6,12-Bis(hexyloxy)-5H,11H-indolo[3,2-b]carbazole

Wrobel, Norma; Witulski, B.; Schollmeyer, Dieter; Detert, Heiner

doi:10.1107/s1600536812050611

Cited by 4 publications

(4 citation statements)

References 15 publications

(10 reference statements)

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“…The Cadogan cyclization has previously been recognized on several occasions as a useful tool for indolo[3,2- b ]carbazole synthesis ,, and has more recently been employed for the synthesis of compound 272 bearing alkyl ether substituents from the precursor 273 (Scheme ). The structure of the product 272 was corroborated by X-ray crystallography . Similar strategy was used by the same group for preparation of the closely related 5,11-dihydro-6,12-dimethoxy-5,11-dimethylindolo[3,2- b ]carbazole, which was also subjected to a single-crystal X-ray study .…”

Section: Indolo[32-b]carbazolesmentioning

confidence: 78%

“…The structure of the product 272 was corroborated by X-ray crystallography. 279 Similar strategy was used by the same group for preparation of the closely related 5,11-dihydro-6,12-dimethoxy-5,11dimethylindolo[3,2-b]carbazole, which was also subjected to a single-crystal X-ray study. 280 In this context, it is also worth mentioning that a single example of an indolo[3,2-b]carbazole has been reported as a minor product in low yield from a conceptually related palladium-catalyzed reductive cyclization of a nitroaromatic precursor in the presence of hydrogen.…”

Section: Synthesis and Reactionsmentioning

confidence: 99%

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Chemistry and Properties of Indolocarbazoles

et al. 2018

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The indolocarbazoles are an important class of nitrogen heterocycles which has evolved significantly in recent years, with numerous studies focusing on their diverse biological effects, or targeting new materials with potential applications in organic electronics. This review aims at providing a broad survey of the chemistry and properties of indolocarbazoles from an interdisciplinary point of view, with particular emphasis on practical synthetic aspects, as well as certain topics which have not been previously accounted for in detail, such as the occurrence, formation, biological activities, and metabolism of indolo[3,2- b]carbazoles. The literature of the past decade forms the basis of the text, which is further supplemented with older key references.

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Section: Indolo[32-b]carbazolesmentioning

confidence: 78%

Section: Synthesis and Reactionsmentioning

confidence: 99%

Chemistry and Properties of Indolocarbazoles

et al. 2018

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“…For other approaches to indolocarbazoles, see: Knö lker & Reddy (2002); Katritzky et al (1995). For the structure of N-unsubstituted indolocarbazole, see: Wrobel et al (2013). For electronic properties of indolocarbazoles, see: Hu et al (1999); Wakim et al (2004); Nemkovich et al (2009).…”

Section: Related Literaturementioning

confidence: 99%

5,11-Dimethyl-6,12-dimethoxyindolo[3,2-b]carbazole

et al. 2013

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Key indicators: single-crystal X-ray study; T = 193 K; mean (C-C) = 0.003 Å; R factor = 0.049; wR factor = 0.152; data-to-parameter ratio = 13.4.The title compound, C 22 H 20 N 2 O 2 , was prepared in a twofold Cadogan cyclization followed by double N-methylation. The crystal structure is characterized by a zigzag arrangement of centrosymmetric molecules. The indolocarbazole framework is essentially planar [maximum deviation = 0.028 (2) Å ] and the methoxy groups are orthogonal to this plane [C-C-O-C torsion angle = À88.2 (2) ]. The lengths of the C-N bonds are nearly identical and all C-C bonds of the pyrrole subunit are significantly longer than the C-C bonds in the benzene rings.

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“…The building block ( B.B. ) was synthesized based on the reference (SI), and its cyclization was catalyzed by FeCl 3 ·6H 2 O to give cub[4]indolocarbazole (Scheme ). All the compounds had been fully characterized by 1 H NMR, 13 C NMR, and HRMS spectra (Figures S1–S24).…”

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confidence: 99%

N-Embedded Cubarene: A Quadrangular Member of the Macrocycle Family

Zhang

Sun

et al. 2023

Org. Lett.

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Despite the large number of synthetic macrocycles, the cubarenes, the quadrangular-shaped macrocyclic arenes, remain less investigated, possibly due either to synthetic challenges or to the lack of suitable building blocks. In this paper, a N-embedded cubarene (cub[4]indolocarbazole) is facilely synthesized by FeCl 3 •6H 2 O-catalyzed cyclization in dichloromethane. The endo cavity of cub[4]indolocarbazole can bury quaternary ammonium salts in an intramolecular manner, whereas the intermolecular interaction between its exo walls with Cu 2+ generates two-dimensional supramolecular tessellation.

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6,12-Bis(hexyloxy)-5H,11H-indolo[3,2-b]carbazole

Cited by 4 publications

References 15 publications

Chemistry and Properties of Indolocarbazoles

Chemistry and Properties of Indolocarbazoles

5,11-Dimethyl-6,12-dimethoxyindolo[3,2-b]carbazole

N-Embedded Cubarene: A Quadrangular Member of the Macrocycle Family

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