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

doi:10.3390/molecules15053302

This article is

freely available
re-usable

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

Hamad Mohamed Al-Matar^1,* , Khaled Dessouky Khalil², Doa’a Mohamed Al-Dorri¹ and Mohamed Helmy Elnagdi¹

¹ Chemistry Department, Faculty of Science, University of Kuwait, P.O. Box 5969, Safat 13060, Kuwait ² Chemistry Department, Faculty of Science, Cairo University, Giza 12613, Egypt

* Author to whom correspondence should be addressed.

Received: 24 December 2009; in revised form: 15 March 2010 / Accepted: 23 April 2010 / Published: 4 May 2010

Download PDF Full-Text [172 KB, uploaded 4 May 2010 14:49 CEST]

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

Article Statistics

Click here to load and display the download statistics.

Cite This Article

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