Benz[a]azulenequinones: Reaction of Benz[a]azulenes with Pyridinium Hydrobromide Perbromide

Shoji, Taku; Yamazaki, Akari; Sakata, Naoko; Sekiguchi, Ryuta; Ito, Shunji; Yasunami, Michio

doi:10.3390/m1467

Cited by 2 publications

(1 citation statement)

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“…In these reactions, the participation of the azulene seven-atom ring in the formation of benz[a]azulenequinones, 53.2, was highlighted. Considering the toxicity of bromine and the poor results when MnO2 was used as oxidant, as well as the complexity of the reaction mixture obtained in these reactions, Shoji et al [79] used pyridinium hydrobromide perbromide as an oxidant with acceptable results, as described in Scheme 53. The azulenic tricyclic compounds can also contain a heterocyclic system.…”

Section: Polycyclic Compounds That Include the Azulenic Systemmentioning

confidence: 99%

Azulene, Reactivity, and Scientific Interest Inversely Proportional to Ring Size; Part 2: The Seven-Membered Ring

Razus

2023

Symmetry

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The second part of the article Azulene, Reactivity, and Scientific Interest Inversely Proportional to Ring Size deals with the chemical behavior of the seven-atom azulenic ring. As the title states, the ability of this system to react is lesser compared to that of the five-atom ring; despite this, a large number of syntheses contain it as a participant in the molecules of starting compounds. This review is focused on certain more frequent syntheses such as nucleophilic substitution of the seven-atom ring or its substituents, vicarious nucleophilic substitutions, substitutions of azulene metallic compounds, or reactions catalyzed by complexes of certain transition metals. The syntheses of tricyclic compounds, porphyrinogenic systems, or azulenocyanines containing an azulenyl moiety are also presented. The adopted presentation is mainly based on reaction schemes that include the reaction conditions, as well as the yields of the products formed.

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Section: Polycyclic Compounds That Include the Azulenic Systemmentioning

confidence: 99%