Enamines and their variants as intermediates for synthesis of aza-heterocycles with applications in MCRs

Magoo, Devanshi; Aggarwal, Komal; Gupta, S. R.; Meena, Kalawati

doi:10.1016/j.tet.2021.132545

Cited by 14 publications

(9 citation statements)

References 153 publications

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“…Multicomponent reactions (MCRs) can connect three or more compounds in a single step to synthesize target molecules [1–6] . MCRs are atom‐ and step‐economical; hence, they are useful tools for synthesizing dyes, functional polymers, and physiologically active compounds [7–12] .…”

Section: Introductionmentioning

confidence: 99%

“…Multicomponent reactions (MCRs) can connect three or more compounds in a single step to synthesize target molecules. [1][2][3][4][5][6] MCRs are atom-and step-economical; hence, they are useful tools for synthesizing dyes, functional polymers, and physiologically active compounds. [7][8][9][10][11][12] Among various MCRs, the Povarov reaction is a facile synthesis method for producing nitrogencontaining aromatic compounds from anilines, aldehydes, and dienophiles, such as electron-rich alkenes and alkynes.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of Triazatriphenylene Derivative Through Multi‐Component Reaction of Aryl‐amine, Aldehyde, and Alkyne

et al. 2023

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The Povarov reaction is a representative multicomponent reaction used for synthesizing nitrogen‐containing aromatic compounds from aromatic amines, aldehydes, and dienophiles, such as electron‐rich alkenes and alkynes. In this study, we investigated a triple Povarov reaction of 1,3,5‐triaminobenzne with aromatic aldehydes and phenylacetylene to obtain triazatriphenylene derivatives. Reactions with arylaldehydes containing electron‐donating groups proceeded smoothly to provide triazatriphenylene derivatives. In contrast, reactions with arylaldehydes containing electron‐withdrawing groups resulted in low yields. Reactions with electron‐rich arylaldehydes are probably more favorable in terms of high stability of imine intermediates and smooth electrophilic cyclization. Single‐crystal X‐ray structure analysis revealed that the aryl groups derived from the aldehydes had small dihedral angles between with the triazatriphenylene core. The derivative with tertiary butyl groups (tBu‐TaT) had a high glass transition temperature, while that without tertiary butyl groups (H‐TaT) had a lower highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) level and served as an efficient hole‐blocking material with better electron transport properties than those of tBu‐TaT. This study provides insights into the scope and limitations of the multicomponent reactions based on the Povarov reaction, substituent dependence on the crystal structures, and physical properties of π‐extended nitrogen‐containing aromatic compounds.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis of Triazatriphenylene Derivative Through Multi‐Component Reaction of Aryl‐amine, Aldehyde, and Alkyne

et al. 2023

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“…Some traditional MCRs, which have been known for more than a century, still have their reaction mechanisms hotly debated [14] . Actually, it is possible to find reviews of almost every aspects of MCRs [15–21] . However, despite the huge development of MCRs, in particular in the last two decades, much is still to be learned.…”

Section: Introductionmentioning

confidence: 99%

“…[14] Actually, it is possible to find reviews of almost every aspects of MCRs. [15][16][17][18][19][20][21] However, despite the huge development of MCRs, in particular in the last two decades, much is still to be learned.…”

Section: Introductionmentioning

confidence: 99%

Solvent Screening Is Not Solvent Effect: A Review on the Most Neglected Aspect of Multicomponent Reactions

2022

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In the current Perspective article, we critically review and discuss the importance of solvent effects on multicomponent reactions, likely the most neglected aspect in this research field. Although solvent-free reactions may be desirable sometimes, most multicomponent reactions still require a solvent to properly promote them. This requirement makes the knowledge of all drawbacks and advantages of each solvent a central issue when trying to optimize multicomponent reactions. Yet, only a few studies with actual evidence of solvent effects on these key reactions have been published. For the quantitative effects of solvents, studies are even scarcer. In this Perspective, we argue that greater efforts should be directed to such fundamental studies.

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“…Various modifications of this method were also developed and often used when the classic Hantzsch synthesis failed. Frequently, enamines are used instead of active methylene carbonyl compound and a source of ammonia [18]. Aldehydes can be condensed with active methylene compounds leading to α,β-unsaturated ketones.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Characterisation of 1,1′-{[3,5-Bis(dodecyloxy-carbonyl)-4-(thiophen-3-yl)-1,4-dihydropyridine-2,6-diyl]bis-(methylene)}bis(pyridin-1-ium) Dibromide

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et al. 2021

Molbank

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In the present work, construction of double-charged cationic amphiphilic 1,1′-{[3,5-bis(dodecyl¬oxy-carbonyl)-4-(thiophen-3-yl)-1,4-dihydropyridine-2,6-diyl]bis-(methylene)}bis(pyridin-1-ium) dibromide (7) was performed in four steps. Dodecyl 3-oxobutanoate (1) was condensed with thiophene-3-carbaldehyde (2) which was necessary for Hantzsch cyclisation dodecyl (E/Z)-3-oxo-2-(thiophen-3-ylmethylene)butanoate (3). Two-component Hantzsch type cyclisation of dodecyl (E/Z)-3-aminobut-2-enoate (4) and dodecyl (E/Z)-3-oxo-2-(thiophen-3-ylmethylene)butanoate (3) gave 3,5-bis(dodecyloxycarbonyl)-2,6-dimethyl-4-(thiophen-3-yl)-1,4-dihydropyridine (5). Bromination of compound 5 followed by nucleophilic substitution of bromine with pyridine gave the desired cationic amphiphilic 1,4-dihydropyridine 7. The obtained target compound 7 and new intermediates 3, 5 and 6 were fully characterised by IR, UV, 1H NMR, 13C NMR, HRMS or microanalysis. Characterisation of nanoparticles formed by the cationic 1,4-dihydropyridine 7 in an aqueous solution was performed by DLS measurements.

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Enamines and their variants as intermediates for synthesis of aza-heterocycles with applications in MCRs

Cited by 14 publications

References 153 publications

Synthesis of Triazatriphenylene Derivative Through Multi‐Component Reaction of Aryl‐amine, Aldehyde, and Alkyne

Synthesis of Triazatriphenylene Derivative Through Multi‐Component Reaction of Aryl‐amine, Aldehyde, and Alkyne

Solvent Screening Is Not Solvent Effect: A Review on the Most Neglected Aspect of Multicomponent Reactions

Synthesis and Characterisation of 1,1′-{[3,5-Bis(dodecyloxy-carbonyl)-4-(thiophen-3-yl)-1,4-dihydropyridine-2,6-diyl]bis-(methylene)}bis(pyridin-1-ium) Dibromide

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