Synthesis, characterization and applications of densely functionalized pyridazines and fulvene-type compounds containing azulene moiety

Devendar, Badugu; Wu, Chi‐Phi; Chen, Chi-Yuan; Chen, Hung-Chang; Chang, C.‐C.; Ku, Chien-Kuo; Tsai, C. S.; Ku, Chieh-Yuan

doi:10.1016/j.tet.2013.04.034

Cited by 10 publications

(3 citation statements)

References 32 publications

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“…Both reactions occurred with excellent yield. Among the azulenic tricyclic compounds grafted with a heterocyclic system, the ethyl 1H-azuleno [8,1-cd]-pyridazine-5-carboxylates, 46.3 contain two nitrogen atoms in the condensed ring [70]. The compound was formed after the reaction of a highly efficient substrate for electrophilic substitutions, ethyl 4-ethoxy-3-formylazulene-1-carboxylate 46.1, with hydrazine (Scheme 46).…”

Section: Scheme 42 Synthesis Of Azulenophthalimides and Bis(azulenoph...mentioning

confidence: 99%

Syntheses of Azulene Embedded Polycyclic Compounds

Razus

2024

Symmetry

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This review focuses on obtaining embedded azulene polycyclic molecules treated according to their particular structure. The division of material into the azulene unit grafted only on one or two bonds and poly-fused azulene compounds was suggested with the intention of facilitating the presentation and assimilation of information. The similarity of some structural features in the compounds included in different analyzed classes results in the presence of the same synthesis protocol in several places. Obtaining benz[a]azulenes, azulene-fused acenes, and helicenes or azulene-embedded nanographene, along with other compounds, is presented.

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Section: Scheme 42 Synthesis Of Azulenophthalimides and Bis(azulenoph...mentioning

confidence: 99%

Syntheses of Azulene Embedded Polycyclic Compounds

Razus

2024

Symmetry

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“…The ethyl 1H-azuleno [8,1-cd]-pyridazine-5-carboxylate, 54.2, resulted in the reaction of ethyl 4-ethoxy-3-formylazulene-1-carboxylate, 54.1, with hydrazine (Scheme 54). Presumably, the reaction occurred via a substitution reaction and subsequent intramolecular condensation [80]. By replacing hydrazine with phenylhydrazine, the fulvenic compound 54.3 was formed as a product.…”

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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“…Fulvene derivatives, which exhibit intriguing chemical properties, are significant organic compounds usually being treated as synthetic building blocks . They are not only widely used in the synthesis of various kinds of functional materials but also recognized as privileged scaffolds, which can be found in many natural products and pharmaceuticals .…”

Section: Introductionmentioning

confidence: 99%

Ethyl 6-Hydroxyfulvene-1-Carboxylate: A Reagent Discriminating Primary Amines from Secondary Amines

Yang

Zhu

et al. 2018

J. Org. Chem.

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A highly chemo-selective reaction was observed when ethyl 6-hydroxyfulvene-1-carboxylate 1 was treated with different nucleophiles such as primary amines, secondary amines, alcohols, and thiols. Among them, only primary amines are reactive toward 1 to afford the condensation products 3, which exhibit good stability under both weakly acidic and basic conditions. The condensation process proved to be reversible between different primary amines. On the basis of this observation, the chemical selectivity of typical primary aromatic amines was evaluated quantitatively by determining equilibrium constants of the condensation reactions with aniline as a reference. Moreover, the primary amines of 3 can be readily released upon treatment with aqueous ammonia, making 6-hydroxyfulvene-1-carboxylate 1 a promising protecting reagent for primary amines.

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Synthesis, characterization and applications of densely functionalized pyridazines and fulvene-type compounds containing azulene moiety

Cited by 10 publications

References 32 publications

Syntheses of Azulene Embedded Polycyclic Compounds

Syntheses of Azulene Embedded Polycyclic Compounds

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

Ethyl 6-Hydroxyfulvene-1-Carboxylate: A Reagent Discriminating Primary Amines from Secondary Amines

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