A mechanistic investigation of Biginelli reaction under base catalysis

Raj, Monika; Rao, H. Surya Prakash; Manjunatha, Sulur G.; Sridharan, R.; Nambiar, Sudhir; Keshwan, Jaikumar; Rappai, Jayan; Bhagat, Sagar; Shwetha, B.S.; Hegde, Dinesh; Santhosh, U.

doi:10.1016/j.tetlet.2011.05.011

Cited by 15 publications

(4 citation statements)

References 37 publications

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“…Under simple optimization, 86% yield of DHPM was obtained (Table ). As shown in Table , CuCl and methylisobutyryl acetate have obvious effect on this reaction rather than H 2 SO 4 and urea .…”

Section: Resultsmentioning

confidence: 86%

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Efficient Construction of the Nucleus of Rosuvastatin Calcium

Zhou

Lin

Xing

et al. 2016

Journal of Heterocyclic Chem

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A novel and efficient five‐step synthetic route, including a Biginelli reaction, dehydrogenation, chlorination, sulfonamidation, and reduction, for the core of Rosuvastatin was established. All steps were systematically studied. Tert‐butylhydroperoxide aqueous solution was applied in the dehydrogenation instead of nitric acid. N,N‐dimethylaniline was employed as a catalyst to accelerate the chlorination proceeding smoothly, and its catalytic mechanism is discussed. In the sulfonamidation, the conversion of compound 5 was obviously improved by use of NaH and acetonitrile. In addition, two sulfonamidation side products 6 and 7 were detected and isolated. Thus, under the optimized reaction conditions, the target product was obtained in 60.4% total yield, much higher than the reported yield (36.4%).

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Section: Resultsmentioning

confidence: 86%

“…), but received little attention. Until 2003, owing to the pharmaceutical importance associated with the derivatives of this privileged heterocyclic core, DHPMs have surged rapidly .…”

Section: Introductionmentioning

confidence: 99%

Efficient Construction of the Nucleus of Rosuvastatin Calcium

Zhou

Lin

Xing

et al. 2016

Journal of Heterocyclic Chem

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“…DHPMs are heterocyclic compounds with a wide array of applications, especially in medical, biomedical, and pharmaceutical fields. , As such, there is growing interest in promoting the Biginelli reaction using green and efficient methods. Although basic catalysts are less used in this reaction, there are several examples of the base-mediated Biginelli reaction in the literature. − Therefore, we decided to use TAPT-Bd(SO 3 H) 2 -POP (containing acidic and basic groups) and TAPT-Bd-POP (containing only basic groups) as catalysts in this reaction. The conversions and DHPM selectivities of the triazene POP-catalyzed Biginelli reactions between aromatic aldehydes, ethyl acetoacetate, and urea are shown in Table .…”

Section: Resultsmentioning

confidence: 99%

Triazene-Linked Porous Organic Polymers for Heterogeneous Catalysis and Pollutant Adsorption

Machado,

Valente,

Serra

et al. 2024

ACS Appl. Polym. Mater.

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Porous organic polymers (POPs) are highly promising materials for heterogeneous catalysis and pollutant adsorption from aqueous medium due to their high surface area, permanent porosity, monomer diversity, and synthetic versatility. In this work, two triazene-linked POPs were synthesized under mild reaction conditions, via the diazo-coupling reaction, between 1,3,5-tris(4-aminophenyl) triazine and benzidine (TAPT-Bd-POP) or 4,4′-diamino-[1,1′-biphenyl]-2,2′-disulfonic acid (TAPT-Bd-(SO 3 H) 2 -POP), the latter containing intrapore sulfonic groups. These POPs, containing triazene (−N�N−NH−) linkages with interesting properties, have been overlooked as a method for organic polymer synthesis. The polymers exhibited BET average pore diameters of around 10 nm, BET surface areas of up to 133 ± 2.0 m 2 g −1 , and thermal stability of up to 333 °C. TAPT-Bd-POP and TAPT-Bd(SO 3 H) 2 -POP were evaluated as catalysts for the metal-free Henry, Knoevenagel, and multicomponent one-pot Biginelli reactions, between aromatic aldehydes and nitromethane, ethyl cyanoacetate, and urea/ethyl acetoacetate, respectively, with moderate to almost full conversions. Both POPs were further used as adsorbents for the removal of methylene blue, crystal violet, phenol red, phenol, Cu(II), and Cr(VI), with maximum adsorption capacities up to 953 ± 71 mg g −1 for the adsorption of methylene blue. These results show the versatility of these polymers for heterogeneous catalysis and environmental remediation.

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“…The reaction mechanism was discussed in various experimental and theoretical studies. ,,,,,− De Souza et al performed infusion electrospray ionization mass spectrometry (ESI-MS) to identify intermediates involved in the reaction. Different intermediates from all three routes were found.…”

Section: Introductionmentioning

confidence: 99%

The Biginelli Reaction Is a Urea-Catalyzed Organocatalytic Multicomponent Reaction

et al. 2015

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The recently developed artificial force induced reaction (AFIR) method was applied to search systematically all possible multicomponent pathways for the Biginelli reaction mechanism. The most favorable pathway starts with the condensation of the urea and benzaldehyde, followed by the addition of ethyl acetoacetate. Remarkably, a second urea molecule catalyzes nearly every step of the reaction. Thus, the Biginelli reaction is a urea-catalyzed multicomponent reaction. The reaction mechanism was found to be identical in both protic and aprotic solvents.

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A mechanistic investigation of Biginelli reaction under base catalysis

Cited by 15 publications

References 37 publications

Efficient Construction of the Nucleus of Rosuvastatin Calcium

Efficient Construction of the Nucleus of Rosuvastatin Calcium

Triazene-Linked Porous Organic Polymers for Heterogeneous Catalysis and Pollutant Adsorption

The Biginelli Reaction Is a Urea-Catalyzed Organocatalytic Multicomponent Reaction

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