Green chemistry approach to synthesis of some new trifluoromethyl containing tetrahydropyrimidines under solvent free conditions

Khunt, Ranjan C.; Akbari, J. D.; Manvar, Atul; Tala, S. D.; Dhaduk, M. F.; Joshi, H. S.; Shah, Anamik

doi:10.3998/ark.5550190.0009.b27

Cited by 18 publications

(4 citation statements)

References 6 publications

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“…The same rection was performed in refluxing ethanol, containing metallic sodium, for 6-7 h, furnishing the products in 4-78% yields. 312 Recently, Khunt et al 313 developed a microwave-assisted process for the fast preparation of tetrahydropyrimidines 167 and tetrahydrothiopyrimidines 168 employing equimolar amounts of neat 1,3-dicarbonyl compounds 166, different aromatic aldehydes 21, and urea 24 (or thiourea 25) (Scheme 51). The reaction was carried out in microwave equipment for synthesis, and the products 167 and 168 were obtained in high purity (>90%), in 78-85% yields, and without any side products in every run.…”

Section: Pyrimidinesmentioning

confidence: 99%

Solvent-Free Heterocyclic Synthesis

et al. 2009

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Clarissa P. Frizzo was born in Ivora ´, Rio Grande do Sul state, Brazil, in 1983. She received her undergraduate degree in Pharmacy from the Federal University of Santa Maria in 2005, and in 2007 she obtained her M.Sc. degree from the Federal University of Santa Maria, under the supervision of Professor Marcos A. P. Martins, working with the use of ionic liquids in the synthesis of heterocycles. She started her Ph.D. studies under the supervision of Professor Marcos A. P. Martins, and currently she is focusing on her Sandwich Ph.D. in the Universidade Nacional de Educacio ´n a Distancia in Spain, under the guidance of Professor Rosa M. Claramunt Vallespı ´, where she is studying the supramolecular structure of heterocycles. Dayse das Neves Moreira was born in Canguc ¸u, Rio Grande do Sul state, Brazil, in 1984. She received her undergraduate degree in Chemistry from the Federal University of Pelotas, RS, in 2006, and in 2008 she received her M.S. degree, from the Federal University of Santa Maria, RS, Brazil, working under the direction of Professor Marcos A. P. Martins, working with the use of ionic liquids in the synthesis of heterocycles. Currently, she is a Ph.D. student with Professor Marcos A. P. Martins in the Department of Chemistry of the Federal University of Santa Maria. Her major research interest is to develop new methodologies to synthesize heterocyclic compounds. Lilian Buriol was born in Santa Izabel do Oeste, Parana ´(PR) state, Brazil, in 1984. She received her undergraduate degree in Chemistry from the State University of Centro-Oeste (PR). In 2008, she completed her M.S. degree at the same university under the supervision of Professor Yohandra R. Torres, working with oil and ethanol extracts of propolis. After that, she started her Ph.D. studies in the Department of Chemistry of the Federal University of Santa Maria under the supervision of Professor Marcos A. P. Martins. Her research interest is to develop new methodologies to synthesize heterocyclic compounds along the lines of green chemistry.

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Section: Pyrimidinesmentioning

confidence: 99%

Solvent-Free Heterocyclic Synthesis

et al. 2009

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“…In a different example, the catalyzed reaction is described to proceed with yields ranging from poor to excellent at 25 °C, 43 but long reaction times were needed to achieve such yields. Alternative methodologies such as microwave irradiation 44 and ultrasound 45 have also been reported with yields ranging from reasonable to good. The application of some catalysts for the Biginelli reaction under microwave 46 or ultrasound 47 conditions has been already described, and improved yields could be achieved when compared with those catalyst-free versions.…”

Section: ■ Introductionmentioning

confidence: 99%

Facts, Presumptions, and Myths on the Solvent-Free and Catalyst-Free Biginelli Reaction. What is Catalysis for?

et al. 2014

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The current manuscript describes the role and importance of catalysis and solvent effects for the Biginelli multicomponent reaction. The overwhelming number of new catalysts and conditions recently published for the Biginelli synthesis, including in some manuscripts entitled "catalyst-free" and/or "solvent-free" have incentivized controversies and hot debates regarding the importance of developing new catalysts and reaction conditions to perform this very important multicomponent reaction. These so-called "catalyst-free" reports have generated much confusion in the field, requiring urgent elucidations. In this manuscript, we exemplify, demystify, and discuss the crucial role of catalysis, solvent effects, mechanisms, kinetics, facts, presumptions, and myths associated with the Biginelli reaction aiming to avoid current and future confusion and to stimulate new approaches.

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“…[236] Khunt et al revealed the microwave assisted solvent-free synthesis of tetrahydropyrimidones/thiones 411 via modified Biginelli approach from 1,1,1-trifluoro-4-(4-methoxyphenyl)butane-2,4-dione 1, substituted benzaldehydes 138 and thiourea/ urea 221/313 (Scheme 140). [237] Faster reaction rates, neat reaction conditions, and excellent yields were advantages of this protocol.…”

Section: Putilova Et Al Reported the Use Of Ionic Liquid [Bmim][bfmentioning

confidence: 98%

Trifluoromethyl‐β‐dicarbonyls as Versatile Synthons in Synthesis of Heterocycles

Sumran,

Jain,

Kumar

et al. 2024

Chemistry A European J

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Trifluoromethyl group relishes a privileged position in the realm of medicinal chemistry because its incorporation into organic molecules often enhances the bioactivity by altering pharmacological profile of molecule. Trifluoromethyl‐β‐dicarbonyls have emerged as pivotal building blocks in synthetic organic chemistry due to their facile accessibility, stability and remarkable versatility. Owing to presence of nucleophilic and electrophilic sites, they offer multifunctional sites for the reaction. This review covers a meticulous exploration of their multifaceted role, encompassing an in‐depth analysis of mechanism, extensive scope, limitations and wide‐ranging applications in diverse organic synthesis, covering the literature from the 21st century. This comprehensive review encapsulates the applications of trifluoromethyl‐β‐dicarbonyls and their synthetic equivalents as precursors of complex and diverse heterocyclic scaffolds, fused heterocycles and spirocyclic compounds having medicinal and material importance. Their potent synthetic utility in cyclocondenation reactions with binucleophiles, cycloaddition reactions, C‐C bond formations, asymmetric multicomponent reactions using classical/solvent‐free/catalytic synthesis have been presented. Influence of unsymmetrical trifluoromethyl‐β‐diketones on regioselectivity of transformation is also reviewed. This review will benefit the synthetic and pharmaceutical communities to explore trifluoromethyl‐β‐dicarbonyls as trifluoromethyl building blocks for fabrication of heterocyclic scaffolds having implementation into drug discovery programs in the imminent future.

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Green chemistry approach to synthesis of some new trifluoromethyl containing tetrahydropyrimidines under solvent free conditions

Cited by 18 publications

References 6 publications

Solvent-Free Heterocyclic Synthesis

Solvent-Free Heterocyclic Synthesis

Facts, Presumptions, and Myths on the Solvent-Free and Catalyst-Free Biginelli Reaction. What is Catalysis for?

Trifluoromethyl‐β‐dicarbonyls as Versatile Synthons in Synthesis of Heterocycles

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