Page 82 - 精细化工2019年第8期

·1570· 精细化工 FINE CHEMICALS 第 36 卷

（1 mmol）尿素，2 mL EtOH，60 ℃反应 96 h。在 multicomponent Biginelli reaction: bovine serum albumin triggered
waste-free synthesis of 3, 4-dihydropyrimidin-2-(1H)-ones[J]. Amino
此条件下拓展了 11 种底物，取得了最高 63%的产 Acids, 2013, 44 (3): 1031-1037.
率。该方法反应条件较为温和，符合绿色化学的基 [18] Busto E, Gotor-Fernandez V, Gotor V. Hydrolases: Catalytically
promiscuous enzymes for non-conventional reactions in organic
本理念，但遗憾的是，该方法的产率还不够理想， synthesis[J]. Chemical Society Reviews, 2010, 39: 4504-4523.
底物适用范围也有待拓展；并且通过液相色谱测定， [19] Sun H H, Zhang H F, Ang E L, et al. Biocatalysis for the synthesis of
pharmaceuticals and pharmaceutical intermediates[J]. Bioorganic &
发现所有产物均无立体选择性。不过本研究进一步 Medicinal Chemistry, 2018, 26(7): 1275-1284.
[20] Xie Z B, Sun D Z, Jiang G F, et al. Facile synthesis of bis(indolyl)
拓展了酶非专一性的应用范围，对推动生物催化在 methanes catalyzed by α-chymotrypsin[J]. Molecules, 2014, 19(12):
有机合成中的应用仍具有积极意义。 19665-19677.
[21] Xie Zongbo (谢宗波), Zhang Shiguo (张士国), Jiang Guofang (姜国
芳), et al. pepsin-catalyzed synthesis of 2, 3-dihydroquinazolin-
参考文献： 4(1H)-onederivatives[J]. Chinese Journal of Organic Chemistry (有
[1] Puripat M, Ramozzi R, Hatanaka M, et al. ChemInform Abstract: 机化学), 2017, 37(2): 514-519.
The Biginelli reaction is a urea-catalyzed organocatalytic [22] Wu Q, Liu B K, Lin X F. Enzymatic promiscuity for organic
multicomponent reaction[J]. Cheminform, 2015, 46(37): 6959-6967. synthesis and cascade process[J]. Current Organic Chemistry, 2010,
[2] Simón L, Goodman J M. A model for the enantioselectivity of imine 14(17): 1966-1988.
reactions catalyzed by BINOL-phosphoric acid catalysts[J]. Journal [23] Chen Y L, Li W, Liu Y, et al. Trypsin-catalyzed direct asymmetric
of Organic Chemistry, 2011, 76(6): 1775-1788. aldol reaction[J]. Journal of Molecular Catalysis B-Enzymatic, 2013,
[3] Maksim A Kolosov, Olesia G Kulyk, Muataz J K, et al. An effective 87(3): 83-87.
Biginelli-type synthesis of 1-methoxy-3, 4-dihydropyrimidin- [24] Xie B H, Guan Z, He Y H. Promiscuous enzyme-catalyzed Michael
2(1H)-ones[J]. Cheminform, 2015, 46(45): 4666-4669. addition: synthesis of warfarin and derivatives[J]. Journal of
[4] Shamim Shahbaz, Khan Khalid Mohammed, Salar Uzma, et al. Chemical Technology and Biotechnology, 2012, 87(12): 1709-1714.
5-Acetyl-6-methyl-4-aryl-3, 4-dihydropyrimidin-2(1H)-ones: As [25] Xue Y, Li L P, He Y H, et al. Protease-catalysed direct asymmetric
potent urease inhibitors; synthesis, in vitro screening, and molecular Mannich reaction in organic solvent[J]. Scientific Reports, 2012,
modeling study[J]. Bioorganic Chemistry, 2018, 76: 37-52. 2(10): 761.
[5] Crespo A, El M A, Biagini P, et al. Discovery of 3, [26] Jetti S R, Jain S, Bhatewara A, et al. Silica-bonded-propyl sulfamic
4-dihydropyrimidin-2(1H)-ones as a novel class of potent and acid as an efficient recyclable catalyst for the synthesis of 3,
selective A 2B sdenosine receptor antagonists[J]. ACS Medicinal 4-dihydropyrimidin-2-(1H)-ones/thiones under heterogeneous
Chemistry Letters, 2013, 4(11): 1031-1036. conditions[J]. Chinese Chemical Letters, 2014, 25(3): 469-473.
[6] Shen Z L, Xu X P, Ji S J. ChemInform Abstract: Broensted base [27] Elhamifar D, Elhamifar D, Shojaeipoor F. Synthesis, characterization
catalyzed one-pot three-component Biginelli-type reaction: an and catalytic application of a novel polyethylene-supported Fe/ionic
efficient synthesis of 4, 5, 6-triaryl-3, 4-dihydropyrimidin-2(1H)-one liquid complex[J]. Journal of Molecular Catalysis A: Chemical, 2017,
and mechanistic study[J]. Cheminform, 2010, 41(24): 1162-1167. 426: 198-204.
[7] Bose D S, Fatima L, Mereyala H B. Green chemistry approaches to [28] Nazari S, Saadat S, Fard P K, et al. Imidazole functionalized
the synthesis of 5-alkoxycarbonyl-4-aryl-3, 4-dihydropyrimidin- magnetic Fe 3O 4 nanoparticles as a novel heterogeneous and efficient
2(1H)-ones by a three-component coupling of one-pot condensation catalyst for synthesis of dihydropyrimidinones by Biginelli
reaction: comparison of ethanol, water, and solvent-free conditions[J]. reaction[J]. Monatshefte Fur Chemie, 2013, 144(12): 1877-1882.
Journal of Organic Chemistry, 2003, 68(2): 587-590. [29] Wang J H, Zhang E, Tang G M, et al. Novel bipyridinyl
[8] Slimi H, Moussaoui Y, Salem R B. Synthesis of 3, oxadiazole-based metal coordination complexes: high efficient and
4-dihydropyrimidin-2(1H)-ones/thiones via Biginelli reaction green synthesis of 3, 4-dihydropyrimidin-2(1H)-ones through the
promoted by bismuth(Ⅲ)nitrate or PPh 3 without solvent[J]. Arabian Biginelli reactions[J]. Journal of Solid State Chemistry, 2016, 261:
Journal of Chemistry, 2016, 9: S510-S514. 86-98.
[9] Lal J, Sharma M, Sahu P K, et al. Multi-component one-pot synthesis [30] Zare A, Nasouri Z. A green approach for the synthesis of 3,
of 4-aryl substituted dihydropyrimidinones and mechanistic study 4-dihydropyrimidin-2-(1H)-ones (and-thiones) using N, N-diethyl-
under solvent-free conditions using NiO 2 as heterogeneous recyclable N-sulfoethanaminium hydrogen sulfate[J]. Journal of Molecular
green catalyst[J]. Proceedings of the National Academy of Sciences Liquids, 2016, 216: 364-369.
India, 2013, 83(3): 187-193. [31] Rashmi S V, Sandhya N C, Raghava B, et al. Trifluoroethanol as a
[10] Karimi-Jaberi Z, Moaddeli M S. Synthesis of 3, 4-dihydropyrimidin- metal-free, homogeneous, and recyclable medium for the efficient
2(1H)-ones and their corresponding 2(1H)thiones using one-pot synthesis of dihydropyrimidones[J]. Cheminform, 2012,
trichloroacetic acid as a catalyst under solvent-free conditions[J]. Isrn 42(3): 424-433.
Organic Chemistry, 2012, 2012(1/2): 1-4. [32] Maleki A, Paydar R. Bionanostructure-catalyzed one-pot three-
[11] Moussa S B, Lachheb J, Gruselle M, et al. Calcium, Barium and component synthesis of 3, 4-dihydropyrimidin-2(1H)-one derivatives
Strontium apatites: A new generation of catalysts in the Biginelli under solvent-free conditions[J]. Reactive and Functional Polymers,
reaction[J]. Tetrahedron, 2017, 73(46): 6542-6547. 2016, 109: 120-124.
[12] Nagarajaiah H, Mukhopadhyay A, Moorthy J N. Biginelli reaction: [33] Liu Z Q, Ma R, Cao D W. New efficient synthesis of 3,
An overview[J]. Tetrahedron Letters, 2016, 57(47): 5135-5149. 4-dihydropyrimidin-2(1H)-ones catalyzed by benzotriazolium-based
[13] Zheng S, Jian Y, Xu S, et al. N-Donor ligand activation of titanocene ionic liquids under solvent-free conditions[J]. Molecules, 2016,
for the Biginelli reaction via the imine mechanism[J].RSC Advances, 21(4): 462.
2018, 8(16): 8657-8661. [34] Damgaard M, Al-Khawaja A, Nittegaard-Nielsen, et al. Monastrol, a
[14] Alvim H G O, Lima T B D, Oliveira H C B D, et al. Ionic liquid 3, 4-dihydropyrimidin-2(1H)-thione, as structural scaffold for the
effect over the Biginelli reaction under homogeneous and development of modulators for GHB high-affinity binding sites and
heterogeneous catalysis[J]. ACS Catalysis, 2013, 3(3): 1420-1430. α 1β 2δ GABA A receptors[J]. European Journal of Medicinal
[15] Lei M, Ma L, Hu L. An efficient and environmentally friendly Chemistry, 2017, 138: 300-312.
procedure for synthesis of pyrimidinone derivatives by use of a [35] Liu Y, Liu R. The interaction of α-chymotrypsin with one persistent
Biginelli-type reaction[J]. Monatshefte fur Chemie, 2010, 141(9): organic pollutant (dicofol): Spectroscope and molecular modeling
1005-1008. identification[J]. Food & Chemical Toxicology, 2012, 50(9): 3298-
[16] Borse B N, Borude V S, Shukla S R. Synthesis of novel 3305.
dihydropyrimidin-2(1H)-ones derivatives using lipase and their [36] Kumar A, Venkatesu P. Overview of the stability of α-chymotrypsin
antimicrobial activity[J]. Current Chemistry Letters, 2012, 1: 59-68. in different solvent media[J]. Chemical Reviews, 2012, 112(7): 4283-
[17] Sharma U K, Sharma N, Kumar R, et al. Biocatalysts for 4307.