Online article for Non-subscribers

Pay per view

Heterocycles has a pay-per-view service for Non-subscribers.
You will be able to directly purchase the full text article through PayPal.
Your purchased Paper can be downloaded after the payment is completed.
An e-mail will be sent the URL to download the paper.
If you have any questions, please contact: purchase@heterocycles.com

Price: ¥ 4,400 (Yen only)
Period: This Article can be accessed for 7 days.

Report | Regular issue | Vol 23, No. 3, 1985, pp.683-690
Published online, 1st January, 1970
DOI: 10.3987/R-1985-03-0683
■ 4-Nitro- and 4-Cyanopyridazines

Antonius T. M. Marcelis and Henk C. van der Plas*

*Laboratory of Organic Chemistry, Agricultural University, De Dreijen 5, 6703 BC Wageningen, The Netherlands

Abstract

3-Acyl-1,2,4,5-tetrazines react with 1-nitro-2-dimethylaminoethene and 1-cyano-2-morpholinoethene by an inverse electron demand Diels-Alder reaction to give, after elimination of nitrogen and the secondary amine, the corresponding 3-aryl-5-nitro- and 3-aryl-5-cyanopyridazines. Besides these compounds, 1-benzylidene-2-dialkylaminomethylenehydrazines were isolated. They are also obtained from reaction of the 3-aryl-1,2,4,5-tetrazines with secondary aliphatic amines. Tetrazines with two electron-withdrawing groups like 3,6-bis(2-pyridyl)-1,2,4,5-tetrazine, 3,6-bis(4-pyridyl)-1,2,4,5-tetrazine and 3,6-bis(piperidinocarbonyl)-1,2,4,5-tetrazine also react with the nitro- or cyanoenamine to give the corresponding 3,6-disubstituted 4-nitro- or 4-cyanopyridazines.