A microwave-mediated catalyst- and solvent-free regioselective Biginelli reaction in the synthesis of highly functionalized novel tetrahydropyrimidines

Harikrishnan, Palani Sokkan; Rajesh, Stephen Michael; Perumal, S.; Almansour, Abdulrahman I.

doi:10.1016/j.tetlet.2012.12.034

Cited by 36 publications

(7 citation statements)

References 40 publications

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“…[52] A series of ethyl 2-oxo/thio-4-aryl-6-(arylsulfonylmethyl)-1,2,3,4-tetrahydropyrimidine-5-carboxylates was synthesized under optimized conditions in good to excellent yield. [52] A series of ethyl 2-oxo/thio-4-aryl-6-(arylsulfonylmethyl)-1,2,3,4-tetrahydropyrimidine-5-carboxylates was synthesized under optimized conditions in good to excellent yield.…”

Section: Mw Irradiationmentioning

confidence: 99%

“…When the reaction of 6-(2-morpholinovinyl)-1,3-dimethyl uracil with benzaldehyde and urea was performed under identical conditions for 12 min using MWs, 1,3-dimethyl-5-phenyl-pyrido[4,3- Perumal et al reported regioselective Biginelli reactions under SF-CF conditions and MW irradiation. [52] A series of ethyl 2-oxo/thio-4-aryl-6-(arylsulfonylmethyl)-1,2,3,4-tetrahydropyrimidine-5-carboxylates was synthesized under optimized conditions in good to excellent yield. Notably, under MW irradiation, the reactions were considerably faster compared to thermal conditions (Scheme 16).…”

Section: Mw Irradiationmentioning

confidence: 99%

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Solvent‐Free and Catalysts‐Free Chemistry: A Benign Pathway to Sustainability

Gawande¹,

Bonifácio²,

Luque³

et al. 2013

ChemSusChem

278

122

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In the past decade, alternative benign organic methodologies have become an imperative part of organic syntheses and chemical reactions. The various new and innovative sustainable organic reactions and methodologies using no solvents or catalysts and employing alternative energy inputs such as microwaves, sonication, conventional and room temperature heating conditions, mechanochemical mixing, and high-speed ball milling are discussed in detail. Environmentally benign and pharmaceutically important reactions such as multicomponent, condensation, and Michael addition reactions; ring opening of epoxides; and oxidation and other significant organic reactions are discussed. An overview of benign reactions through solvent- and catalyst-free (SF-CF) chemistry and a critical perspective on emerging synergies between SF-CF organic reactions are discussed.

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Section: Mw Irradiationmentioning

confidence: 99%

Section: Mw Irradiationmentioning

confidence: 99%

Solvent‐Free and Catalysts‐Free Chemistry: A Benign Pathway to Sustainability

Gawande¹,

Bonifácio²,

Luque³

et al. 2013

ChemSusChem

278

122

View full text Add to dashboard Cite

show abstract

“…Many catalytic systems have been performed for the synthesis of DHPMs through the Biginelli reaction, including Lewis acid, BrØnsted acid, and organic bases such as L ‐tyrosine, Phatic acid, PPh 3 , β ‐Cyclodextrin, L ‐proline derivatives, Cobalt (II)‐phthalocyanine, Li (glycine)(CF 3 SO 3 ), TiO 2 ‐MWCNTs, Ionic liquid, SiO 2 ‐CuCl 2 , ZAF‐16 and PPF‐SO 3 H . Additionally, some other techniques for the synthesis of DHPMs have also been employed in the Biginelli condensation reaction, for instance, ionic liquid, solvent‐free, solid‐state synthesis, ultrasound and microwave . Recently, IRMOF‐3 and Cd‐based MCCs were successfully employed in the synthesis of DHPMs with good yields .…”

Section: Introductionmentioning

confidence: 99%

A Set of phenyl sulfonate metal coordination complexes triggered Biginelli reaction for the high efficient synthesis of 3,4‐dihydropyrimidin‐2(1H)‐ones under solvent‐free conditions

Wang

Tang

2020

Applied Organom Chemis

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Three new metal coordination complexes, namely, [Co (DPE)(H2O)4](DPE)(BS)2 (1), [Co (DPE)2(H2O)4](ABS)2 (2), [Co (DPE)(H2O)4](MBS)2(CH3OH)2 (3) [DPE = (E)‐1,2‐di (pyridin‐4‐yl) ethene, BS = phenyl sulfonic acid, ABS = p‐aminobenzene sulfonic acid, MBS = p‐methylbenzene sulfonic acid] were obtained under hydrothermal conditions. Complexes 1‐3 were structurally characterized by X‐ray single‐crystal diffraction, powder X‐ray diffraction and IR. Complexes 1 and 3 exhibit a one‐dimensional chain structure, and complex 2 does a zero‐dimensional one. These three complexes further generate a three‐dimensional supramolecular architecture via strong hydrogen bonding interactions and packing interactions. These three metal coordination complexes show high catalytic performance for green synthesis of a variety of 3,4‐dihydropyrimidin‐2(1H)‐ones through the Biginelli reactions, which show several advantages such as excellent yields, short reaction times, eco‐friendly synthesis conditions, and simple isolated workup procedure. Interestingly, the order of catalytic activities for these catalysts is the following: 3>1>2, which can be ascribed to the acidities and hydrophobic interactions of phenyl sulfonate groups.

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“…Several literature reviews highlight the magnificence of research. [ 28–33 ] Some other reviews focus on relatively specific topics, including nucleophilic dearomatization, [ 34 ] transition‐metal‐mediated dearomatization reactions, [ 35 ] dearomatization in presence of chiral phosphoric acid, [ 36 ] dearomatization through halofunctionalization reactions, [ 37 ] multicomponent reactions in polymer chemistry, [ 38 ] metal‐catalyzed multicomponent reactions, [ 39 ] synthesis of tetrazoles via multicomponent reactions [ 40 ] and the recent developments in the synthesis of pyrido[1,2‐ a ]benzimidazoles. [ 41 ] Reviews on recent progress in multicomponent reactions of pyrimidine synthesis [ 42 ] or recent developments in the synthesis of imidazo[1,2‐ a ]pyridines have also been reported.…”

Section: Introductionmentioning

confidence: 99%

Cyclative MCRs of Azines and Azinium Salts

et al. 2020

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Since the first discovery by Huigsen and co-workers fifty years ago, a wide range of organic reactions have taken place through the intermediary of the dipolar/zwitterionic species produced by the combination of a neutral nucleophile and an unsaturated electrophile. Nucleophilic initiators including heterocycles may react or play a mediating role based on their nucleophilic nature and reaction conditions. This review highlights the recent developments of the cyclization chemistry of [a] A

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A microwave-mediated catalyst- and solvent-free regioselective Biginelli reaction in the synthesis of highly functionalized novel tetrahydropyrimidines

Cited by 36 publications

References 40 publications

Solvent‐Free and Catalysts‐Free Chemistry: A Benign Pathway to Sustainability

Solvent‐Free and Catalysts‐Free Chemistry: A Benign Pathway to Sustainability

A Set of phenyl sulfonate metal coordination complexes triggered Biginelli reaction for the high efficient synthesis of 3,4‐dihydropyrimidin‐2(1H)‐ones under solvent‐free conditions

Cyclative MCRs of Azines and Azinium Salts

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