157368-88-2

Upstream product

• 64-17-5 ethanol 
• 460-19-5 ethanedinitrile 
• 106-49-0 p-toluidine 
• 7472-70-0 N,N'-bis(4-methylphenyl)ethanediimidoyl dichloride 
• 78-90-0 1,2-diaminopropan 
• 2074-87-5 carbon nitride 

Downstream Products

• 2580-79-2 diaminoglyoxime 
• 3299-61-4 N,N'-Di-p-tolyloxalamide 
• 42868-90-6 p-tolyl-oxalamide 
• 200510-95-8 [5-(4-Methylphenylamino)-4-(4-methylphenylimino)-4H-imidazol-2-yl]-benzene 
• 936830-35-2 6-imino-5-(4-tolyl)-7-(4-tolylamino)-5,6-dihydropyrazino[2,3-b]pyrazine-2,3-dicarbonitrile 

Relevant academic research and scientific papers

Bis-amidines as useful building blocks for heterofulvenes and -fulvalenes

An easily feasible synthesis for bis-amidines of type 3 was developed via an aminolysis reaction of imidoyl chlorides 1 with gaseous ammonia. Depending on the nature of the electrophilic cyclization reagent, these amidines show a different reactivity. On treatment with orthoesters, the fused imidazoles 5 were obtained which involved the participation of two different kinds of nitrogen atoms in the cyclization. In contrast to this, carboxylic acid chlorides are able to react selectively at the NH2-groups under formation of the fulvenoid 4H-imidazoles 6. The same regioselectivity was observed for chlorodimethylimmonium chloride thus leading, via the dimerization of cyclic orthoamides, to the 1,4,5,8-tetraazafulvalenes 8.

On the Aminolysis of Bis-Imidoylchlorides of Oxalic Acid. II. Reaction with Aliphatic Diamines and Aminoalcohols

The aminolysis of bis-imidoylchloride 1 derived from oxalic acid with several diamines and aminoalcohols was investigated.At room temperature diamines 2 as well as aminoalcohols 7 give mainly the cyclic amidines 3 and mixed amidine-imidates 8 in moderately up to good yields.While cis-1,2-diaminocyclohexane yields at room temperature the bicyclic amidine 3a, the trans isomer reacts to 3b only when heated for several hours.Depending on the conditions, the racemic 1,2-diaminopropane 2h gives derivatives of pyrazine 3h or the open-chain amidine 5 resulting from an oxidative aromatization and subsequent hydrolysis.Histamine 2i and 1,8-diamino-3,6-dioxaoctane 2p react selectively with 1 to seven- respectively twelve-membered heterocycles 3i and 3p.The mixed aliphatic and aromatic diamines 2n, o show an anomalous behaviour leading to 2,2'-bis-chinazolines 3n, o.In comparison with acyclic oxalic amidines the new cyclic derivatives show less molecular dynemic in their nmr spectra.In some cases, a s-trans-arrangement of the amidine substructure was observed.