Aromatic heterocycle synthesis pyridazines

The most useful procedure utilises a 1,4-keto-ester giving a dihydro-pyridazinone, which can be easily dehydrogenated to the fully aromatic heterocycle, often by C-bromination then dehydrobromination alternatively, simple air oxidation can often suffice. 6-Aryl-pyridazin-3-ones have been produced by this route in a number of ways using an a-amino nitrile as a masked ketone in the four-carbon component, or by reaction of an acetophenone with glyoxylic acid and then hydrazine. Friedel-Crafts acylation using succinic anhydride is an alternative route to 1,4-keto-acids, reaction with hydrazine giving 6-aryl-pyridazinones. Alkylation of an enamine with a phenacyl bromide prodnces 1-aryl-l,4-diketones, allowing synthesis of 3-aryl-pyridazines. ... 

Jacoby (187) and the Hamilton group (188-191) suggested that bis- or tris-aromatic residues could serve as scaffolds for helical mimetics. Che et al. have examined a variety of aromatic-based scaffolds as potential helix mimetics (192). Rebek and coworkers have suggested a central pyridazine ring (193) as well as a heterocyclic piperazine-based scaffold (194). Ahn and Han developed a facile synthesis of benzamides as potential helix mimetics (195). 

Using electrophilic and nucleophilic aromatic substitution in five- and six-membered heterocycles. Chemo- and regioselectivity The synthesis of pyridazines... 

This family of foidamers consists of two, three, or five alternating aromatic heterocydes (pyridazine, pyrimidine, or pyrazine) and methyl-substituted aromatic carbocycles (tolyl, o-xylyl, or m-xylyl) cormected via urea groups (8 Figure 9.3) [14]. In a typical synthesis, heterocyclic diamine compounds were treated with aryl diisocyanate compounds to install a urea linkage between aromatic heterocyde and aromatic carbocyde (Umax = 5). 

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