The chemistry of carbazoles. VII. Syntheses of methylcarbazoles

Kuroki, Masatane; Tsunashima, Yutaka

doi:10.1002/jhet.5570180414

Cited by 57 publications

(19 citation statements)

References 43 publications

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“…In the case of methoxy carbazoles, particularly for the entry nos. 16,17,18,19,23, and 24, often isolation and purification was carried out through vacuum (0.5 mm of Hg) sublimation.…”

Section: Methodsmentioning

confidence: 99%

A Tandem Reduction–Oxidation Protocol for the Conversion of 1‐Keto‐1,2,3,4‐tetrahydrocarbazoles to Carbazoles via Tosylhydrazones through Microwave Assistance: Efficient Synthesis of Glycozoline, Clausenalene, Glycozolicine, and Deoxycarbazomycin B and the Total Synthesis of Murrayafoline A

Chakraborty¹,

Chattopadhyay

Saha³

2013

Journal of Heterocyclic Chem

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A novel and efficient methodology for the synthesis of carbazoles from 1-keto-1,2,3,4-tetrahydrocarbazoles via the corresponding tosylsulfonhydrazones by a one-pot tandem reduction-oxidation protocol using a combination of NaBH 4 and Pd-C on MgSO 4 Á7H 2 O, a solid support, under microwave is developed. The reaction is successfully extended toward the synthesis of several naturally occurring carbazole alkaloids, namely 3-methylcarbazole, glycozoline, clausenalene, glycozolicine, murrayafoline A, and deoxycarbazomycin B, a carbazole derivative that is known to have a promising antimicrobial activity.

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“…In the case of methoxy carbazoles, particularly for the entry nos. 16,17,18,19,23, and 24, often isolation and purification was carried out through vacuum (0.5 mm of Hg) sublimation.…”

Section: Methodsmentioning

confidence: 99%

A Tandem Reduction–Oxidation Protocol for the Conversion of 1‐Keto‐1,2,3,4‐tetrahydrocarbazoles to Carbazoles via Tosylhydrazones through Microwave Assistance: Efficient Synthesis of Glycozoline, Clausenalene, Glycozolicine, and Deoxycarbazomycin B and the Total Synthesis of Murrayafoline A

Chakraborty¹,

Chattopadhyay

Saha³

2013

Journal of Heterocyclic Chem

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“…The 2-nitrobiphenyl can then be easily transformed into a carbazole unit using a Cadogan ring closure reaction. [126][127][128][129][130] Scheme 9 shows the synthesis of N-(2 0 -ethylhexyl)-2,7-dichlorocarbazole using this strategy. [131] This strategy afforded, in three steps, reactive 2,7-functionalised carbazole monomers that can be used in the Yamamoto cross-coupling reaction to synthesise various polymers.…”

Section: Synthesis and Properties Of 27-carbazole-based Polymersmentioning

confidence: 99%

Polycarbazoles: 25 Years of Progress

Morin

Leclerc

Adès

et al. 2005

Macromol. Rapid Commun.

612

365

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Summary: Carbazole‐based oligomeric and polymeric materials have been studied for almost 25 years for their unique electrical, electrochemical and optical properties. Interestingly, carbazole units can be linked in two different ways leading to either poly(3,6‐carbazole) or poly(2,7‐carbazole) derivatives. While the former class seems to be very interesting for electrochemical and phosphorescence applications, the latter shows very promising optical properties in the visible range for light emitting diodes (LED). The major intrinsic difference between these two classes is the effective conjugation length: poly(2,7‐carbazole) materials having the longer one, due to their poly(p‐phenylene)‐like structure. Using different synthetic strategies and substitution patterns, the physico‐chemical properties of both classes can be fine‐tuned, leading to high performance materials for a large number electronic applications.Chemical structures for poly(3,6‐carbazole) and poly(2,7‐carbazole) and the materials used as the starting points for their respective syntheses.magnified imageChemical structures for poly(3,6‐carbazole) and poly(2,7‐carbazole) and the materials used as the starting points for their respective syntheses.

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“…The second building block, 3‐methylcarbazole, was made by coupling 4‐methylhydrazine hydrochloride and cyclohexanone to the corresponding hydrazone, followed by a ring closing Fischer‐type indol reaction. According to the literature,17 the resulting tetrahydrocarbazole intermediate was used without further purification and dehydrogenated with palladium on charcoal to yield 80% of 3‐methylcarbazole as white crystals. The 1,3‐dicarbazolylbenzene monomer 4 was generated in a palladium‐catalyzed Buchwald‐Hartwig‐type amination of both monomers (1,6‐dibromo‐5‐ tert ‐butylbenzene and 3‐methylcarbazole) with Pd 2 dba 3 as the catalyst, biphenyl‐2‐di‐ tert ‐butylphosphine (JohnPhos) as (co)ligand and NaO‐ t ‐Bu as base.…”

Section: Experimental Partmentioning

confidence: 99%

Form or function? Part 1. Subjective cosmetic and functional correlates of quality of life in women treated with breast-conserving surgical procedures and radiotherapy

Stanton

Krishnan

Collins

2001

Cancer

133

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When aqueously prepared CdTe nanocrystals (NCs) are coated with a SiO2 shell containing Cd ions and a sulfur source, they show a drastic increase in photoluminescence (PL) efficiency with a significant red shift and spectral narrowing after reflux. This is ascribed to the creation of a hybrid structure characterized by the formation of CdS‐like clusters in the vicinity of the NCs in the SiO2 shell. Since these clusters are close to the NCs, their effective size increases to reduce the quantum size effect. The dependences of the PL properties on the preparation conditions are systematically investigated. The PL efficiency increases from 28% to 80% in the best case with a red shift of 80 nm. The PL behaviors differ from those of normal CdTe NCs and include less temperature quenching and longer PL lifetime. The SiO2 coating enables bioconjugation with IgG without deterioration of PL efficiency, making hybrid NCs amenable for bioapplication.

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The chemistry of carbazoles. VII. Syntheses of methylcarbazoles

Abstract: Thirty‐six methylcarbazoles were prepared, and their synthetic methods were critically described.

Cited by 57 publications

References 43 publications

A Tandem Reduction–Oxidation Protocol for the Conversion of 1‐Keto‐1,2,3,4‐tetrahydrocarbazoles to Carbazoles via Tosylhydrazones through Microwave Assistance: Efficient Synthesis of Glycozoline, Clausenalene, Glycozolicine, and Deoxycarbazomycin B and the Total Synthesis of Murrayafoline A

A Tandem Reduction–Oxidation Protocol for the Conversion of 1‐Keto‐1,2,3,4‐tetrahydrocarbazoles to Carbazoles via Tosylhydrazones through Microwave Assistance: Efficient Synthesis of Glycozoline, Clausenalene, Glycozolicine, and Deoxycarbazomycin B and the Total Synthesis of Murrayafoline A

Polycarbazoles: 25 Years of Progress

Form or function? Part 1. Subjective cosmetic and functional correlates of quality of life in women treated with breast-conserving surgical procedures and radiotherapy

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