Sonochemistry in an organocatalytic domino reaction: an expedient multicomponent access to structurally functionalized dihydropyrano[3,2-<i>b</i>]pyrans, spiro-pyrano[3,2-<i>b</i>]pyrans, and spiro-indenoquinoxaline-pyranopyrans under ambient conditions

Borah, Biplob; Bora, Jahnu; Ramesh, P.; Chowhan, L. Raju

doi:10.1039/d2ra01917e

Cited by 29 publications

(20 citation statements)

References 88 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Recognizing all these limitations and encouraged by our aforementioned results, as well as our ongoing interest in the multicomponent synthesis of medicinally privileged heterocycles 100 – 103 , we performed a domino three-component reaction between 1 equivalent of salicylaldehyde 8a and 2 equivalent of 5,5-dimethyl cyclohexane-1,3-dione 3a by employing water ( η = 0.25 μL/mg) as the liquid assisted additives in presence of 5 mol% of TsOH⋅H 2 O as the Brønsted acid catalyst under mechanochemical grinding conditions. To our delight, the reaction afforded the corresponding 9-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-en-1-yl)-3,3-dimethyl-2,3,4,9-tetrahydro-1 H -xanthen-1-one, 9a in 96% yield within 8 min.…”

Section: Resultsmentioning

confidence: 99%

Brønsted acid catalyzed mechanochemical domino multicomponent reactions by employing liquid assisted grindstone chemistry

Borah

Swain

Patat

et al. 2023

Sci Rep

Self Cite

View full text Add to dashboard Cite

Here, we have demonstrated a metal-free energy-efficient mechanochemical approach for expedient access to a diverse set of 2-amino-3-cyano-aryl/heteroaryl-4H-chromenes, tetrahydrospiro[chromene-3,4′-indoline], 2,2′-aryl/heteroarylmethylene-bis(3-hydroxy-5,5-dimethylcyclohex-2-enone) as well as tetrahydro-1H-xanthen-1-one by employing the reactivity of 5,5-dimethylcyclohexane-1,3-dione/cyclohexane-1,3-dione with TsOH⋅H2O as Brønsted acid catalyst under water-assisted grinding conditions at ambient temperature. The ability to accomplish multiple C–C, C=C, C–O, and C–N bonds from readily available starting materials via a domino multicomponent strategy in the absence of metal-catalyst as well as volatile organic solvents with an immediate reduction in the cost of the transformation without necessitates complex operational procedures, features the significant highlights of this approach. The excellent yield of the products, broad functional group tolerances, easy set-up, column-free, scalable synthesis with ultralow catalyst loading, short reaction time, waste-free, ligand-free, and toxic-free, are other notable advantages of this approach. The greenness and sustainability of the protocol were also established by demonstrating several green metrics parameters.

show abstract

Section: Resultsmentioning

confidence: 99%

Brønsted acid catalyzed mechanochemical domino multicomponent reactions by employing liquid assisted grindstone chemistry

Borah

Swain

Patat

et al. 2023

Sci Rep

Self Cite

View full text Add to dashboard Cite

show abstract

“…Recognizing all these limitations and encouraged by our aforementioned results, as well as our ongoing interest in the multicomponent synthesis of medicinally privileged heterocycles, [100][101][102][103] we performed a domino three-component reaction between 1 equivalent of salicylaldehyde 8a and 2 equivalent of 5,5dimethyl cyclohexane-1,3-dione 3a by employing water ( = 0.25 µL/mg) as the liquid assisted additives in presence of 5 mol% of TsOH.H 2 O as the Brønsted acid catalyst under mechanochemical grinding conditions. To our delight, the reaction afforded the corresponding 9-(2-hydroxy-4,4-dimethyl-6oxocyclohex-1-en-1-yl)-3,3-dimethyl-2,3,4,9-tetrahydro-1H-xanthen-1-one, 9a in 96% yield within 8 minutes.…”

Section: Resultsmentioning

confidence: 99%

Liquid assisted Grindstone Chemistry: An eco-friendly scalable approach for diverse Brønsted acid-catalyzed mechanochemical domino multicomponent reactions by employing the reactivity of cyclic 1,3-diketones at ambient conditions

Borah

Swain

Patat

et al. 2022

Preprint

Self Cite

View full text Add to dashboard Cite

Here, we have demonstrated a metal-free energy-efficient mechanochemical approach for expedient access to a diverse set of 2-amino-3-cyano-aryl/heteroaryl-4H-chromenes, tetrahydrospiro[chromene-3,4´-indoline], 2,2'-aryl/heteroarylmethylene-bis(3-hydroxy-5,5-dimethylcyclohex-2-enone) as well as tetrahydro-1H-xanthen-1-one by employing the reactivity of 5,5-dimethylcyclohexane-1,3-dione/cyclohexane-1,3-dione with TsOH.H2O as Brønsted acid catalyst under water-assisted grinding conditions at ambient temperature. The ability to accomplish multiple C-C, C = C, C-O, and C-N bonds from readily available starting materials via a domino multicomponent strategy in the absence of metal-catalyst as well as volatile organic solvents with an immediate reduction in the cost of the transformation without necessitates complex operational procedures, features the significant highlights of this approach. The excellent yield of the products, broad functional group tolerances, easy set-up, column-free, scalable synthesis with ultralow catalyst loading, short reaction time, waste-free, ligand-free, and toxic-free, are other notable advantages of this approach. The greenness and sustainability of the protocol were also established by demonstrating several green metrics parameters.

show abstract

“…Recently, multi-component reactions (MCRs), which allow the formation of multiple bonds in a single operation, have been demonstrated as a promising tool for the creation of diverse molecular structures with enhanced efficiency, reduced waste, and high atom economy from easily accessible simple and inexpensive starting materials by effortless mixing of the reactant ( Rotstein et al, 2014 ; Borah et al, 2022c ). The ability to accomplish the requisite products in “one-pot” by operationally simple workup procedure without using complex purification techniques and avoiding the isolation of the reaction intermediate features multi-component reaction, a powerful strategy for green or sustainable synthesis ( Borah et al, 2022b ).…”

Section: Synthesis Of Quinazolinones From Multi-component Organocatal...mentioning

confidence: 99%

Recent advances and prospects in the organocatalytic synthesis of quinazolinones

et al. 2022

Self Cite

View full text Add to dashboard Cite

Quinazolinone, a bicyclic compound, comprises a pyrimidine ring fused at 4´ and 8´ positions with a benzene ring and constitutes a substantial class of nitrogen-containing heterocyclic compounds on account of their frequent existence in the key fragments of many natural alkaloids and pharmaceutically active components. Consequently, tremendous efforts have been subjected to the elegant construction of these compounds and have recently received immense interest in synthetic and medicinal chemistry. The domain of synthetic organic chemistry has grown significantly over the past few decades for the construction of highly functionalized therapeutically potential complex molecular structures with the aid of small organic molecules by replacing transition-metal catalysis. The rapid access to this heterocycle by means of organocatalytic strategy has provided new alternatives from the viewpoint of synthetic and green chemistry. In this review article, we have demonstrated a clear presentation of the recent organocatalytic synthesis of quinazolinones of potential therapeutic interests and covered the literature from 2015 to date. In addition to these, a clear presentation and understanding of the mechanistic aspects, features, and limitations of the developed reaction methodologies have been highlighted.

show abstract

Sonochemistry in an organocatalytic domino reaction: an expedient multicomponent access to structurally functionalized dihydropyrano[3,2-b]pyrans, spiro-pyrano[3,2-b]pyrans, and spiro-indenoquinoxaline-pyranopyrans under ambient conditions

Abstract: Amino-substituted 4,8-dihydropyrano[3,2-b]pyran-3-carbonitriles, and spiro[indoline-3,4′-pyrano[3,2-b]pyran]-3-carbonitrile/carboxylate derivatives has been synthesised under ultrasound irradiation in aqueous ethanolic solution at rt.

Cited by 29 publications

References 88 publications

Brønsted acid catalyzed mechanochemical domino multicomponent reactions by employing liquid assisted grindstone chemistry

Brønsted acid catalyzed mechanochemical domino multicomponent reactions by employing liquid assisted grindstone chemistry

Liquid assisted Grindstone Chemistry: An eco-friendly scalable approach for diverse Brønsted acid-catalyzed mechanochemical domino multicomponent reactions by employing the reactivity of cyclic 1,3-diketones at ambient conditions

Recent advances and prospects in the organocatalytic synthesis of quinazolinones

Contact Info

Product

Resources

About