Keywords: amidrazones; arylhydrazononitrile; amidoximes; [1,2,4]triazino[1,2,3]triazine; dimethylformamide; dimethylacetal; pyrazolo[1,2,4]triazine amidrazones; arylhydrazononitrile; amidoximes; [1,2,4]triazino[1,2,3]triazine; dimethylformamide; dimethylacetal; pyrazolo[1,2,4]triazine
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Export to BibTeX |
EndNote


MDPI and ACS Style

Al-Matar, H.M.; Khalil, K.D.; Al-Dorri, D.M.; Elnagdi, M.H. Efficient Routes to Pyrazolo[3,4-e][1,2,4]triazines and a New Ring System: [1,2,4]Triazino[5,6-d][1,2,3]triazines. Molecules 2010, 15, 3302-3310.

AMA Style

Al-Matar HM, Khalil KD, Al-Dorri DM, Elnagdi MH. Efficient Routes to Pyrazolo[3,4-e][1,2,4]triazines and a New Ring System: [1,2,4]Triazino[5,6-d][1,2,3]triazines. Molecules. 2010; 15(5):3302-3310.

Chicago/Turabian Style

Al-Matar, Hamad Mohamed; Khalil, Khaled Dessouky; Al-Dorri, Doa’a Mohamed; Elnagdi, Mohamed Helmy. 2010. "Efficient Routes to Pyrazolo[3,4-e][1,2,4]triazines and a New Ring System: [1,2,4]Triazino[5,6-d][1,2,3]triazines." Molecules 15, no. 5: 3302-3310.


Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert