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Synlett
Volumn , Issue 4, 2009, Pages 599-602
Oxidation of Biginelli reaction products: Synthesis of 2-unsubstituted 1,4-dihydropyrimidines, pyrimidines, and 2-hydroxypyrimidines
Author keywords

1,4 dihydropyrimidine; 2 hydroxypyrimidine; 2 unsubstituted pyrimidine; Biginelli reaction; Desulfurative oxidation
Indexed keywords

EID: 62249208782     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0028-1087920     Document Type: Article
Times cited : (5)
References (32)
  • 14
    • 62249168347 scopus 로고    scopus 로고
    • Mitsushita, A, Oda, M, Kawachi, Y, Chika, J.-i. WO 03006437, 2003
    • Mitsushita, A.; Oda, M.; Kawachi, Y.; Chika, J.-i. WO 03006437, 2003.
  • 21
    • 62249209713 scopus 로고    scopus 로고
    • WO 2005007608
    • (b) Draper, R. W. WO 2005007608, 2005.
    • (2005)
    • Draper, R.W.1
  • 25
    • 84857417025 scopus 로고
    • in these references, pyrimidin-2-thione or its thioether derivative was reduced by Raney nickel to provide 1,4-dihydropyrimidine
    • (b) Kanina, E. L.; Mucenice, D.; Kadysh, V. P.; Duburs, G. Khim. Geterotsikl. Soedin. 1986, 1223; in these references, pyrimidin-2-thione or its thioether derivative was reduced by Raney nickel to provide 1,4-dihydropyrimidine.
    • (1986) Khim. Geterotsikl. Soedin , pp. 1223
    • Kanina, E.L.1    Mucenice, D.2    Kadysh, V.P.3    Duburs, G.4
  • 28
    • 62249145650 scopus 로고    scopus 로고
    • General Procedure for the Preparation of 1,4-Dihydropyrimidines 2a-e To a stirred mixture of 1a (1 g, 3.62 mmol) and a catalytic amount of vanadium sulfate (0.0072 g, 10 mol, in EtOH (2.5 mL) and H 2O (2.5 mL) was added dropwise 30% H2O2 (1.52 g, 13.38 mmol) over 1 h maintaining the reaction temperature at about 50°C. After 8-12 h, the mixture was cooled and volatiles were evaporated under vacuum. The mixture was diluted with CH2Cl2 (10 mL) and washed with H2O (30 mL, The separated organic layer was dried with MgSO4, filtered, and concentrated to afford crude 2a. Column chromatography with EtOAc-n-hexane gave 2a as a white solid (397 mg, 48, Spectroscopic Data Compound 2a: 1H NMR (400 MHz, DMSO-d6, δ, 9.30 (s, 1 H, 7.30-7.16 (m, 5 H, 5.40 (s, 1 H, 3.97 (q, J, 4.0 Hz, 2 H, 2.22 (s, 3 H, 1.12 t, J
    • 3): δ = 167.1, 162.5 (d, J = 250.0 Hz), 145.1, 142.6, 141.4, 129.2 (d, J = 10.0 Hz), 115.6 (d, J = 20.0 Hz), 115.5, 101.2, 60.3, 57.4, 19.5, 14.6. ESI-MS: m/z = 263.3 [M + 1].
  • 31
    • 62249084124 scopus 로고    scopus 로고
    • General Procedure for the Preparation of 2-Unsubstituted Pyrimidines 3a-e To a stirred solution of 2a (100 mg, 0.41 mmol) in acetone (2 mL) was added KMnO4 (87 mg, 0.55 mmol, After the complete consumption of 2a, excess of KMnO4 was decomposed by the addition of 2-PrOH. The reaction mixture was filtered through Celite and washed thoroughly with acetone (10 mL, Removal of solvent afforded product 3a (72mg, 73, as a white solid. Spectroscopic Data Compound 3a: 1H NMR (400 MHz, CDCl3, δ, 9.16 (s, 1 H, 7.68-7.43 (m, 5 H, 4.24 (q, J, 4.0 Hz, 2 H, 2.57 (s, 3 H, 1.10 (t, J, 2.7 Hz, 3 H, 13C NMR (100 MHz, CDCl3, δ, 167.4, 164.7, 162.9, 157.8, 137.2, 131.8, 131.5, 129.9, 128.3, 128.0, 125.7, 61.7, 22.3, 13.4. ESI-MS: m/z, 243.4 [M, 1, Compound 3b: 1H NMR(400 MHz, CDCl3, δ, 9.13 (s, 1 H, 7.60 d, J
    • 3): δ = 168.1, 164.4 (d, d, J = 230.0 Hz), 164.0, 162.4, 158.5, 134.0, 131.0 (d, J = 10.0 Hz), 126.2, 116.2 (d, J = 20.0 Hz), 62.5, 23.0, 14.1. ESI-MS: m/z = 261.3 [M + 1].
  • 32
    • 62249155675 scopus 로고    scopus 로고
    • General Procedure for the Preparation of 2-Hydroxypyrimidines 5a-e To a stirred solution of 4a (1.0 g, 3.84 mmol) in acetone (20 mL) was added KMnO4 (1.52 g, 9.60 mmol, After the complete consumption of 4a, the excess KMnO4 was decomposed by the addition of 2-PrOH. The reaction mixture was filtered through Celite and washed thoroughly with acetone (30 mL, Removal of solvent afforded product 5a (670mg, 81, as a white solid. Spectroscopic Data Compound 5a: 1H NMR (400 MHz, CDCl3, δ, 7.61-7.41 (m, 5 H, 4.05 (q, J, 4.0 Hz, 2 H, 2.62 (s, 3 H, 0.94 (t, J, 2.7 Hz, 3 H, 13C NMR (100 MHz, CDCl3, δ, 167.4, 164.7, 162.9, 157.8, 137.2, 131.8, 131.7, 131.5, 129.9, 128.3, 128.0, 125.7, 61.7, 22.3, 13.4. ESI-MS: m/z, 259.3 [M, 1, Compound 5b: 1H NMR (400 MHz, CDCl3, δ, 7.52-7.13 (m, 4 H, 4.80-4.26 m, 2 H, 3
    • 3): δ = 165.5, 162.4 (d, J = 250.0 Hz), 146.4, 139.7, 139.6, 128.4 (d, J = 10.0 Hz), 115.5 (d, J = 20.0 Hz), 101.4, 60.1, 55.0, 18.5, 14.2. ESI-MS: m/z = 277.3 [M + 1].

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.