Biginelli reaction: an overview

Nagarajaiah, H.; Mukhopadhyay, Arindam; Moorthy, Jarugu Narasimha

doi:10.1016/j.tetlet.2016.09.047

Cited by 220 publications

(138 citation statements)

References 94 publications

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“…[16] In 2011, Oberg and Rovis demonstrated that am onodentate phosphoramidite can serve as ac ompetent ligand for Rh-catalyzed [4+ +2] cycloaddition of a,b-unsaturated imines and isocyanates, [17] affording highly enantioenrichedp yrimidinones with as ubstitution pattern complementary to that of Biginelli adducts. [18] Given the remarkable biological and pharmaceuticalr elevance of the 3,4-dihydropyrimidin-2-ones, we subsequently evaluated phosphoramidite ligands 6a-m in this cycloaddition reaction, using 1,4-diphenyl-1-azabuta-1,3-diene Scheme2. Synthesis of chiral monophosphoramidite ligands 6a-m. [b] ee [%] [c] 1 [d] (9a)a nd n-hexyl isocyanate (10 a)a sm odel substrates and chloridobis(ethylene)rhodium(I) dimer as the Rh I precursor.T he reactions were generally conducted in toluene at 110 8Cf or 12 hi nt he presence of the catalyst generated in situ from 5mol %[ {Rh(C 2 H 4 ) 2 Cl} 2 ]a nd 10 mol %p hosphoramidite 6 (molar ratio Rh/L = 1:1), and the resultsa re summarized in Ta ble 3.…”

Section: Rh-catalyzed Asymmetric [4+ +2] Cycloaddition Of Ab-unsaturmentioning

confidence: 99%

Development of Chiral Spiro Phosphoramidites for Rhodium‐Catalyzed Enantioselective Reactions

Zheng

Cao

Zhu

et al. 2019

Chemistry A European J

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Aseries of 1,1'-spirobiindane-7,7'-diol (SPINOL)a nalogues bearing a2 ,2'-dimethyl-, cyclopentyl-, or cyclohexylfused ring weres ynthesized, and their distinct structural features were elucidated by X-ray crystallography. On the basis of these scaffolds,c hiral monophosphoramidite ligands 6am were synthesized,w hich demonstrated excellent enantioselectivity in Rh I -catalyzed asymmetric hydrogenation of a dehydro amino acid methyl ester.L igands 6a-m were also successfully applied in the Rh I -catalyzed enantioselective [4+ +2] cycloaddition of a,b-unsaturated imines with isocyanates,w hicha fforded the corresponding pyrimidinones in good yields (60-92 %) with high enantioselectivities (75-92 % ee).Scheme1.a) Synthesisofc hiral 2,2'-dimethylspirobiindanediols. b) Synthesis of chiral cyclopentyl-or cyclohexyl-fusedspirobiindanediols. Conditions: i) NaH (3.0 equiv),T HF,08C, 1h,t hen MeI (3.0 equiv), 0 8C!RT;ii) PPA, 105 8C, 6h;iii) nBuLi (3.0 equiv), THF, À78 8C, 1h;i v) BBr 3 (2.5 equiv), CH 2 Cl 2 , À78 8C!RT,12h; v) optical resolution by semipreparative HPLC on ac hiralcolumn.

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Section: Rh-catalyzed Asymmetric [4+ +2] Cycloaddition Of Ab-unsaturmentioning

confidence: 99%

Development of Chiral Spiro Phosphoramidites for Rhodium‐Catalyzed Enantioselective Reactions

Zheng

Cao

Zhu

et al. 2019

Chemistry A European J

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“…Dihydropyrimidones/thiones are displayed wide medicinal properties. These are calcium channel blockers, antihypertensive property, neuropeptide Y (NPY) antagonists, antitumor, antibacterial, antiviral, anti‐inflammatory, α 1 a adrenergic antagonists, mitotic kinesin inhibitors, HIVgp‐120‐CD4 inhibitors and many more . The year 1891 was a landmark in the chemistry for discovery of new class of heterocycle named dihydropyrimidones/thiones or well known Biginelli adducts.…”

Section: Introductionmentioning

confidence: 99%

Recent Advances in Homogeneous and Heterogeneous Catalyst in Biginelli Reaction from 2015‐19: A Concise Review

Chopda

Dave

2020

ChemistrySelect

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In the chemistry world, the year 1891 was considered as milestone year for the discovery of new type of heterocyclic compounds by Pietro Biginelli. The Biginelli protocol provides 3,4-dihydropyrimidin-2(1H)-ones/thiones in the presence of Bronsted acids and Lewis acids. Multifunctional Dihydropyrimidones (DHPMs) are displayed wide medicinal properties. Several of homogeneous and heterogeneous catalysts have been reported to improve the yield of product. This review includes the progress of ionic liquids, combination of ionic liquids with homogeneous & heterogeneous catalyst, homogeneous, heterogeneous and asymmetric catalyst took place in last five year (2015-2019) for Biginelli reaction. Most of catalysts showed good catalytic activity (more than 80 %) towards the synthesis of Biginelli adducts. [a] Mr. Scheme 1. Biginelli reaction. ChemistrySelect Reviews Figure 1. Structure of ionic liquids. Scheme 2. Synthesis of DHPMS by [C 3 SO 3 HDoim]HSO 4. Scheme 3. Synthesis of 7 by L-proline nitrate.ChemistrySelect Reviews

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“…The derivatives of 3,4-dihydropyrimidin-2(1H)-ones (DHPMs) as products of the Biginelli reaction are known to have various pharmacological activities, such as anticancer [1], antioxidant [2], anti-inflammation, antibacterial, and antifungal [3], anti HIV [4], and antihypertensive [5]. The discovery of 4-(3-hydroxyphenyl)-3,4-dihydropyrimidine-2(1H)-thione, which is well known as monastrol (1) as moderate anticancer agent through inhibition of the microtubule-stimulated ATPase activity of Eg5 [6] inspired researchers to use this protein as a protein target to develop new anticancer agents due to its specific function during cell cycle.…”

Section: Introductionmentioning

confidence: 99%

(E)-3-(2,5-Dimethoxyphenyl)-1-{[4-(2,5-dimethoxy-phenyl)-6-((E)-2,5-dimethoxystyryl)-2-thioxo-1,2,3,4-tetrahydropyrimidin-5-yl]}prop-2-en-1-one and (E)-3-(2,5-Dimethoxyphenyl)-1-{[4-(2,5-dimethoxyphenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidin-5-yl]}prop-2-en-1-one

Suwito

Kurnyawaty

Susetyo

et al. 2019

Molbank

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Communication (E)-3-(2,5-Dimethoxyphenyl)-1-{[4-(2,5-dimethoxyphenyl)-6-((E)-2,5-dimethoxystyryl)-2-thioxo-1,2,3, 4-tetrahydropyrimidin-5-yl]}prop-2-en-1-one and (E)-3-(2,5-Dimethoxyphenyl)-1-{[4-(2,5dimethoxyphenyl)-6-methyl-2-thioxo-1,2,3, 4-tetrahydropyrimidin-5-yl]}prop-2-en-1-one Abstract: Dihydropyrimidine derivatives possess great potential to be used as a precursor for the synthesis of wide diverse dihydropyrimidine-like derivatives. In this research, the title compounds were synthesized through the reaction between 5-acetyl-4-(2,5-dimethoxyphenyl)-6-methyl-3, 4-dihydropyrimidin-2(1H)-thione and 2,5-dimethoxybenzladehyde under aldol condensation condition. The title compound, (E)-3-(2,5-dimethoxyphenyl)-1-{[(4-(2,5-dimethoxyphenyl)-6-((E) -2,5-dimethoxystyryl)-2-thioxo-1,2,3,4-tetrahydropyrimidin-5-yl)]}prop-2-en-1-one (yield 15%), was obtained as major product, whereas (E)-3-(2,5-dimethoxyphenyl)-1-{[(4-(2,5-dimethoxyphenyl)-6-methyl -2-thioxo-1,2,3,4-tetrahydro pyrimidin-5-yl)]}prop-2-en-1-one (yield 8%) as side product through vinylogous aldol condensation.

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Biginelli reaction: an overview

Cited by 220 publications

References 94 publications

Development of Chiral Spiro Phosphoramidites for Rhodium‐Catalyzed Enantioselective Reactions

Development of Chiral Spiro Phosphoramidites for Rhodium‐Catalyzed Enantioselective Reactions

Recent Advances in Homogeneous and Heterogeneous Catalyst in Biginelli Reaction from 2015‐19: A Concise Review

(E)-3-(2,5-Dimethoxyphenyl)-1-{[4-(2,5-dimethoxy-phenyl)-6-((E)-2,5-dimethoxystyryl)-2-thioxo-1,2,3,4-tetrahydropyrimidin-5-yl]}prop-2-en-1-one and (E)-3-(2,5-Dimethoxyphenyl)-1-{[4-(2,5-dimethoxyphenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidin-5-yl]}prop-2-en-1-one

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