Synthesis of Methyl Azulen[1,2-<i>b</i>]azulene-2-carboxyl ate and Dimethyl Azulen[1,2-<i>b</i>]azulene-2,4-dicarboxylate

Kuroda, Shigeyasu; Hirooka, Syuzi; Iwaki, Hiroyuki; Ikeda, M.; Nakao, Takeshi; Ogisu, M.; Yasunami, Michio; Takase, Kahei

doi:10.1246/cl.1986.2039

Cited by 17 publications

(2 citation statements)

References 8 publications

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“…Reaction conditions: 1. toluene reflux; SiO 2 95 The "enamine" 12.1, rich in electrons at the double bond, reacts with 7.1, affording azulene fused to the five-membered ring, 12.2, as shown in Scheme 12 [23]. The hydrolysis and reaction with morpholine (in the presence of TiCl 4 ) give the intermediate I, which was treated in situ with methyl propiolate to the adduct 12.3.…”

Section: Mphmentioning

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: Mphmentioning

confidence: 99%

Syntheses of Azulene Embedded Polycyclic Compounds

Razus

2024

Symmetry

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“…Synthesis of azuleno[1,2- b ]azulene derivatives starting from 17 was established by Kuroda and Yasunami et al in 1986 ( Scheme 23 ) [ 48 ]. The reaction of 17 with the enamine in toluene at the reflux temperature yields 73 in 35% yield.…”

Section: Synthesis Of Azulenes By the Reaction Of 2 H -Cyclohepta[ B ]Furan-2-ones With Enaminesmentioning

confidence: 99%

Synthesis of Azulene Derivatives from 2H-Cyclohepta[b]furan-2-ones as Starting Materials: Their Reactivity and Properties

Shoji

Ito

Yasunami

2021

IJMS

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A variety of synthetic methods have been developed for azulene derivatives due to their potential applications in pharmaceuticals and organic materials. Particularly, 2H-cyclohepta[b]furan-2-one and its derivatives have been frequently used as promising precursors for the synthesis of azulenes. In this review, we describe the development of the synthesis of azulenes by the reaction of 2H-cyclohepta[b]furan-2-ones with olefins, active methylenes, enamines, and silyl enol ethers as well as their reactivity and properties.

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IntermolecularCyclization Reactions to form Carbocycles

Beusker

Scheeren

2009

Patai's Chemistry of Functional Groups

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General Introduction [2 + 2] Cycloaddition Reactions D iels– A lder Reactions [6 + 4] Cycloaddition Reactions [8 + 2] Cycloaddition Reactions [2 + 2 + 2] Cycloaddition Reactions

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Synthesis of Methyl Azulen[1,2-b]azulene-2-carboxyl ate and Dimethyl Azulen[1,2-b]azulene-2,4-dicarboxylate

Abstract: The titled compounds were synthesized. The complete assignment of 1H-NMR spectrum of methyl azulen[1,2-b]azulene-2-carboxylate and the rearrangement of ester group on seven membered ring in the dehydrogenation reaction are described.

Cited by 17 publications

References 8 publications

Syntheses of Azulene Embedded Polycyclic Compounds

Syntheses of Azulene Embedded Polycyclic Compounds

Synthesis of Azulene Derivatives from 2H-Cyclohepta[b]furan-2-ones as Starting Materials: Their Reactivity and Properties

IntermolecularCyclization Reactions to form Carbocycles

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