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Samsoniya, Sh. A.; Trapaidze, M. V.; Machaidze, N. N.; Durr, G. J.

doi:10.1023/a:1016019002989

Cited by 6 publications

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“…The number of synthetic routes towards indolo[7,6‐ g ]indoles has not attracted as much attention as the above‐mentioned isomers. Since the work of Samsoniya, [24a,b] only a few methods have been reported in this domain. Of note is the Rh(III)‐catalysed regioselective functionalization of C−H bonds of naphthyl carbamates 87 for oxidative annulation with alkynes 88 [41] .…”

Section: Methods For the Synthesis Of Indolo[76‐g]indolesmentioning

confidence: 99%

Recent Advances towards the Synthesis and Material Applications of Indoloindoles

Paul

John

2022

Chemistry An Asian Journal

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An important class of N-heteroacenes is indoloindoles which are air-stable, electron-rich and possess many tuneable properties. Initially, indoloindoles were explored for potential biological applications but current interest is based on their performance as photovoltaic materials. With growing applications of indoloindoles across multiple facets as organic functional materials, the need for efficient methods to synthesize and functionalize indoloindoles has taken a centre stage. Over the years, synthetic routes leading to indoloindoles have evolved from multistep protocols to one-pot multicomponent synthesis. Present literature boasts of a variety of reports that employ metals such as Cu, Ru, Rh, Pd, or Au to mediate the reaction towards indoloindoles. As alternatives to such metal-mediated methods, researchers have also developed metal-free and catalyst-free conditions. Indoloindoles, which are fundamentally fused-indoles, are often synthesized by transforming indole derivatives but methods that employ anilines or arynes as the starting substrates are equally abundant. The present review highlights the rich diversity and versatility of recent literature for the synthesis of indolo[3,2-b]indoles, indolo[2,3-b]indoles, indolo[7,6-g]indoles, and indolo [5,4-e]indoles. This review discusses protocols that were explicitly designed to obtain the above-mentioned indoloindoles and also explores several other methods that can be adapted to access said heteroacenes. Available mechanistic details pertaining to novel transformations have been detailed for the readers. Various applications where indoloindoles function as organic lightemitting diodes, organic field-effect transistors, solar cells, etc. have also been delved into before concluding with an outlook on future research.

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Section: Methods For the Synthesis Of Indolo[76‐g]indolesmentioning

confidence: 99%

Recent Advances towards the Synthesis and Material Applications of Indoloindoles

Paul

John

2022

Chemistry An Asian Journal

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“…8 The structure of the bisindolenine 10 was evident from its molecular formula, the twelvehydrogen singlet for the geminal methyl groups, at δ 1.33 ppm, and a singlet signal for the imine methyl groups resonating at δ 2.30 ppm.…”

Section: Methodsmentioning

confidence: 99%

Synthesis of 2,2′-bis(1-(2-aryl)-1H-pyrazol-4-yl)-3,3,3′,3′-tetramethyl-3H,3′H-5,5′-biindoles and 2,7-bis(1-(3-aryl)-1H-pyrazol-4-yl)-1,1,6,6-tetramethyl-1,6-dihydroindolo[7,6-g]indoles

Baradarani¹,

Joule²,

Rashidi³

2011

Arkivoc

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Synthesis of 2,2′-bis(1-(2-aryl)-1H-pyrazol-4-yl)-3,3,3′,3′-tetramethyl-3H,3′H-5,5′-biindoles and 2,7-bis(1-(3-aryl)-1H-pyrazol-4-yl)--(naphthalene-1,5-diyl)bis (hydrazinium) chloride were converted via Fischer syntheses with 3-methylbutan-2-one into bisindolenines, 2,2′,3,3,3′,3′-hexamethyl-3H,3′H-5,5′-biindole 10 and 2, 3,3,7,8,8-hexamethyl-3H,8H-indolo[7,6-g]indole 14, respectively. Exposure of the bisindolenines to the Vilsmeier reagent produced tetraformyl compounds 11 and 15, which reacted with hydrazine and arylhydrazines to give the corresponding pyrazoles 12 and 16 in excellent yields.Keywords: Arylhydrazines, bisindolenine, Fischer reaction, hydrazine, pyrazole, Vilsmeier reagent IntroductionWe recently described the reaction of 2,3,3-trimethylindolenines (3H-indoles) 1 with the Vilsmeier reagent formed from dimethylformamide and phosphorus oxychloride to produce aminomethylene malondialdehydes 2 (Scheme 1).1,2 Additionally we showed that the pyridoindolenines 2,3,3-trimethyl-3H-pyrrolo[2,3-f]quinoline and 2,3,3-trimethyl-3H-pyrrolo[3,2-h]quinoline 4 behave similarly (Scheme 2). The malondialdehydes 2,5 reacted with hydrazine or arylhydrazines to produce substituted pyrazoles 3,6. 1,3,4 We have now been able to show that the principles embodied in these transformations can be incorporated into bisindolenine systems, and thus have prepared several more complex pyrazoles. Scheme 2For the mechanism of formation of the aminomethylene malondialdehydes, we suggested that a small equilibrium concentration of an enamine tautomer 7 is successively C-substituted and thus, before hydrolysis during work-up, species 8 is present (Scheme 3). We propose that a comparable mechanism operates in the work described herein. Scheme 3 Results and DiscussionDiazotisation of benzidine and naphthalene-1,5-diamine, then reduction of the diazonium salts with tin(II) chloride, produced the corresponding bis hydrazinium chlorides 9 and 13. 5 Reaction of 2,2′-(biphenyl-4,4′-diyl)bis(hydrazinium)chloride 9 with isopropyl methyl ketone in a Fischer reaction 6 produced the bisindolenine 2,2′,3,3,3′,3′-hexamethyl-3H,3′H-5,5′-biindole 10 in good yield (Scheme 4).

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“…The subject of the present study were our synthesized spirocyclic compounds bis[2`,3`-bis(methoxycarbonyl)-5`,6`,6`-trimethylspirofluoren-9,4`-(1`-aza-2`-cyclopentene)][1`,5`-a]indolino [4,5-e]indoline (I) and bis[2`,3`-bis(methoxycarbonyl)-5`,6`,6`-trimethylspirofluoren-9,4`(1`-aza-2`-cyclopentene)][1`,5`-a]indolino-[7,6-g]indoline (II), that exhibit protochromic properties [1,2].On exposure to light compound I passes into a colored unstable betaine form III. Its electronic ÄÄÄÄÄÄÄÄÄÄÄÄ spectra acquire absorption bands at lmax 325 and 550 nm (Fig.…”

mentioning

confidence: 99%

“…2). Because of the fast conversion of compound II, absorption maxima of the corresponding betaine could not be detected [2]. We could detect the betaine formation and measure its t 0.5 of 0.043 s by measuring a narrower spectral region (shorter time measurements) (Fig.…”

mentioning

confidence: 99%

Structure-Property Relationship in Bispyrrolizidine Photochromic Compounds Derived from Indolo[4,5-e]- and -[7,6-g]indoles

et al. 2005

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The spirocyclic compounds bis[2`,3`-bis(methoxycarbonyl)-5`,6`,6`-trimethylspirofluoren-9,4`-(1`-aza-2`-cyclopentene)][1`,5`-a]indolino[4,5-e]indoline and bis[2`,3`-bis(methoxycarbonyl)-5`,6`,6`-trimethylspirofluoren-9,4`-(1`-aza-2`-cyclopentene)][1`,5`-a]indolino[7,6-g]indoline exhibit photochromic properties with various half-lifes. The AM1 method was used to correlate the structural and electronic properties, on the one hand, and photochromic properties, on the other, and to explain reasons for the difference in the photochromism of the two compounds.

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Cited by 6 publications

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Recent Advances towards the Synthesis and Material Applications of Indoloindoles

Recent Advances towards the Synthesis and Material Applications of Indoloindoles

Synthesis of 2,2′-bis(1-(2-aryl)-1H-pyrazol-4-yl)-3,3,3′,3′-tetramethyl-3H,3′H-5,5′-biindoles and 2,7-bis(1-(3-aryl)-1H-pyrazol-4-yl)-1,1,6,6-tetramethyl-1,6-dihydroindolo[7,6-g]indoles

Structure-Property Relationship in Bispyrrolizidine Photochromic Compounds Derived from Indolo[4,5-e]- and -[7,6-g]indoles

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