Reactions of amidrazones with 1,4-quinones

Abstract

Syntheses of various benzo-and naphtho-1,2,4-triazin-6(4H)-ones are formed in one step via the reactions of amidrazones with benzo-and naphtho-1,4-quinones. In contrast, the reactions of amidrazones with 2,3,5,6-tetrachloro-1,4-benzoquinone or 2,3-dichloro-1,4-naphthoquinone produced the same indazoles, no matter what substituents were present on the nitrogen of the amidrazone.

Regioselective synthesis of 5-aminopyrazoles from reactions of amidrazones with activated nitriles: NMR investigation and X-ray structural analysis

“…Amidrazones are also found to be effective herbicides (Dean et al, 2008). We have reported that amidrazones react with 1,4-benzoquinone or 1,4-naphthoquinone to give annulated 1,2,4-triazines , but with 2,3,5,6-tetrachloro-1,4-benzoquinone and 2,3-dichloro-1,4-naphthoquinone to afford indazole derivatives (Aly et al, 2007). We also reported that reaction of amidrazones with 1,4-dioxo-1,4dihydronaphthalene-2,3-dicarbonitrile gave a variety of 1,2,4-triazepines (Aly et al, 2008).…”

An Efficient Synthesis of Highly Substituted Spiro[Fluorene-9,3′-[1,2,4]Triazoles from the Reaction of N3-Substituted Amidrazones with (2,4,7-Trinitro-9H-Fluoren-9-Ylidene)Propanedinitrile

“…Amidrazones are an important class of amidines, as they can be used as synthons for 1,2,4-triazoles, 1 pyridines, 2 1,2,4-triazines, 2,3 1,2,4-triazepines 4 and other heterocyclic systems. 5,6 Amidrazones with three nitrogen nucleophiles are essential components of molecules exhibiting high biological activities, e.g.…”

“…9 Interestingly, a very convenient procedure to synthesise 1,2,4-triazines in one step has been developed by rapid reaction of amidrazones with benzo-and naphtho-1,4-quinones. 10 Recently, we reacted amidrazones with 2-cyano-3,3bis(methylthio)acrylate to obtain mercaptopyrazole derivatives. 11 Furthermore, when amidrazones were reacted with diaminomalononitrile, iminopyrazoles were formed.…”

Reaction of Amidrazones with 2,3-Diphenylcyclopropenone: Synthesis of 3-(aryl)-2,5,6-Triphenylpyrimidin-4(3H)-ones

“…In contrast, the reactions of amidrazones with 2,3,5,6-tetrachloro-1,4-benzoquinone or 2,3-dichloro-1,4-naphthoquinone gave indazoles. 17 Recently, we reacted amidrazones with 2-cyano-3,3-bis(methylthio)acrylate to give mercapto pyrazole derivatives. 18 We have also investigated the chemistry of 1 in heterocyclic synthesis, such as pyridazinethiones, 1,2,4-triazolo [4,3-b] pyridazinethiones 19 and [2.2]paracyclophane-based pyrroles.…”