메뉴 건너뛰기




Volumn 38, Issue 8, 2008, Pages 1299-1310

New procedure for one-pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones by Biginelli reaction

Author keywords

Biginelli reaction; Heterocycle; Lewis acids; Surfactant

Indexed keywords

5 ACETYL 4 (2 CHLOROPHENYL) 6 METHYL 3,4 DIHYDROPYRIMIDIN 2(1H) ONE; 5 ACETYL 4 (2 HYDROXY 3 METHOXYPHENYL) 6 METHYL 3,4 DIHYDROPYRIMIDIN 2(1H) ONE; 5 ACETYL 4 (4 CHLOROPHENYL) 6 METHYL 3,4 DIHYDROPYRIMIDIN 2(1H) ONE; 5 ACETYL 4 (FURAN 2 YL) 6 METHYL 3,4 DIHYDROPYRIMIDIN 2(1H) ONE; 5 ACETYL 6 METHYL 4 (2,3,4 TRIMETHOXYPHENYL) 3,4 DIHYDROPYRIMIDIN 2(1H) ONE; 5 ACETYL 6 METHYL 4 (3 NITROPHENYL) 3,4 DIHYDROPYRIMIDIN 2(1H) ONE; 5 ACETYL 6 METHYL 4 (4 NITROPHENYL) 3,4 DIHYDROPYRIMIDIN 2(1H) ONE; 5 ACETYL 6 METHYL 4 PHENYL 3,4 DIHYDROPYRIMIDIN 2(1H) ONE; ALDEHYDE; COPPER CHLORIDE; ESTER DERIVATIVE; HETEROCYCLIC COMPOUND; LEWIS ACID; PYRIMIDINONE DERIVATIVE; SURFACTANT; UNCLASSIFIED DRUG; URIC ACID; WATER;

EID: 41449094299     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910701873524     Document Type: Article
Times cited : (31)

References (36)
  • 1
    • 0027205552 scopus 로고
    • 100 years of the Biginelli dihydropyrimidine synthesis
    • Kappe, C. O. 100 years of the Biginelli dihydropyrimidine synthesis. Tetrahedron 1993, 49, 6937-6963.
    • (1993) Tetrahedron , vol.49 , pp. 6937-6963
    • Kappe, C.O.1
  • 2
    • 0031584880 scopus 로고    scopus 로고
    • Conformational analysis of 4-aryl-dihydropyrimidine calcium channel modulators. A comparison of ab initio, semiempirical and X-ray crystallographic studies
    • (a) Kappe, C. O.; Fabian, W. M.F. Conformational analysis of 4-aryl-dihydropyrimidine calcium channel modulators. A comparison of ab initio, semiempirical and X-ray crystallographic studies. Tetrahedron 1997, 53, 2803-2816;
    • (1997) Tetrahedron , vol.53 , pp. 2803-2816
    • Kappe, C.O.1    Fabian, W.M.F.2
  • 3
    • 41449091104 scopus 로고    scopus 로고
    • Atwal, K. S.; Roonyak, G. C.O.; Schwartz, B. C. Substituted 1,4-dihydropyrimidines.
    • (b) Atwal, K. S.; Roonyak, G. C.O.; Schwartz, B. C. Substituted 1,4-dihydropyrimidines.
  • 4
    • 0024818583 scopus 로고
    • Synthesis of selectively functionalized 2-hetero-1,4-dihydropyrimidines
    • Synthesis of selectively functionalized 2-hetero-1,4-dihydropyrimidines. J. Org. Chem. 1989, 54, 5898-5907.
    • (1989) J. Org. Chem , vol.54 , pp. 5898-5907
  • 6
    • 0030599231 scopus 로고    scopus 로고
    • Synthesis of the tricyclic portions of batzelladines A, B and D: Revision of the stereochemistry of batzelladines A and D
    • (b) Snider, B. B.; Chen, J.; Patil, A. D.; Freyer, A. Synthesis of the tricyclic portions of batzelladines A, B and D: revision of the stereochemistry of batzelladines A and D. Tetrahedron Lett. 1996, 37, 6977-6980.
    • (1996) Tetrahedron Lett , vol.37 , pp. 6977-6980
    • Snider, B.B.1    Chen, J.2    Patil, A.D.3    Freyer, A.4
  • 7
    • 1342302935 scopus 로고    scopus 로고
    • The tethered Biginelli condensation in natural product synthesis
    • Aron, Z. D.; Overman, L. E. The tethered Biginelli condensation in natural product synthesis. Chem. Commun. 2004, 253-265.
    • (2004) Chem. Commun , pp. 253-265
    • Aron, Z.D.1    Overman, L.E.2
  • 8
    • 9344256322 scopus 로고
    • Synthesis of tetrahydropyrimidinones by the acid-catalyzed condensation of an aldehyde, a β-keto ester and urea
    • Biginelli, P. G. Synthesis of tetrahydropyrimidinones by the acid-catalyzed condensation of an aldehyde, a β-keto ester and urea. Chim. Ital. 1893, 26, 447-449.
    • (1893) Chim. Ital , vol.26 , pp. 447-449
    • Biginelli, P.G.1
  • 9
    • 0036193521 scopus 로고    scopus 로고
    • Lu, J.; Bai, Y. Catalysis of the Biginelli Reaction by ferric and nickel chloride hexahydrates: one-pot synthesis of 3,4-dihydropyrimidin- 2(1H)-ones synthesis. Synthesis 2002, 466-470;
    • (a) Lu, J.; Bai, Y. Catalysis of the Biginelli Reaction by ferric and nickel chloride hexahydrates: one-pot synthesis of 3,4-dihydropyrimidin- 2(1H)-ones synthesis. Synthesis 2002, 466-470;
  • 10
    • 0037462396 scopus 로고    scopus 로고
    • Bose, D. S.; Fatima, L.; Mereyala, H. B. Green chemistry approaches to the synthesis of 5-alkoxycarbonyl- 4-aryl-3,4-dihydropyrimidin-2(1H)- ones by a three-component coupling of one-pot condensation reaction: comparison of ethanol, water, and solvent-free conditions. J. Org. Chem. 2003, 68, 587-590;
    • (b) Bose, D. S.; Fatima, L.; Mereyala, H. B. Green chemistry approaches to the synthesis of 5-alkoxycarbonyl- 4-aryl-3,4-dihydropyrimidin-2(1H)- ones by a three-component coupling of one-pot condensation reaction: comparison of ethanol, water, and solvent-free conditions. J. Org. Chem. 2003, 68, 587-590;
  • 11
    • 0035969014 scopus 로고    scopus 로고
    • 2O-mediated three-component, one-pot, condensation reaction: an efficient synthesis of 4-aryl-substituted 3,4-dihydropyrimidin-2-ones. Tetrahedron Lett. 2001, 42, 7873-7875;
    • 2O-mediated three-component, one-pot, condensation reaction: an efficient synthesis of 4-aryl-substituted 3,4-dihydropyrimidin-2-ones. Tetrahedron Lett. 2001, 42, 7873-7875;
  • 12
    • 0036532558 scopus 로고    scopus 로고
    • Reddy, C. V.; Mahesh, M.; Raju, P. V.K.; Babu, T. R.; Reddy, V. V.N. Zirconium(IV) chloride catalyzed one-pot synthesis of 3,4-dihydropyrimidin- 2(1H)-ones. Tetrahedron Lett. 2002, 43, 2657-2659;
    • (d) Reddy, C. V.; Mahesh, M.; Raju, P. V.K.; Babu, T. R.; Reddy, V. V.N. Zirconium(IV) chloride catalyzed one-pot synthesis of 3,4-dihydropyrimidin- 2(1H)-ones. Tetrahedron Lett. 2002, 43, 2657-2659;
  • 13
    • 0034703416 scopus 로고    scopus 로고
    • Indium(III) chloride-catalyzed one-pot synthesis of dihydropyrimidinones by a three-component coupling of 1,3-dicarbonyl compounds, aldehydes, and urea: An improved procedure for the Biginelli reaction
    • (e) Ranu, B. C.; Hajra, A.; Jana, U. Indium(III) chloride-catalyzed one-pot synthesis of dihydropyrimidinones by a three-component coupling of 1,3-dicarbonyl compounds, aldehydes, and urea: An improved procedure for the Biginelli reaction. J. Org. Chem. 2000, 65, 6270-6272;
    • (2000) J. Org. Chem , vol.65 , pp. 6270-6272
    • Ranu, B.C.1    Hajra, A.2    Jana, U.3
  • 15
    • 0034986934 scopus 로고    scopus 로고
    • Bismuth(III)- catalyzed synthesis of dihydropyrimidinones: Improved protocol conditions for the Biginelli reaction
    • (g) Ramaliga, K.; Vijayalakshmi, P.; Kaimal, T. N.B. Bismuth(III)- catalyzed synthesis of dihydropyrimidinones: improved protocol conditions for the Biginelli reaction. Synlett. 2001, 863-865;
    • (2001) Synlett , pp. 863-865
    • Ramaliga, K.1    Vijayalakshmi, P.2    Kaimal, T.N.B.3
  • 16
    • 0034684498 scopus 로고    scopus 로고
    • Lu, J.; Bai, Y.; Wang, Z.; Yang, B.; Ma, H. One-pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones using lanthanum chloride as a catalyst. Tetrahedron Lett. 2000, 41, 9075-9078;
    • (h) Lu, J.; Bai, Y.; Wang, Z.; Yang, B.; Ma, H. One-pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones using lanthanum chloride as a catalyst. Tetrahedron Lett. 2000, 41, 9075-9078;
  • 17
    • 23044493101 scopus 로고    scopus 로고
    • De, S. K.; Gibbs, R. A. Ruthenium(III) chloride-catalyzed one-pot synthesis of 3,4-dihydropyrimidin-2-(1H)-ones under solvent-free conditions synthesis 2005, 1748-1750;
    • (i) De, S. K.; Gibbs, R. A. Ruthenium(III) chloride-catalyzed one-pot synthesis of 3,4-dihydropyrimidin-2-(1H)-ones under solvent-free conditions synthesis 2005, 1748-1750;
  • 18
    • 33748456980 scopus 로고    scopus 로고
    • Liu, C. J.; Wang, J. D.; Li, Y. P. One-pot synthesis of 3,4-dihydropyrimidin- 2(1H)-(thio)ones using strontium(II) nitrate as a catalyst. J. Mol. Catal. A: Chem. 2006, 258, 367-370;
    • (j) Liu, C. J.; Wang, J. D.; Li, Y. P. One-pot synthesis of 3,4-dihydropyrimidin- 2(1H)-(thio)ones using strontium(II) nitrate as a catalyst. J. Mol. Catal. A: Chem. 2006, 258, 367-370;
  • 19
    • 33845973414 scopus 로고    scopus 로고
    • Kalita, H. R.; Phukan, P. CuI as reusable catalyst for the Biginelli reaction. Catal. Commun. 2007, 8, 179-182;
    • (k) Kalita, H. R.; Phukan, P. CuI as reusable catalyst for the Biginelli reaction. Catal. Commun. 2007, 8, 179-182;
  • 20
    • 1242341296 scopus 로고    scopus 로고
    • Gohain, M.; Prajapati, D.; Sandhu, J. S. A novel Cu-catalyzed three-component one-pot synthesis of dihydropyrimidiu-2(1H)-ones using microwaves under solvent-free condition. Synlett. 2004, 235-238.
    • (l) Gohain, M.; Prajapati, D.; Sandhu, J. S. A novel Cu-catalyzed three-component one-pot synthesis of dihydropyrimidiu-2(1H)-ones using microwaves under solvent-free condition. Synlett. 2004, 235-238.
  • 21
    • 0037436897 scopus 로고    scopus 로고
    • 2: a reusable catalyst for high-yield synthesis of 3,4-dihydropyrimidin-2(1H)- ones. Tetrahedron Lett. 2003, 44, 3305-3308;
    • 2: a reusable catalyst for high-yield synthesis of 3,4-dihydropyrimidin-2(1H)- ones. Tetrahedron Lett. 2003, 44, 3305-3308;
  • 22
    • 33646869025 scopus 로고    scopus 로고
    • 2 under ultrasound irradiation. J. Mol. Catal A: Chem. 2006, 253, 207-211;
    • 2 under ultrasound irradiation. J. Mol. Catal A: Chem. 2006, 253, 207-211;
  • 23
    • 2542450906 scopus 로고    scopus 로고
    • 3-catalysed one-pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones. J. Mol. Catal. A: Chem. 2004, 217, 47-50;
    • 3-catalysed one-pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones. J. Mol. Catal. A: Chem. 2004, 217, 47-50;
  • 24
    • 33749253108 scopus 로고    scopus 로고
    • Metal triflimide as a lewis acid catalyst for Biginelli reactions in water
    • (d) Ichiro, S.; Yuko, S.; Takeda, K. Metal triflimide as a lewis acid catalyst for Biginelli reactions in water. Tetrahedron Lett. 2006, 47, 7861-7864;
    • (2006) Tetrahedron Lett , vol.47 , pp. 7861-7864
    • Ichiro, S.1    Yuko, S.2    Takeda, K.3
  • 25
    • 0034674766 scopus 로고    scopus 로고
    • On the conformational properties of [n]cyclophanes: A new application of the ramachandran plot using crystallographic data
    • (e) Ma, Y.; Qian, C.; Wang, L.; Yang, M. On the conformational properties of [n]cyclophanes: a new application of the ramachandran plot using crystallographic data. J. Org. Chem. 2000, 65, 3864-3849;
    • (2000) J. Org. Chem , vol.65 , pp. 3864-3849
    • Ma, Y.1    Qian, C.2    Wang, L.3    Yang, M.4
  • 26
    • 0038752672 scopus 로고    scopus 로고
    • Wang, L.; Qian, C.; Tian, H.; Ma, Y. Lanthanide triflate catalyzed one-pot synthesis of dihydropyrimidin-2(1H)-thiones by a three-component of 1,3-dicarbonyl compounds, aldehydes, and thiourea using a solvent-free Biginelli condensation. Synth. Commun. 2003, 33, 1459-1468;
    • (f) Wang, L.; Qian, C.; Tian, H.; Ma, Y. Lanthanide triflate catalyzed one-pot synthesis of dihydropyrimidin-2(1H)-thiones by a three-component of 1,3-dicarbonyl compounds, aldehydes, and thiourea using a solvent-free Biginelli condensation. Synth. Commun. 2003, 33, 1459-1468;
  • 27
    • 0043032892 scopus 로고    scopus 로고
    • Model studies toward the synthesis of dihydropyrimidinyl and pyridyl α-amino acids via three-component Biginelli and Hantzsch cyclocondensations
    • (g) Dondoni, A.; Massi, A.; Minghini, E.; Sabbatini, S.; Bertolasi, V. Model studies toward the synthesis of dihydropyrimidinyl and pyridyl α-amino acids via three-component Biginelli and Hantzsch cyclocondensations. J. Org. Chem. 2003, 68, 6172-6183.
    • (2003) J. Org. Chem , vol.68 , pp. 6172-6183
    • Dondoni, A.1    Massi, A.2    Minghini, E.3    Sabbatini, S.4    Bertolasi, V.5
  • 28
    • 0030913328 scopus 로고    scopus 로고
    • 3-catalyzed aqueous aldol reactions of silyl enol ethers with aldehydes in the presence of a surfactant
    • 3-catalyzed aqueous aldol reactions of silyl enol ethers with aldehydes in the presence of a surfactant. Tetrahedron Lett. 1997, 38, 4559-4562;
    • (1997) Tetrahedron Lett , vol.38 , pp. 4559-4562
    • Kobayashi, S.1    Wakabayashi, T.2    Nagayama3    Oyamada, S.H.4
  • 29
  • 31
    • 24044470646 scopus 로고    scopus 로고
    • Organic reaction in aqueous media with a focus on carbon-carbon bond formations: A decade update
    • (d) Li, C. J. Organic reaction in aqueous media with a focus on carbon-carbon bond formations: a decade update. Chem. Rev. 2005, 105, 3095-3165;
    • (2005) Chem. Rev , vol.105 , pp. 3095-3165
    • Li, C.J.1
  • 32
    • 0036703508 scopus 로고    scopus 로고
    • Stereoselective organic reactions in water
    • (e) Lindstrom, U. M. Stereoselective organic reactions in water. Chem. Rev. 2002, 102, 2751-2772.
    • (2002) Chem. Rev , vol.102 , pp. 2751-2772
    • Lindstrom, U.M.1
  • 33
    • 0030593690 scopus 로고    scopus 로고
    • Micellar solutions as reaction media
    • Tascioglu, S. Micellar solutions as reaction media. Tetrahedron 1996, 52, 11113-11152.
    • (1996) Tetrahedron , vol.52 , pp. 11113-11152
    • Tascioglu, S.1
  • 36
    • 0033958880 scopus 로고    scopus 로고
    • Iron(III)-catalyzed synthesis of dihydropyrimidinones: Improved conditions for the Biginelli reaction
    • Lu, J.; Ma, H. Iron(III)-catalyzed synthesis of dihydropyrimidinones: improved conditions for the Biginelli reaction. Synlett 2000, 63-64.
    • (2000) Synlett , pp. 63-64
    • Lu, J.1    Ma, H.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.