Are Multicomponent Strecker Reactions of Diketones with Diamines under High Pressure Amenable to Heterocyclic Synthesis?

Matsumoto, Kiyoshi; Kumamoto, Koji; Iida, Hiroki; Hamana, Hiroshi; Kotsuki, Hiyoshizo

doi:10.3987/com-05-s(k)69

Cited by 12 publications

(7 citation statements)

References 14 publications

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“…This reaction is therefore difficult under conventional thermal condition without any catalyst. This is consistent with many experimental reports. − However, under mechanochemical conditions, mechanical action can generate sufficient energy (on the order of eV) locally . Therefore, both the stepwise and concerted paths are possible during grinding.…”

Section: Resultssupporting

confidence: 91%

“…The quinoxaline structure is an important building block of organic semiconductors and pharmacologically active compounds . DBPZ has been synthesized in various ways. − Conventional syntheses require both a solvent and a catalyst. More specifically, Brønsted acids, ,,,,,,,,, metal oxide nanoparticles, ,,,,,,,,,, and ionic liquids ,,,,, have been used.…”

Section: Introductionmentioning

confidence: 99%

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Force-Induced Dissolution of Imaginary Mode in Mechanochemical Reaction: Dibenzophenazine Synthesis

et al. 2019

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Dibenzophenazine was recently synthesized mechanochemically at a high yield. On the basis of experimental kinetics and theoretical vibronic coupling density analysis, this efficient synthesis has been expected to involve two types of reaction mechanisms. In this study, the reaction pathways, including the catalytic effect of water, are determined using density functional theory. The lowest-energy path involves stepwise formation of two C−N bonds, and a concerted path with a higher barrier is also found. The highest-energy point along the latter path is not a transition state but a higher-order saddle point. Therefore, the concerted path is not generally accepted as a reaction path. However, even a small mechanical force dissolves imaginary frequencies so that the higher-order saddle point is changed to a transition state. This mechanical dissolution of imaginary frequencies is a new feature of theoretical mechanochemistry.

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Section: Resultssupporting

confidence: 91%

Section: Introductionmentioning

confidence: 99%

Force-Induced Dissolution of Imaginary Mode in Mechanochemical Reaction: Dibenzophenazine Synthesis

et al. 2019

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“…For some MCRs, heating is imperative, whereas for others, it is just a matter of productivity associated with the energy demand. MCRs carried out under high-pressure conditions are not commonly described, although some examples can be found in the literature [ 97 , 98 , 99 , 100 , 101 ]. Considering that MCRs typically have sequences of elementary equilibrium stages and that thermodynamic adduct formation, or release of stable subproducts (e.g., water), favors the shifting of these stages toward the final desired adduct, high-energy-demanding multicomponent transformations can be avoided by employing catalysis.…”

Section: Catalyst-free Mcrs and Reasons To Use Catalystsmentioning

confidence: 99%

Catalytic Approaches to Multicomponent Reactions: A Critical Review and Perspectives on the Roles of Catalysis

2021

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In this review, we comprehensively describe catalyzed multicomponent reactions (MCRs) and the multiple roles of catalysis combined with key parameters to perform these transformations. Besides improving yields and shortening reaction times, catalysis is vital to achieving greener protocols and to furthering the MCR field of research. Considering that MCRs typically have two or more possible reaction pathways to explain the transformation, catalysis is essential for selecting a reaction route and avoiding byproduct formation. Key parameters, such as temperature, catalyst amounts and reagent quantities, were analyzed. Solvent effects, which are likely the most neglected topic in MCRs, as well as their combined roles with catalysis, are critically discussed. Stereocontrolled MCRs, rarely observed without the presence of a catalytic system, are also presented and discussed in this review. Perspectives on the use of catalytic systems for improved and greener MCRs are finally presented.

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“…Kotsuki and Matsumoto prepared dibenzo[ a,c ]phenazine ( 88 ) by the reaction of 9,10‐phenanthrenequinone ( 7 ) with o ‐phenylenediamine ( 49 ) in presence of Me 3 SiCN (TMSCN) (Scheme ) . Indeed, the reaction has proven to proceed without TMSCN at room temperature, probably due to aromatic stabilization of the azatriphenylene derivative.…”

Section: Synthetic Approaches Towards Azatriphenylene Derivatives:mentioning

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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Are Multicomponent Strecker Reactions of Diketones with Diamines under High Pressure Amenable to Heterocyclic Synthesis?

Cited by 12 publications

References 14 publications

Force-Induced Dissolution of Imaginary Mode in Mechanochemical Reaction: Dibenzophenazine Synthesis

Force-Induced Dissolution of Imaginary Mode in Mechanochemical Reaction: Dibenzophenazine Synthesis

Catalytic Approaches to Multicomponent Reactions: A Critical Review and Perspectives on the Roles of Catalysis

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

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