A facile synthesis of phenazine and quinoxaline (new 1,4-benzo diazine) derivatives using magnesium sulfate heptahydrate as a catalyst

Karami, Bahador; Khodabakhshi, Saeed

doi:10.2298/jsc100801104k

Cited by 13 publications

(8 citation statements)

References 10 publications

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“…From a synthetic perspective, chemical reactions for synthesizing linear conjugated polymers, such as the Suzuki cross-coupling reaction, 28,29 Yamamoto reaction, 30,31 Sonogashira-Hagihara reaction, 32,33 oxidative coupling, 34,35 Schiff-base reaction, 10,36 cyclotrimerization, 37,38 phenazine ring fusion reaction 39,40 and Friedel-Crafts arylation, 41,42 are effective for the preparation of CMPs. The diversity of building blocks, coupled with the wide availability of different reaction types, make CMPs an invaluable platform for developing new organic porous materials.…”

Section: Introductionmentioning

confidence: 99%

Conjugated microporous polymers: design, synthesis and application

et al. 2013

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Conjugated microporous polymers (CMPs) are a class of organic porous polymers that combine π-conjugated skeletons with permanent nanopores, in sharp contrast to other porous materials that are not π-conjugated and with conventional conjugated polymers that are nonporous. As an emerging material platform, CMPs offer a high flexibility for the molecular design of conjugated skeletons and nanopores. Various chemical reactions, building blocks and synthetic methods have been developed and a broad variety of CMPs with different structures and specific properties have been synthesized, driving the rapid growth of the field. CMPs are unique in that they allow the complementary utilization of π-conjugated skeletons and nanopores for functional exploration; they have shown great potential for challenging energy and environmental issues, as exemplified by their excellent performance in gas adsorption, heterogeneous catalysis, light emitting, light harvesting and electrical energy storage. This review describes the molecular design principles of CMPs, advancements in synthetic and structural studies and the frontiers of functional exploration and potential applications.

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Section: Introductionmentioning

confidence: 99%

Conjugated microporous polymers: design, synthesis and application

et al. 2013

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“…In connection with our previous programs on synthesis of organic compounds, [20][21][22][23] in this work, we wish to report a simple and convenient synthesis of octahydroquinazolinones/thiones 4 by reaction of aromatic aldehyde 1, urea/thiourea 2, and cyclic 1,3-dione 3, in the presence of catalytic amount of In(OTf) 3 under solvent-free conditions (Scheme 1). The yield of products was good to excellent without the formation of octahydoxanthenes 5, which is the major product of the procedure reported by the literature.…”

Section: Resultsmentioning

confidence: 99%

Indium(III) Trifluoromethanesulfonate: a Reusable Catalyst for the Sol-vent-free Synthesis of some Quinazolinones/thiones

Karami¹,

Khodabakhshi²,

Karami³

2014

Croat. Chem. Acta

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Abstract. An environmentally friendly and clean procedure gives octahydroquinazolinones/thiones by a simple Biginelli condensation of urea/thiourea, aromatic aldehydes, and cyclic 1,3-diones in the presence of indium(III) trifluoromethanesulfonate (In(OTf) 3 ) in solventless conditions. This method has advantages such as avoidance of the organic solvents, high yield of pure products without any by-product, short reaction times and operational simplicity.(doi: 10.5562/cca2087)

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“…Karami and co‐worker studied the synthesis of various phenazines and quinoxalines using magnesium sulfate heptahydrate (MgSO 4 ⋅7H 2 O) as an effective, cheap and non‐toxic catalyst based on the condensation of 1,2‐dicarbonyl compounds with o ‐phenylenediamines . To prove the general applicability of the method few azatriphenylene derivatives have been synthesized by the reaction of 9,10‐phenanthrenequinone ( 7 ) with corresponding 1,2‐diamines ( 42 ).…”

Section: Synthetic Approaches Towards Azatriphenylene Derivatives:mentioning

confidence: 99%

“…In addition, this methodology is also applicable for the synthesis of sterically hindered azatriphenylene derivative such as tetrapyrido- Karami and co-worker studied the synthesis of various phenazines and quinoxalines using magnesium sulfate heptahydrate (MgSO 4 ⋅7H 2 O) as an effective, cheap and non-toxic catalyst based on the condensation of 1,2-dicarbonyl compounds with o-phenylenediamines. [36] To prove the general applicability of the method few azatriphenylene derivatives have been synthesized by the reaction of 9,10-phenanthrenequinone (7) with corresponding 1,2-diamines (42). In addition, it was found that 1,2-pyridinediamine underwent the condensation with compound 42 to produce dibenzo [f,h] (46) in 77 % yield.…”

Section: Synthesis Of Di-azatriphenylenesmentioning

confidence: 99%

Mono‐ and Polyazatriphenylene‐Based Ligands: An Updated Library of Synthetic Strategies (2001–2018)

et al. 2018

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This review surveys the most useful strategies for the synthesis of azatriphenylenes. Azatriphenylene derivatives are of considerable interest due to their promising photophysical and coordinating properties and to their presence in the composition of natural products. These scaffolds have shown ability as photoluminescent chemosensors for organic anions and nitroaromatic compounds. The straight‐forward construction of an azatriphenylene moiety from the easily available chemicals is desirable due to its tremendous use in the various branches of chemistry and material sciences. These target compounds can also be used as components of (metallo)intercalators (insertors) for biological studies as well as photoluminescent emitters. Here we report a review on the synthesis of these scaffolds employing different strategies such as cyclocondensation reaction, Friedel–Crafts reaction, Westphal condensation reaction, Chichibabin‐type condensation reaction, coupling reaction, intermolecular homocoupling‐cyclotrimerization reaction, cycloaddition reaction, Pomeranz–Fritsch cyclization and intramolecular cyclization reaction. In addition, a brief historical approach has also been discussed. This review will cover the synthetic routes to afford azatriphenylene derivatives broadly including mono‐, di‐, tri‐, tetra, and hexa‐azatriphenylenes. As a consequence, this review will contribute ample and updated information on the synthesis of this class of compounds.

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A facile synthesis of phenazine and quinoxaline (new 1,4-benzo diazine) derivatives using magnesium sulfate heptahydrate as a catalyst

Cited by 13 publications

References 10 publications

Conjugated microporous polymers: design, synthesis and application

Conjugated microporous polymers: design, synthesis and application

Indium(III) Trifluoromethanesulfonate: a Reusable Catalyst for the Sol-vent-free Synthesis of some Quinazolinones/thiones

Mono‐ and Polyazatriphenylene‐Based Ligands: An Updated Library of Synthetic Strategies (2001–2018)

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