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Synlett
Volumn , Issue 11, 2008, Pages 1693-1697
The first tandem acetalization/5-exo-dig cyclization of 6-phenylethynylpyrimidine-5-carbaldehydes: Efficient synthesis of 5-alkoxy-(7Z)-7-benzylidene-5,7-dihydrofuro[3,4-d]pyrimidines
Author keywords

5 exo dig cyclization; 6 phenylethynylpyrimidine 5 carbaldehydes; Acetalization; Furo 3,4 d pyrimidines; Tandem reactions
Indexed keywords

ALDEHYDE DERIVATIVE; PYRIMIDINE DERIVATIVE;
EID: 48249154636     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1077824     Document Type: Article
Times cited : (21)
References (21)
  • 1
    • 0003799267 scopus 로고
    • Stang, P. J, Diederich, F, Eds, Wiley-VCH: Weinheim, Germany
    • (a) Modern Acetylene Chemistry; Stang, P. J.; Diederich, F., Eds.; Wiley-VCH: Weinheim, Germany, 1995.
    • (1995) Modern Acetylene Chemistry
  • 16
    • 48249152107 scopus 로고    scopus 로고
    • Crystal structure analysis for 3a: C39H 46N6O5S2, Mr, 742.952 g mol-1, triclinic, space group P1, a, 11.8827(4, b, 12.5375(5, c, 15.1461(7) Å, α, 104.514(3)°, β, 102.61(2)°, γ, 110.72(2)°, V, 1922.04(13) Å3, ρ, 1.284 g-cm3, F(000, 788. X-ray diffraction data were collected on a Nonius Kappa CCD diffractometer at 293 K using graphite-monochromated MoKαradiation λ, 0.71073 Å, The structure of 3a was solved by direct methods with SIR97 program13 and refined by full-matrix least squares techniques with anisotropic non-hydrogen atoms. Hydrogen atoms were refined in the riding model. The refinement calculations were carried out with the help of SHELX97 program.14 ORTEP15 view of the molecule is shown in Figure 1. Crystallographic data for the structure
    • 15 view of the molecule is shown in Figure 1. Crystallographic data for the structure of 3a have been deposited at the Cambridge Crystallographic Data Centre (CCDC number 681988).
  • 17
    • 48249110861 scopus 로고    scopus 로고
    • Typical Procedure for the Preparation of 2,4-Disubstituted 6-Phenylethynylpyrimidine-5-carbaldehydes 2a-k: A mixture of the corresponding compound 1a-k (1.15 mmol, PdCl2(PPh 3)2 (0.016 g, 0.023 mmol, CuI (0.0022 g, 0.0115 mmol, Et3N (0.23 g, 2.30 mmol) and DMF (10 mL) was stirred under Ar atmosphere for 3 min. Then phenylacetylene (0.14 g, 1.38 mmol) was added, the mixture was flushed with Ar and heated under stirring at 40 °C for 3 h. After cooling to r.t, the precipitate was filtered off and recrystallized to give compounds 2a-k. 2-Methylthio-6-phenylethynyl-4-pyrrolidin-1- ylpyrimidine-5-carbaldehyde (2a, yield: 90, mp 173-175 °C (2-PrOH, IR(KBr, 2219 (C≡C, 1665 (C=0) cm-1. 1H NMR (300 MHz, CDCl3, δ, 2.00 [br s, 4 H, CH2) 2, 2.57 (s, 3 H, SMe, 3.54 [br s, 4 H, N(CH2) 2, 7.40-7.44 (m, 3 H, ArH, 7.63-7.66 m, 2
    • 2S: C, 69.54; H, 4.38; N, 12.17. Found: C, 69.48; H, 4.39; N, 12.32.
  • 18
    • 48249105036 scopus 로고    scopus 로고
    • Typical Procedure for the Preparation of 2,4-Disubstituted 5-Alkoxy-(7Z)-7-benzylidene-5,7-dihydrofuro[3,4-d]pyrimidines 3a-p: To a solution of the corresponding 6-phenylethynylpyrirnidine-5-carbaldehyde 2a-g (0.3 mmol) in an alcohol (5 mL) a solution of the base (0.3 mmol) in appropriate alcohol (2 mL) was added. The resulting reaction mixture was refluxed for the indicated period of time (Table 1, The solvent was evaporated under reduced pressure, the residue washed with H2O, filtered and recrystallized to give compounds 3a-p, 7Z)-7-Benzylidene-5- methoxy-2-methylthio-4-pyrrolidin-l-yl-5,7-dihydrofuro[3,4-d]pyrimidine(3a, yield: 49, using t-BuNH2, 73, using K2CO 3, 95, using MeONa, mp 122-124 °C (2-PrOH, 1H NMR (300 MHz, CDCl3, δ, 1.97-2.00 [m, 4 H, CH2) 2, 2.60 (s, 3 H, SMe, 3.49 (s, 3 H, OMe, 3.72-3.88 [m, 4 H, NCH2
    • 13C NMR spectroscopic and microanalytical data.
  • 21
    • 0003625335 scopus 로고
    • Oak Ridge National Laboratory: Oak Ridge, TN, USA
    • Johnson, C. K. ORTEP-II, Report ORNL-5138; Oak Ridge National Laboratory: Oak Ridge, TN, USA, 1976.
    • (1976) ORTEP-II, Report ORNL-5138
    • Johnson, C.K.1

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.