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Volumn , Issue 12, 2007, Pages 1905-1908

Biorenewable resources in the biginelli reaction: Cerium(III)-catalyzed synthesis of novel iminosugar-annulated perhydropyrimidines

Author keywords

Biginelli reaction; Iminosugars; Microwaves; Perhydropyrimidines; Solvent free; Stereoselective

Indexed keywords

2 PHENYL 1,3 OXAZOL 5 ONE; 5 AMINOPERHYDROPYRIMIDINEDIONE DERIVATIVE; ALDEHYDE; CERIUM; IMINOSUGAR; PERHYDROPYRIMIDINE DERIVATIVE; PYRIMIDINE DERIVATIVE; THIOUREA; UNCLASSIFIED DRUG; UREA;

EID: 34547632759     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-984527     Document Type: Article
Times cited : (38)

References (42)
  • 3
    • 77957027039 scopus 로고
    • Studies in Natural Products Chemistry
    • Elsevier: Amsterdam
    • (a) Nishimura, Y. Studies in Natural Products Chemistry, Vol. 16; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, 1995, 75-121.
    • (1995) Atta-ur-Rahman, Ed , vol.16 , pp. 75-121
    • Nishimura, Y.1
  • 9
    • 0000584109 scopus 로고    scopus 로고
    • Barton, D, Nakanishi, K, Eds, Elsevier: New York
    • (b) Elbein, A. D.; Molyneux, R. J. In Comprehensive Natural Products, Vol. 3; Barton, D.; Nakanishi, K., Eds.; Elsevier: New York, 1999, 129-160.
    • (1999) Comprehensive Natural Products , vol.3 , pp. 129-160
    • Elbein, A.D.1    Molyneux, R.J.2
  • 32
    • 34547615310 scopus 로고    scopus 로고
    • General Procedure for Iminosugar-Annulated Perhydropyrimidines 4 and 5: A solvent-free mixture of oxazolone 1 (2.0 mmol, aldose 2 (2.0 mmol, urea/thiourea 3 (2.0 mmol) and Ce2(SO 4)3 (0.114 g, 10 mol, was taken in a 20-mL vial and subjected to MW irradiation for 8-13 min (Table 1, After completion of the reaction as indicated by TLC, H2O (10 mL) was added to the reaction mixture and stirred for 10 min. The yellowish precipitate thus obtained was washed with H2O to give the crude product which was recrystallized from EtOH to afford a diastereomeric mixture (>94:<6; in the crude products the ratio was >91:<9, as determined by 1H NMR spectroscopy, The product on second recrystallization from EtOH furnished an analytically pure sample of a single diastereomer 4 or 5 Table 1, On the basis of comparison of J values with the literature ones, 24,30-36
    • 7: C, 52.60; H, 5.24; N, 11.50. Found: C, 52.89; H, 5.59; N, 11.33.
  • 33
    • 34547626175 scopus 로고    scopus 로고
    • General Procedure for 5-Aminoperhydropyrimidine-dione Analogues 9 and 10: Compound 4 or 5 (2.0 mmol) was refluxed in H 2SO4-H2o (15 mL, 4:3) for 45 min in an oil bath. The reaction mixture was cooled, the desired products 9 or 10 were precipitated by adding coned NH4OH (specific gravity 0.88) under ice cooling and recrystallized from EtOH to obtain analytically pure samples of 9 and 10, respectively. Characterization Data of Representative Compounds: Compound 9a: pale yellow powder; mp 134-135°C. IR (KBr, 3345, 3011, 1683, 1669, 1605, 1579, 1451 cm -1. 1H NMR (400 MHz, DMSO-d6, D 2O, δ, 2.67 (dd, J6ax,eq, 13.1 Hz, J6ax,7h, 9.8 Hz, 1 H, H-6ax, 3.35 ddd, J7,8, 9.3 Hz, J6ax,7h, 9.8 Hz, J6eq,7h, 3.8 Hz, 1 H, H-7
    • 6: C, 41.38; H, 5.79; N, 16.09. Found: C, 41.18; H, 5.58; N, 16.21.
  • 35
    • 34547628332 scopus 로고    scopus 로고
    • General Procedure for Isolation of Michael Adducts 7a (n, 3, X, O, R, H) and 7j (n, 4, X, S, R, Ph) and Their Conversion into the Corresponding Sugar-Annulated Products 4a and 5d: The procedure followed was the same as described above for the synthesis of 4 and 5 except that the time of MW irradiation in this case was 4-6 min instead of 8-13 min. The adducts 7 were recrystallized from EtOH to give a diastereomeric mixture (>94:<6; in the crude products the ratio was >91:<9, as determined by 1H NMR spectroscopy) which was again recrystallized from EtOH to obtain an analytical sample of 7a and 7j. The adducts 7a and 7j were assigned the anti stereochemistry as their 1H NMR spectra exhibited higher values of coupling constant (JcyclicNCH,acyclicNCH, 9-9 Hz) than that of the very minor (<6, diastereomer syn, JcyclicNCH,acyclicNCH, 4
    • 7: C, 50.99; H, 5.42; N, 11.89. Found: C, 50.79; H, 5.78; N, 11.63.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.