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Journal articles on the topic 'Biginelli reactions'

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Published: 10 March 2023

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1

Heravi, Majid M., and Vahideh Zadsirjan. "Recent Advances in Biginelli-type Reactions." Current Organic Chemistry 24, no. 12 (September 22, 2020): 1331–66. http://dx.doi.org/10.2174/1385272824999200616111228.

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The effective and high yielding synthesis of poly-functionalized pyrimidines, using multicomponent reactions (MCRs), is imperative in organic and medicinal chemistry. The classic Biginelli reaction is a typically one-pot three-component cyclocondensation reaction involving an aldehyde, a β-ketoester and urea, resulting in the construction of multi-functionalized 3,4-dihydropyrimidin-2(1H)-ones (DHPMs). In recent years, other active methylene compounds, various derivatives of urea and diversely substituted aldehydes have also been used, resulting in the preparation of a new series of various novel dihydropyrimidinones via the Biginelli-Type Reactions (BTRs) or modified Biginelli reactions (MBRs). In this review, we try to underscore the recent advances in BTRs or MBRs.
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2

Ma, Zeyu, Bo Wang, and Lei Tao. "Stepping Further from Coupling Tools: Development of Functional Polymers via the Biginelli Reaction." Molecules 27, no. 22 (November 15, 2022): 7886. http://dx.doi.org/10.3390/molecules27227886.

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Multicomponent reactions (MCRs) have been used to prepare polymers with appealing functions. The Biginelli reaction, one of the oldest and most famous MCRs, has sparked new scientific discoveries in polymer chemistry since 2013. Recent years have seen the Biginelli reaction stepping further from simple coupling tools; for example, the functions of the Biginelli product 3,4-dihydropyrimidin-2(1H)-(thi)ones (DHPM(T)) have been gradually exploited to develop new functional polymers. In this mini-review, we mainly summarize the recent progress of using the Biginelli reaction to identify polymers for biomedical applications. These polymers have been documented as antioxidants, anticancer agents, and bio-imaging probes. Moreover, we also provide a brief introduction to some emerging applications of the Biginelli reaction in materials and polymer science. Finally, we present our perspectives for the further development of the Biginelli reaction in polymer chemistry.
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3

Tahmasbi, Marzieh, Nadiya Koukabi, and Ozra Armandpour. "Sono and nano: A perfect synergy for eco-compatible Biginelli reaction." Heterocyclic Communications 28, no. 1 (January 1, 2022): 1–10. http://dx.doi.org/10.1515/hc-2022-0003.

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Abstract In this study, we evaluated the performance of nano-γ-Fe2O3–SO3H catalyst in the Biginelli reaction and synthesized 3,4-dihydropyrimidine-2-(1H)-ones. This reaction was carried out under solvent-free and ultrasonic irradiation conditions and belonged to one-pot multicomponent reactions (MCRs) with an adopted aromatic aldehyde, ethyl acetoacetate, and urea as starting materials for the beginning of the reaction. The synthesized materials were efficient in synthesizing 3,4-dihydropyrimidine-2-(1H)-ones via the Biginelli reaction under reaction conditions. Thus, the advantages of using nano-γ-Fe2O3–SO3H in the Biginelli reaction are short reaction time, high efficiency, green method, solvent free, and cost-effective. Furthermore, nano-γ-Fe2O3–SO3H as a heterogeneous catalyst can be recycled five times without significantly reducing catalytic activity.
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4

Krishna, Thalishetti, Eppakayala Laxminarayana, and Dipak Kalita. "FeF3 as a green catalyst for the synthesis of dihydropyrimidines via Biginelli reaction." European Journal of Chemistry 11, no. 3 (September 30, 2020): 206–12. http://dx.doi.org/10.5155/eurjchem.11.3.206-212.1992.

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A facile and highly efficient FeF3-catalyzed method has been developed for the direct synthesis of functionalized dihydropyrimidines from readily available starting materials via Biginelli reaction. These reactions proceed at low-catalyst loadings with high functional group tolerance under mild conditions. This method provides efficient reusability of the catalyst and good to excellent yields of the products, making the protocol more attractive, economical, and environmentally benign. FeF3 is an attractive catalyst for the Biginelli reaction because of its high acidity, thermal stability and water tolerance.
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5

Safari, Javad, Soheila Gandomi-Ravandi, and Samira Ashiri. "Organosilane sulfonated graphene oxide in the Biginelli and Biginelli-like reactions." New Journal of Chemistry 40, no. 1 (2016): 512–20. http://dx.doi.org/10.1039/c5nj01741f.

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6

Sánchez-Sancho, Francisco, Marcos Escolano, Daniel Gaviña, Aurelio G. Csáky, María Sánchez-Roselló, Santiago Díaz-Oltra, and Carlos del Pozo. "Synthesis of 3,4-Dihydropyrimidin(thio)one Containing Scaffold: Biginelli-like Reactions." Pharmaceuticals 15, no. 8 (July 30, 2022): 948. http://dx.doi.org/10.3390/ph15080948.

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The interest in 3,4-dihydropyrimidine-2(1H)-(thio)ones is increasing every day, mainly due to their paramount biological relevance. The Biginelli reaction is the classical approach to reaching these scaffolds, although the product diversity suffers from some limitations. In order to overcome these restrictions, two main approaches have been devised. The first one involves the modification of the conventional components of the Biginelli reaction and the second one refers to the postmodification of the Biginelli products. Both strategies have been extensively revised in this manuscript. Regarding the first one, initially, the modification of one of the components was covered. Although examples of modifications of the three of them were described, by far the modification of the keto ester counterpart was the most popular approach, and a wide variety of different enolizable carbonylic compounds were used; moreover, changes in two or the three components were also described, broadening the substitution of the final dihydropyrimidines. Together with these modifications, the use of Biginelli adducts as a starting point for further modification was also a very useful strategy to decorate the final heterocyclic structure.
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7

Boukis, Andreas C., Baptiste Monney, and Michael A. R. Meier. "Synthesis of structurally diverse 3,4-dihydropyrimidin-2(1H)-ones via sequential Biginelli and Passerini reactions." Beilstein Journal of Organic Chemistry 13 (January 9, 2017): 54–62. http://dx.doi.org/10.3762/bjoc.13.7.

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The Biginelli reaction was combined with the Passerini reaction for the first time in a sequential multicomponent tandem reaction approach. After evaluation of all possible linker components and a suitable solvent system, highly functionalized dihydropyrimidone–α-acyloxycarboxamide compounds were obtained in good to excellent yields. In a first reaction step, different 3,4-dihydropyrimidin-2(1H)-one acids were synthesized, isolated and fully characterized. These products were subsequently used in a Passerini reaction utilizing a dichloromethane/dimethyl sulfoxide solvent mixture. By variation of the components in both multicomponent reactions, a large number of structurally diverse compounds could be synthesized. In addition, a one-pot Biginelli–Passerini tandem reaction was demonstrated. All products were carefully characterized via 1D and 2D NMR as well as IR and HRMS.
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8

Hu, Xiaoyun, Jianxin Guo, Cui Wang, Rui Zhang, and Victor Borovkov. "Stereoselective Biginelli-like reaction catalyzed by a chiral phosphoric acid bearing two hydroxy groups." Beilstein Journal of Organic Chemistry 16 (July 31, 2020): 1875–80. http://dx.doi.org/10.3762/bjoc.16.155.

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To develop new efficient stereoselective catalysts for Biginelli-like reactions, a chiral phosphoric acid bearing two hydroxy groups derived from ʟ-tartaric acid was successfully synthesized via highly regioselective transformations of enantiopure 1,1,4,4-tetraphenylbutanetetraol. The obtained catalyst effectively catalyzed Biginelli-like reactions with moderate to good enantioselectivities. Control experiments indicated that the presence of the two hydroxy groups were indispensable for achieving a high enantioselectivity.
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9

Khaskel, Anamika, Pranjit Barman, Subir Kumar Maiti, and Utpal Jana. "Nebivolol nanoparticles: a first catalytic use in Biginelli and Biginelli-like reactions." Canadian Journal of Chemistry 96, no. 12 (December 2018): 1021–25. http://dx.doi.org/10.1139/cjc-2017-0621.

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Herein, we report the catalytic activity of nebivolol nanoparticles a novel organocatalyst for the synthesis of DHPMs and DHPM-5-carboxamides. The nanoparticles are confirmed by DSC, TEM, AFM, and IR spectroscopy. The catalyst can be readily recovered and reused for the next four runs without any significant impact on the yields of the products. The products are fully characterized by FTIR, 1H NMR, 13C NMR, and distortionless enhanced polarization transfer (DEPT) NMR. The methodology adopted here offers several advantages such as solvent-free reaction, low loading of catalyst, short reaction times, and quantifiable yields.
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10

Dallinger, Doris, A. Stadler, and C. O. Kappe. "Solid- and solution-phase synthesis of bioactive dihydropyrimidines." Pure and Applied Chemistry 76, no. 5 (January 1, 2004): 1017–24. http://dx.doi.org/10.1351/pac200476051017.

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With the emergence of high-throughput screening in the pharmaceutical industry over a decade ago, synthetic chemists were faced with the challenge of preparing large collections of molecules to satisfy the demand for new screening compounds. The unique exploratory power of multicomponent reactions such as the Biginelli three-component reaction was soon recognized to be extremely valuable to produce compound libraries in a time- and cost-effective manner. The present review summarizes synthetic advances from our laboratories for the construction of Biginelli libraries via solution-and solid-phase strategies that are amenable to a high-throughput or combinatorial format.
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11

Luo, Zhi Chen. "Nanostructural Zinc Oxide Hollow Spheres Catalyzed Synthesis of 3, 4-Dihydropyrimidin-2(1H)-Ones under Solvent-Free Conditions." Advanced Materials Research 233-235 (May 2011): 273–76. http://dx.doi.org/10.4028/www.scientific.net/amr.233-235.273.

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A simple synthesis of 3,4-dihydropyrimidinones from the aldehyde, 1,3-dicarbonyl compound, and urea (thiourea) using nanostructural zinc oxide hollow spheres as the catalyst under solvent-free conditions is described. Compared with traditional Biginelli reactions, this method has advantages of excellent yields and short reaction time.
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12

Xu, Li-Wen, Ming-Song Yang, Jian-Xiong Jiang, Hua-Yu Qiu, and Guo-Qiao Lai. "Ionic liquid-functionalized SBA-15 mesoporous material: efficient heterogeneous catalyst in versatile organic reactions." Open Chemistry 5, no. 4 (December 1, 2007): 1073–83. http://dx.doi.org/10.2478/s11532-007-0044-6.

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AbstractIonic liquid-functionalized mesoporous materials exhibited high catalytic activity in versatile organic reactions, such as cycloaddition of carbon dioxide (CO2) with epoxide, aza-Michael addition of amines to α, β-unsaturated carbonyl compounds, and the Biginelli reaction of aldehyde, ethyl acetoacetate and urea. Recycling of the catalyst in these reactions could be carried out and the catalyst used at least five times without significant loss in activity.
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13

Suzuki, Ichiro, Yukari Iwata, and Kei Takeda. "Biginelli reactions catalyzed by hydrazine type organocatalyst." Tetrahedron Letters 49, no. 20 (May 2008): 3238–41. http://dx.doi.org/10.1016/j.tetlet.2008.03.080.

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14

Ryabukhin, Sergey V., Andrey S. Plaskon, Sergey Yu Boron, Dmitriy M. Volochnyuk, and Andrey A. Tolmachev. "Aminoheterocycles as synthons for combinatorial Biginelli reactions." Molecular Diversity 15, no. 1 (May 7, 2010): 189–95. http://dx.doi.org/10.1007/s11030-010-9253-6.

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15

Fan, Weigang, Yves Queneau, and Florence Popowycz. "HMF in multicomponent reactions: utilization of 5-hydroxymethylfurfural (HMF) in the Biginelli reaction." Green Chemistry 20, no. 2 (2018): 485–92. http://dx.doi.org/10.1039/c7gc03425c.

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16

Hamlin, Trevor A., and Nicholas E. Leadbeater. "Raman spectroscopy as a tool for monitoring mesoscale continuous-flow organic synthesis: Equipment interface and assessment in four medicinally-relevant reactions." Beilstein Journal of Organic Chemistry 9 (September 11, 2013): 1843–52. http://dx.doi.org/10.3762/bjoc.9.215.

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An apparatus is reported for real-time Raman monitoring of reactions performed using continuous-flow processing. Its capability is assessed by studying four reactions, all involving formation of products bearing α,β-unsaturated carbonyl moieties; synthesis of 3-acetylcoumarin, Knoevenagel and Claisen–Schmidt condensations, and a Biginelli reaction. In each case it is possible to monitor the reactions and also in one case, by means of a calibration curve, determine product conversion from Raman spectral data as corroborated by data obtained using NMR spectroscopy.
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17

Patil, Vishvanath D., Amruta M. Salve, V. D. Gharat, and N. Gawand. "Multicomponent one pot synthesis of Substituted 3,4-Dihydropyrimidin-2-(1H)-ones by Nanocrystalline CeO2." Research Journal of Chemistry and Environment 25, no. 8 (July 25, 2022): 83–89. http://dx.doi.org/10.25303/258rjce8389.

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One of the most prominent multicomponent reactions (MCRs), Biginelli reaction has been utilized for the synthesis of 3,4-dihydropyrimidin-2-(1H)-ones catalyzed one-pot condensation of aldehyde, β- ketoester and urea in presence of ethanol. The present study deals with synthesis of biologically active 3, 4- dihydropyrimidin-2(1H)-ones using nano crystalline CeO2.
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18

Bosica, Giovanna, Fiona Cachia, Riccardo De Nittis, and Nicole Mariotti. "Efficient One-Pot Synthesis of 3,4-Dihydropyrimidin-2(1H)-ones via a Three-Component Biginelli Reaction." Molecules 26, no. 12 (June 20, 2021): 3753. http://dx.doi.org/10.3390/molecules26123753.

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Multicomponent reactions are considered to be of increasing importance as time progresses due to the economic and environmental advantages such strategies entail. The three-component Biginelli reaction involves the combination of an aldehyde, a β-ketoester and urea to produce 3,4-dihydropyrimidin-2(1H)-ones, also known as DHPMs. The synthesis of these products is highly important due to their myriad of medicinal properties, amongst them acting as calcium channel blockers and antihypertensive and anti-inflammatory agents. In this study, silicotungstic acid supported on Ambelyst-15 was used as a heterogeneous catalyst for the Biginelli reaction under solventless conditions. Electron-poor aromatic aldehydes gave the best results. Sterically hindered β-ketoesters resulted in lower reaction yields. The reaction was carried out under heterogeneous catalysis to allow easy recovery of the product from the reaction mixture and recycling of the catalyst. The heterogeneity of the reaction was confirmed by carrying out a hot filtration test.
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19

Guggilapu, Sravanthi Devi, Santosh Kumar Prajapti, Atulya Nagarsenkar, Guntuku Lalita, Ganga Modi Naidu Vegi, and Bathini Nagendra Babu. "MoO2Cl2 catalyzed efficient synthesis of functionalized 3,4-dihydropyrimidin-2(1H)-ones/thiones and polyhydroquinolines: recyclability, fluorescence and biological studies." New Journal of Chemistry 40, no. 1 (2016): 838–43. http://dx.doi.org/10.1039/c5nj02444g.

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20

Felluga, Fulvia, Fabio Benedetti, Federico Berti, Sara Drioli, and Giorgia Regini. "Efficient Biginelli Synthesis of 2-Aminodihydropyrimidines under Microwave Irradiation." Synlett 29, no. 08 (January 31, 2018): 1047–54. http://dx.doi.org/10.1055/s-0036-1591900.

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A practical and general method for the Biginelli cyclocondensation of guanidine with aldehydes and β-dicarbonyl compounds is described and illustrated with the synthesis of a set of 26 functionalized 2-amino-3,4-dihydropyrimidines. The simple protocol involves the ­microwave-mediated reaction of a twofold excess of guanidine hydrochloride with the required reaction partners in an alcohol at 120 °C. Yields are generally good, with short reaction times and a simple workup. The scope is considerably wider than that of similar reactions ­carried out under conventional heating.
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21

Noppawan, Pakin, Suwiwat Sangon, Nontipa Supanchaiyamat, and Andrew J. Hunt. "Vegetable oil as a highly effective 100% bio-based alternative solvent for the one-pot multicomponent Biginelli reaction." Green Chemistry 23, no. 16 (2021): 5766–74. http://dx.doi.org/10.1039/d1gc00872b.

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22

Zhang, Qiguo, Xin Wang, Zhenjiang Li, Wenzhuo Wu, Jingjing Liu, Hao Wu, Saide Cui, and Kai Guo. "Phytic acid: a biogenic organocatalyst for one-pot Biginelli reactions to 3,4-dihydropyrimidin-2(1H)-ones/thiones." RSC Adv. 4, no. 38 (2014): 19710–15. http://dx.doi.org/10.1039/c4ra02084g.

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23

Kappe, Christian Oliver, and Peter Roschger. "Synthesis and reactions of “biginelli-compounds”. Part I." Journal of Heterocyclic Chemistry 26, no. 1 (January 1989): 55–64. http://dx.doi.org/10.1002/jhet.5570260112.

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24

Timoshenko, Vadim M., Yuriy M. Markitanov, and Yuriy G. Shermolovich. "2-Oxo-2-polyfluoroalkylethane-1-sulfones and -sulfamides in the Biginelli and ‘retro-Biginelli’ reactions." Tetrahedron Letters 52, no. 49 (December 2011): 6619–22. http://dx.doi.org/10.1016/j.tetlet.2011.09.143.

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25

Piqani, Bruno, and Wei Zhang. "Synthesis of diverse dihydropyrimidine-related scaffolds by fluorous benzaldehyde-based Biginelli reaction and post-condensation modifications." Beilstein Journal of Organic Chemistry 7 (September 16, 2011): 1294–98. http://dx.doi.org/10.3762/bjoc.7.150.

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Dihydropyrimidinones and dihydropyrimidinethiones generated from the Biginelli reactions of perfluorooctanesulfonyl-attached benzaldehydes are used as common intermediates for post-condensation modifications such as cycloaddition, Liebeskind–Srogl reaction and Suzuki coupling to form biaryl-substituted dihydropyrimidinone, dihydropyrimidine, and thiazolopyrimidine compounds. The high efficiency of the diversity-oriented synthesis is achieved by conducting a multicomponent reaction for improved atom economy, under microwave heating for fast reaction, and with fluorous solid-phase extractions (F-SPE) for ease of purification.
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26

Raj, Tilak, Beant Kaur Billing, Navneet Kaur, and Narinder Singh. "Design, synthesis and antimicrobial evaluation of dihydropyrimidone based organic–inorganic nano-hybrids." RSC Advances 5, no. 58 (2015): 46654–61. http://dx.doi.org/10.1039/c5ra08765a.

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Substituted dihydropyrimidone derivatives were synthesized through one pot multicomponent Zn(ClO4)2catalysed Biginelli reactions between differently substituted aromatic aldehydes, urea and ethylacetoacetate.
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27

Wang, Jin-Hua, Gui-Mei Tang, Yong-Tao Wang, Yue-Zhi Cui, Jun-Jie Wang, and Seik Weng Ng. "A series of phenyl sulfonate metal coordination polymers as catalysts for one-pot Biginelli reactions under solvent-free conditions." Dalton Transactions 44, no. 40 (2015): 17829–40. http://dx.doi.org/10.1039/c5dt03135d.

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A series of phenyl sulfonate metal coordination polymers have been obtained under hydrothermal conditions, which show high catalytic performances for one-pot Biginelli condensation reactions under solvent-free conditions.
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28

Gupta, Anoop K., Dinesh De, Kapil Tomar, and Parimal K. Bharadwaj. "A Cu(ii) metal–organic framework with significant H2 and CO2 storage capacity and heterogeneous catalysis for the aerobic oxidative amination of C(sp3)–H bonds and Biginelli reactions." Dalton Transactions 47, no. 5 (2018): 1624–34. http://dx.doi.org/10.1039/c7dt04006g.

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29

Kapoor, Kamal K., Bilal A. Ganai, Satish Kumar, and Charanjeet S. Andotra. "Antimony(III) chloride impregnated on alumina — An efficient and economical Lewis acid catalyst for one-pot synthesis of dihydropyrimidinones under solvent-free conditions." Canadian Journal of Chemistry 84, no. 3 (March 1, 2006): 433–37. http://dx.doi.org/10.1139/v06-019.

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The antimony(III) chloride impregnated on alumina efficiently catalyses a one-pot, three-component condensation reaction among an aldehyde, a β-ketoester, and urea or thiourea to afford the corresponding dihydropyrimidinones in good to excellent yields. The reactions are probed in microwave (MW), ultrasonic, and thermal conditions and the best results are found using MW under solvent-free conditions.Key words: Biginelli dihydropyrimidinones synthesis, SbCl3–Al2O3, MW, sonication, solid supported.
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30

Liu, Zong-liang, Ren-mei Zhang, Ye Liu, Yan Guo, and Qing-guo Meng. "The Effects of Different Catalysts, Substituted Aromatic Aldehydes on One-Pot Three-Component Biginelli Reaction." Current Organic Synthesis 16, no. 1 (February 4, 2019): 181–86. http://dx.doi.org/10.2174/1570179416666181122100405.

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Aim and Objective: The Biginelli reaction, first reported in 1893, is one great example of the important multicomponent reactions reported from 1893. Under the same conditions, the influence of the common catalysts on the yield of the Biginelli reaction was investigated. </P><P> Materials and Method: To a round-bottom flask equipped with a spherical condenser were added 1,3- dicarbonyl compound (1.0 eq), urea (1.45 eq), aromatic aldehyde (1.0 eq), catalyst and methanol. The mixture was heated at reflux for 16 h. After cooling off, the mixture was filtered and washed with cold methanol to give DHPMs. Reaction solution was further purified by recrystallization with petroleum ether and ethyl acetate. Six catalytic systems, different 1,3-dicarbonyl compounds and different substituted aromatic aldehydes with varied substitutions are described for the Biginelli reaction. An analysis was also performed to study the factors that affect the yield of the reaction. </P><P> Results: When 1,3-dicarbonyl compound was ethyl acetoacetate, the CuCl/ conc.H2SO4 system gave the highest yield (90.5%). While when acetoacetamide was used, the yields of DHPMs in presence of PTSA/conc. HCl, conc. HCl or FeCl3•6H2O were all over 90%. Nine DHPMs with different substituents were obtained. Conclusion: The Lewis acid or mixed catalyst had no significant advantage over a single protonic acid as catalyst. Conc. HCl as the catalyst was found to be the most effective condition for the preparation of DHPMs. The aromatic aldehyde with weak electron-withdrawing substituent such as Br resulted in the best yield.
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31

Ghafoor, Abdul, Naveed Sajid, Asma Mukhtar, Shahid Ali, Samina Aslam, Mahrzadi Noureen Shahi, Muhammad Adnan, and Misbahul Ain Khan. "Phenols Catalyzed Biginelli Reactions: A Self Catalyzed Monastrol Protocol." Asian Journal of Chemistry 28, no. 1 (2016): 23–26. http://dx.doi.org/10.14233/ajchem.2016.19156.

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32

Wu, Haibo, Changkui Fu, Yuan Zhao, Bin Yang, Yen Wei, Zhiming Wang, and Lei Tao. "Multicomponent Copolycondensates via the Simultaneous Hantzsch and Biginelli Reactions." ACS Macro Letters 4, no. 11 (October 15, 2015): 1189–93. http://dx.doi.org/10.1021/acsmacrolett.5b00637.

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33

Khademinia, Shahin, Mahdi Behzad, Abdolali Alemi, Mahboubeh Dolatyari, and S. Maryam Sajjadi. "Catalytic performance of bismuth pyromanganate nanocatalyst for Biginelli reactions." RSC Advances 5, no. 87 (2015): 71109–14. http://dx.doi.org/10.1039/c5ra11432b.

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34

Dương, Công-Thắng, and Xuan Thi Thi Luu. "The ultrasound accelerated solvent-free synthesis of ethyl 7-methyl-5-phenyl-5H-thiazolo[3,2-a]pyrimidine-6-carboxylate through Biginelli reaction catalyzed by Amberlyst-15." Science and Technology Development Journal - Natural Sciences 4, no. 3 (August 24, 2020): First. http://dx.doi.org/10.32508/stdjns.v4i3.868.

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Multi-component reactions (MCRs) played an important role to produce complex molecular structures in a one-step process. Among all MCRs reported, Biginelli reaction was one of the most well-known and used in organic synthesis to constitute pyrimidine scaffolds. Therefore, a solvent-free Biginelli reaction of 2-aminothiazole, benzaldehyde and ethyl acetoacetate catalyzed by Amberlyst-15 (A-15) had attracted us to pay attention and to do research in order to highly obtain a desired product, a frame of thiazolo[3,2-a]pyrimidine being present in many active biological compounds. Amberlyst-15, polystyrene resin regarded as a green acidic solid, available commercial, inexpensive and reusable catalyst had been firstly and successfully developed for solvent-free Biginelli reaction under ultrasound irradiation to form thiazolo[3,2-a]pyrimidine. Most factors which had influenced on the reaction conversion and yield such as the molar ratios between 2-aminothiazole, benzaldehyde and ethyl acetoacetate, the amounts of catalyst A-15, and reaction time had been investigated. Consequently, the yield of ethyl 7-methyl-5-phenyl-5H-thiazolo[3,2-a]pyrimidine-6-carboxylate had been also found to depend on the amount of the acidic solid catalyst and little excess amounts of the two reactants, e.g. 2-aminothiazole and ethyl acetoacetate. The maximum yield has been obtained 76% after six-hour ultrasound irradiation at 80oC with the molar ratio of 2-aminothiazole : benzaldehyde : ethyl acetoacetate (1.4:1.0:1.4) and 50 mg of catalyst A-15. The results showed that Amberlyst-15 had high capability of recovery and recycling owing to the inconsiderably changes of product yields after two recycle runs.
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35

Mansano Willig, Julia C., Gustavo Granetto, Danielly Reginato, Felipe R. Dutra, Érica Fernanda Poruczinski, Isadora M. de Oliveira, Helio A. Stefani, et al. "A comparative study between Cu(INA)2-MOF and [Cu(INA)2(H2O)4] complex for a click reaction and the Biginelli reaction under solvent-free conditions." RSC Advances 10, no. 6 (2020): 3407–15. http://dx.doi.org/10.1039/c9ra10171c.

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The catalytic application of Cu(INA)2-MOF in click and Biginelli reactions was investigated and a comparative study with the [Cu(INA)2(H2O)4] complex was performed.
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36

Gülten, Şirin, Ufuk Gezer, and Elmas Aksanli Gündoğan. "Fast and Efficient One-Pot Three-Component Synthesis of Some 1,2,3,4- Tetrahydro-6-methyl-N-phenyl-5-pyrimidinecarboxamide Derivatives via Biginelli Condensation Reaction." Letters in Organic Chemistry 17, no. 5 (April 28, 2020): 366–71. http://dx.doi.org/10.2174/1570178616666190819142221.

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Tetrahydropyrimidine (THPM) synthesis has an enormous importance in organic chemistry and especially in pharmaceutical applications. Pyrimidines are the most active class of N-containing heterocyclic compounds and have different biological properties. The heterocyclic ring system with a thio group occupy a unique position in medicinal chemistry. This type of compounds play an important role in synthetic drugs and in biological processes. Dihydropyrimidinethione derivatives occur widely in nature. Several modifications of THPM-5-carboxamides have attracted considerable interest of medicinal chemists due to their pharmacological and therapeutic properties. A series of 1,2,3,4-tetrahydro- 2-pyrimidinone/thione derivatives bearing a phenylcarbamoyl group at C-5 position were synthesized by one-pot three-component Biginelli condensation reaction. The reaction of acetoacetanilide as the 1,3-dicarbonyl component with various aromatic aldehydes and urea/thiourea in the presence of a catalytic amount of p-toluenesulfonic acid monohydrate (PTSA·H2O) or concentrated HCl as an efficient catalyst leads to Biginelli compounds. We have prepared eight THPM 5-carboxamide derivatives, four of them are new compounds. Their structures were confirmed by spectroscopic techniques and elemental analysis. These compounds have potential applications in organic synthesis and medicinal chemistry. We have synthesized a series of THPM-5-carboxamides by simple and efficient threecomponent Biginelli condensation reaction. Significant benefits of the present procedure include: a) application of inexpensive, non-toxic, environmentally friendly and easily available catalysts, b) the reactions are easy to carry out without high temperature and the workup is very simple, c) the required reaction times are relatively short (30-80 min with HCl and 8-24 h with PTSA·H2O), d) compatibility with various functional groups, e) the products are isolated in good to excellent yields (50-95%).
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37

Gulati, Shivani, Stephy Elza John, and Nagula Shankaraiah. "Microwave-assisted multicomponent reactions in heterocyclic chemistry and mechanistic aspects." Beilstein Journal of Organic Chemistry 17 (April 19, 2021): 819–65. http://dx.doi.org/10.3762/bjoc.17.71.

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Microwave-assisted (MWA) multicomponent reactions (MCRs) have successfully emerged as one of the useful tools in the synthesis of biologically relevant heterocycles. These reactions are strategically employed for the generation of a variety of heterocycles along with multiple point diversifications. Over the last few decades classical MCRs such as Ugi, Biginelli, etc. have witnessed enhanced yield and efficiency with microwave assistance. The highlights of MWA-MCRs are high yields, reduced reaction time, selectivity, atom economy and simpler purification techniques, such an approach can accelerate the drug discovery process. The present review focuses on the recent advances in MWA-MCRs and their mechanistic insights over the past decade and shed light on its advantage over the conventional approach.
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38

Shaikh, Tanveer M., Sankaranarayanan Nagarajan, and Elango Kandasamy. "One Pot Multicomponent Biginelli Reaction Employing Ionic Liquids as an Organocatalyst." Current Organocatalysis 7, no. 2 (July 2, 2020): 96–107. http://dx.doi.org/10.2174/2213337206666191001214521.

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Introduction: The N-heterocyclic compounds have been extensively studied in pharmaceutical industries. Furthermore, syntheses of such compounds employing organo-catalyst have been associated with sustainable technology. Methods: The synthesis of new, stable ionic liquids and their catalytic applications in one-pot multicomponent Biginelli reaction is presented. The method provides broad substrate scope, yielding the corresponding 3,4-dihydropyrimidin-2(1H)-ones and 3,4-dihydropyrimidin-2(1H)-thiones, in good to excellent yields, respectively. Results and Conclusion: The developed reactions are associated with certain advantages, short reaction time and sustainable conditions. The protocol has advantages eco-friendly procedure, recovery and reusability of catalyst, which showed consistent activity.
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39

Díaz-Fernández, Marcos, Saturnino Calvo-Losada, J. Joaquín Quirante, Francisco Sarabia, Manuel Algarra, and M. Soledad Pino-González. "Catalyzed Methods to Synthesize Pyrimidine and Related Heterocyclic Compounds." Catalysts 13, no. 1 (January 12, 2023): 180. http://dx.doi.org/10.3390/catal13010180.

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This review covers articles published in the period from 2010 to mid-2022 on synthetic advances in the formation of pyrimidine and related heterocyclic compounds. Special emphasis has been given to the different types of cycloadditions, taking into account the number of their components and leading to the formation of the pyrimidine ring. Due to the large number of publications on the Biginelli reaction and related reactions, this will be dealt with in a separate review in the near future.
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Manhas, Maghar S., Subhendu N. Ganguly, Somdatta Mukherjee, Amit K. Jain, and Ajay K. Bose. "Microwave initiated reactions: Pechmann coumarin synthesis, Biginelli reaction, and acylation." Tetrahedron Letters 47, no. 14 (April 2006): 2423–25. http://dx.doi.org/10.1016/j.tetlet.2006.01.147.

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41

Changmai, Bishwajit, Kalyani Rajkumari, Diparjun Das, and Lalthazuala Rokhum. "Microwave-assisted Synthesis of 3,4-Dihydropyrimidin-2(1H)-ones Using Acid-Functionalized Mesoporous Polymer." Current Microwave Chemistry 8, no. 1 (July 13, 2021): 44–53. http://dx.doi.org/10.2174/2213335608666210329130736.

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Background: In recent years, 3,4-dihydro-pyrimidin-2-(1H)-ones (DHPMs) have attracted significant attention due to their diverse range of biological properties such as antibacterial, antiviral, antitumor, anti-inflammatory, calcium channel blocking activities, etc. Taking into account, in this present work, a polymer-based solid acid catalyst is employed for the microwaveassisted synthesis of DHPMs. Introduction: Multicomponent reactions (MCRs) are attracting utmost attention as they promote the formation of several bonds in a single process with diverse advantages. Biginelli reaction is the top-ranked example of MCR for the synthesis of dihydropyrimidinones (DHPMs). Solid catalysts are considered a significant tool for MCRs as they are non-toxic, easy to handle, reusable, and have high selectivity and easy separation process. Methods: DHPMs synthesis was carried out using acid-functionalized mesoporous polymer (AFMP) catalyst under microwave irradiation and solvent-free condition. Results: AFMP showed good to excellent DHPMs yield (89-98%) under the optimized reaction conditions: 1:1:1.2 molar ratio of aldehyde/ethyl acetoacetate/urea, catalyst loading of 6 wt.% (with respect to aldehyde), the temperature of 80 °C and microwave power of 500 W. Conclusion: We have successfully utilized microwave-assisted AFMP catalyst for the synthesis of DHPMs under solvent-free conditions via the Biginelli approach. The catalyst is recyclable and reusable in up to 5 consecutive reaction cycles with no significant loss in catalytic activity.
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42

Bhuiyan, M. H., H. Nessa, and M. M. Mahmud. "Multicomponent Reactions: Microwave-assisted Efficient Synthesis of Dihydropyrimidinones (thiones) and Quinazolinones under Green Chemistry Protocol as Probes for Antimicrobial Activities." Journal of Scientific Research 4, no. 1 (December 26, 2011): 143. http://dx.doi.org/10.3329/jsr.v4i1.8688.

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Microwave promoted diammonium hydrogen phosphate, (NH4)2HPO4, catalyzed three-component Biginelli reaction between an aldehyde, a 1,3-dicarbonyl compound and urea or thiourea under solvent-free conditions afforded the corresponding dihydropyrimidinones and quinazolinones in high yields. The synthesized compounds have been screened for their antimicrobial activity against Pseudomonas aeruginosa, Staphylococcus aureus, Vibrio choloriae, Shigella dysenteriae, Salmonella typhi bacteria and Aspargilllus flavus, Saccharomyces cerevisiae and Candida albicans fungi respectively. Some of the synthesized compounds exhibited pronounced antimicrobial activities.Keywords: Multicomponent reactions; Dihydropyrimidinone; Microwave irradiation; Antimicrobial activity.© 2012 JSR Publications. ISSN: 2070-0237 (Print); 2070-0245 (Online). All rights reserved.doi: http://dx.doi.org/10.3329/jsr.v4i1.8688J. Sci. Res. 4 (1), 143-153 (2012)
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43

Saloutin, V. I., Ya V. Burgart, O. G. Kuzueva, C. O. Kappe, and O. N. Chupakhin. "ChemInform Abstract: Synthesis and Reactions of Biginelli Compounds. Part 18. Biginelli Condensations of Fluorinated 3-Oxo Esters and 1,3-Diketones." ChemInform 31, no. 30 (June 7, 2010): no. http://dx.doi.org/10.1002/chin.200030133.

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44

Laali, Kenneth K., Rajesh G. Kalkhambkar, and Suraj M. Sutar. "Recent Advances in the Synthesis of Diverse Libraries of Small-Molecule Building Blocks in Ionic Liquids (ILs)." Synlett 33, no. 07 (November 18, 2021): 617–36. http://dx.doi.org/10.1055/s-0040-1719852.

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AbstractThe Account describes recent advances, from the authors’ laboratories, in the synthesis of diverse libraries of small-molecule building blocks employing ionic liquids (ILs). The ability of ILs to act as catalysts/promoters/solvents for electrophilic and onium ion chemistry, as well as in metal-mediated cross-coupling reactions, and the potential to sequence/hyphenate these methods, have opened up new opportunities for facile assembly of functional small molecules with increased complexity from readily available precursors. While Brønsted acidic IL/IL solvent mixtures are suitable media for carbocation and onium ion chemistry, piperidine-appended IL/IL solvent mixtures can successfully catalyze a variety of base-catalyzed reactions. Several widely practiced transformations including ‘name reactions’ were adapted and performed efficiently in ILs.1 Introduction2 Aryldiazonium Salts and Aryltriazenes as Coupling Partners in Metal-Mediated C–C Cross-Coupling Reactions in ILs3 Expanding the Scope of Metal-Mediated Cross-Coupling Reactions in ILs4 Application of ILs in Synthesis and Functionalization of Hetero­cycles5 Expanding the Scope of Amide Synthesis in ILs6 Generation and Chemistry of ‘Tamed’ Propargylic Cations in ILs7 Newer Nitration Methods for Arenes and Heteroarenes in ILs8 Halofunctionalization in ILs9 ‘Name Reactions’and Other Widely Practiced Synthetic Transformations in ILs9.1 The Biginelli Reaction9.2 Nitrile Synthesis by the Schmidt Reaction9.3 Rupe Rearrangement9.4 Synthesis of 1,3-Dioxanes via Prins Reaction in [BMIM(SO3H)][OTf]9.5 Synthesis of Cyclopropanes and Oxiranes by the Corey–Chaykovsky (CC) Reaction10 Conclusions and Closing Remarks
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45

Suzuki, Ichiro, Yuko Suzumura, and Kei Takeda. "Metal triflimide as a Lewis acid catalyst for Biginelli reactions in water." Tetrahedron Letters 47, no. 45 (November 2006): 7861–64. http://dx.doi.org/10.1016/j.tetlet.2006.09.019.

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46

Jenner, Gérard. "Effect of high pressure on Biginelli reactions. Steric hindrance and mechanistic considerations." Tetrahedron Letters 45, no. 32 (August 2004): 6195–98. http://dx.doi.org/10.1016/j.tetlet.2004.05.106.

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47

Liu, Qingjian, Jiehua Xu, Fei Teng, Anjun Chen, Ning Pan, and Wenwen Zhang. "Studies on the Biginelli Reactions of Salicylaldehyde and 2-Hydroxy-l-naphthaldehyde." Journal of Heterocyclic Chemistry 51, no. 3 (December 3, 2013): 741–46. http://dx.doi.org/10.1002/jhet.1785.

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48

KAPPE, C. O., and S. F. FALSONE. "ChemInform Abstract: Synthesis and Reactions of Biginelli Compounds. Part 12. Polyphosphate Ester Mediated Synthesis of Dihydropyrimidines. Improved Conditions for the Biginelli Reaction." ChemInform 29, no. 43 (June 19, 2010): no. http://dx.doi.org/10.1002/chin.199843161.

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49

Stadler, Alexander, and C. Oliver Kappe. "Microwave-mediated Biginelli reactions revisited. On the nature of rate and yield enhancements." Journal of the Chemical Society, Perkin Transactions 2, no. 7 (2000): 1363–68. http://dx.doi.org/10.1039/b002697m.

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50

Cazes, Bernard, Mohamed Tabouazat, Ahmed Louzi, and Mohammed Ahmar. "Biginelli-Atwal Reactions of (+)-Pulegone: An Entry into Chiral Hexahydroquinazolin-2-one Derivatives." Synlett 2008, no. 16 (September 10, 2008): 2495–99. http://dx.doi.org/10.1055/s-2008-1078177.

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