Synthesis of Novel Thiophene-Fused 1,1’-Biazulene Derivative by the Reaction of Azuleno[1,2-b]thiophene with N-Iodosuccinimide

Shoji, Taku; Shimomura, Erika; Inoue, Yuta; Maruyama, Mitsuhisa; Yamamoto, Atsuyo; Fujimori, Kunihide; Ito, Shunji; Yasunami, Michio; Morita, Noboru

doi:10.3987/com-12-12638

Cited by 23 publications

(5 citation statements)

References 20 publications

(1 reference statement)

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“…Benzothiophenes are present in several drug candidates, and are widespread in materials chemistry . Among them, bibenzothiophenes are also an important class of compounds in functional materials,,,– and ligands ,. However, conventional methods for the synthesis of axially chiral bibenzothiophenes have been restricted to the optical resolution of racemates and diastereselective Stille coupling reactions using chiral auxiliaries –.…”

Section: Methodsmentioning

confidence: 99%

Asymmetric Cyclizative Dimerization of (ortho‐Alkynyl Phenyl) (Methoxymethyl) Sulfides with Palladium(II) Bisoxazoline Catalyst

Peng

Kusakabe

Kikkawa

et al. 2018

Chemistry A European J

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The first example of an asymmetric cyclization–dimerization of (ortho‐alkynyl phenyl) (methoxymethyl) sulfides with a palladium(II) bisoxazoline (box) catalyst has been developed. The box ligand enhances the alkynophilicity of benzothienyl palladium(II) intermediate A and thus promotes coordination of the second alkyne substrate, leading to the dimerization. The characteristic properties of the box ligand were supported by density functional theory (DFT) calculations of the intermediate. Axially chiral bibenzothiophenes were obtained in good yields with good enantioselectivities.

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Section: Methodsmentioning

confidence: 99%

Asymmetric Cyclizative Dimerization of (ortho‐Alkynyl Phenyl) (Methoxymethyl) Sulfides with Palladium(II) Bisoxazoline Catalyst

Peng

Kusakabe

Kikkawa

et al. 2018

Chemistry A European J

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“…Azulene derivatives usually react with NIS to give the corresponding 1-iodoazulene derivatives [ 71 ]. However, in the reaction of 112a with NIS, 1,1’-biazulene derivative 163 is formed in 74% yield instead of the expected iodoazulene derivative ( Scheme 39 ) [ 72 ]. A similar reaction with NBS and NCS forms neither the corresponding 1-haloazulenes or the 1,1’-biazulene derivative 163 , but only the decomposition is observed.…”

Section: Reactivity and Properties Of Azulene Derivatives Prepared From 2 H -Cyclohepta[ B ]Furan-2mentioning

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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“…Thiophene-fused azulenes sometimes exhibit a different reactivity from that of usual azulene derivatives. Thiophene-fused 1,1′-biazulene derivative 78 is obtained by the reaction of azuleno[1,2- b ]thiophene ( 77 ) with NIS, instead of the presumed iodoazulene derivative ( Scheme 25 ) [ 42 ]. NIS is commonly known as an iodination reagent, but it may act as an oxidant in this case.…”

Section: Synthesis and Reactivity Of Azulene Derivatives With 4- mentioning

confidence: 99%

Development of Heterocycle-Substituted and Fused Azulenes in the Last Decade (2010–2020)

Shoji

Okujima

Ito

2020

IJMS

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Azulene derivatives with heterocyclic moieties in the molecule have been synthesized for applications in materials science by taking advantage of their unique properties. These derivatives have been prepared by various methods, involving electrophilic substitution, condensation, cyclization, and transition metal-catalyzed cross-coupling reactions. Herein, we present the development of the synthetic methods, reactivities, and physical properties for the heterocycle-substituted and heterocycle-fused azulenes reported in the last decade.

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Synthesis of Novel Thiophene-Fused 1,1’-Biazulene Derivative by the Reaction of Azuleno[1,2-b]thiophene with N-Iodosuccinimide

Cited by 23 publications

References 20 publications

Asymmetric Cyclizative Dimerization of (ortho‐Alkynyl Phenyl) (Methoxymethyl) Sulfides with Palladium(II) Bisoxazoline Catalyst

Asymmetric Cyclizative Dimerization of (ortho‐Alkynyl Phenyl) (Methoxymethyl) Sulfides with Palladium(II) Bisoxazoline Catalyst

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

Development of Heterocycle-Substituted and Fused Azulenes in the Last Decade (2010–2020)

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