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Volumn 4, Issue 2, 1998, Pages 157-162

Synthesis and Structural Insights of Novel 2-Diethylamino-6-methyl-4(3H)-pyrimidinones

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EID: 2742539779     PISSN: 07930283     EISSN: None     Source Type: Journal    
DOI: 10.1515/HC.1998.4.2.157     Document Type: Article
Times cited : (3)

References (58)
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    • For experimental studies on the tautomerism of 4-pyrimidinone see: a) D. J. Brown and L. N. Short, J. Chem. Soc. 331 (1953) b) D. J. Brown, E. Hoerger and S. F. Mason, J. Chem. Soc. 211 (1955) c) A. Albert and E. Spinner, J. Chem. Soc. 1221 (1960) d) Y. Inoue, N. Furutachi and K. Nakanishi, J. Org. Chem. 31, 175 (1966) e) M. J. Nowak and K. Szczepaniak, J. Mol. Struct. 62, 47 (1980) f) L. Lapinski, J. Fulara and M. J. Nowak, Spectrochimica Acta 46A, 61 (1990); For experimental studies on the tautomerism of isocytosine see: g) M. M. Stimson and M. J. O'Donnell, J. Am. Chem. Soc. 74, 1805 (1952) h) B. D. Sharma and J. F. McConnell, Acta Crystallogr. 19, 797 (1965) J. Smets, L. Adamowicz and Guido Maes, J. Mol. Struct. 322, 113 (1994).
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    • For experimental studies on the tautomerism of 4-pyrimidinone see: a) D. J. Brown and L. N. Short, J. Chem. Soc. 331 (1953) b) D. J. Brown, E. Hoerger and S. F. Mason, J. Chem. Soc. 211 (1955) c) A. Albert and E. Spinner, J. Chem. Soc. 1221 (1960) d) Y. Inoue, N. Furutachi and K. Nakanishi, J. Org. Chem. 31, 175 (1966) e) M. J. Nowak and K. Szczepaniak, J. Mol. Struct. 62, 47 (1980) f) L. Lapinski, J. Fulara and M. J. Nowak, Spectrochimica Acta 46A, 61 (1990); For experimental studies on the tautomerism of isocytosine see: g) M. M. Stimson and M. J. O'Donnell, J. Am. Chem. Soc. 74, 1805 (1952) h) B. D. Sharma and J. F. McConnell, Acta Crystallogr. 19, 797 (1965) J. Smets, L. Adamowicz and Guido Maes, J. Mol. Struct. 322, 113 (1994).
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    • For experimental studies on the tautomerism of 4-pyrimidinone see: a) D. J. Brown and L. N. Short, J. Chem. Soc. 331 (1953) b) D. J. Brown, E. Hoerger and S. F. Mason, J. Chem. Soc. 211 (1955) c) A. Albert and E. Spinner, J. Chem. Soc. 1221 (1960) d) Y. Inoue, N. Furutachi and K. Nakanishi, J. Org. Chem. 31, 175 (1966) e) M. J. Nowak and K. Szczepaniak, J. Mol. Struct. 62, 47 (1980) f) L. Lapinski, J. Fulara and M. J. Nowak, Spectrochimica Acta 46A, 61 (1990); For experimental studies on the tautomerism of isocytosine see: g) M. M. Stimson and M. J. O'Donnell, J. Am. Chem. Soc. 74, 1805 (1952) h) B. D. Sharma and J. F. McConnell, Acta Crystallogr. 19, 797 (1965) J. Smets, L. Adamowicz and Guido Maes, J. Mol. Struct. 322, 113 (1994).
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    • Inoue, Y.1    Furutachi, N.2    Nakanishi, K.3
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    • 0346271873 scopus 로고
    • For experimental studies on the tautomerism of 4-pyrimidinone see: a) D. J. Brown and L. N. Short, J. Chem. Soc. 331 (1953) b) D. J. Brown, E. Hoerger and S. F. Mason, J. Chem. Soc. 211 (1955) c) A. Albert and E. Spinner, J. Chem. Soc. 1221 (1960) d) Y. Inoue, N. Furutachi and K. Nakanishi, J. Org. Chem. 31, 175 (1966) e) M. J. Nowak and K. Szczepaniak, J. Mol. Struct. 62, 47 (1980) f) L. Lapinski, J. Fulara and M. J. Nowak, Spectrochimica Acta 46A, 61 (1990); For experimental studies on the tautomerism of isocytosine see: g) M. M. Stimson and M. J. O'Donnell, J. Am. Chem. Soc. 74, 1805 (1952) h) B. D. Sharma and J. F. McConnell, Acta Crystallogr. 19, 797 (1965) J. Smets, L. Adamowicz and Guido Maes, J. Mol. Struct. 322, 113 (1994).
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    • For experimental studies on the tautomerism of 4-pyrimidinone see: a) D. J. Brown and L. N. Short, J. Chem. Soc. 331 (1953) b) D. J. Brown, E. Hoerger and S. F. Mason, J. Chem. Soc. 211 (1955) c) A. Albert and E. Spinner, J. Chem. Soc. 1221 (1960) d) Y. Inoue, N. Furutachi and K. Nakanishi, J. Org. Chem. 31, 175 (1966) e) M. J. Nowak and K. Szczepaniak, J. Mol. Struct. 62, 47 (1980) f) L. Lapinski, J. Fulara and M. J. Nowak, Spectrochimica Acta 46A, 61 (1990); For experimental studies on the tautomerism of isocytosine see: g) M. M. Stimson and M. J. O'Donnell, J. Am. Chem. Soc. 74, 1805 (1952) h) B. D. Sharma and J. F. McConnell, Acta Crystallogr. 19, 797 (1965) J. Smets, L. Adamowicz and Guido Maes, J. Mol. Struct. 322, 113 (1994).
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    • Lapinski, L.1    Fulara, J.2    Nowak, M.J.3
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    • For experimental studies on the tautomerism of 4-pyrimidinone see: a) D. J. Brown and L. N. Short, J. Chem. Soc. 331 (1953) b) D. J. Brown, E. Hoerger and S. F. Mason, J. Chem. Soc. 211 (1955) c) A. Albert and E. Spinner, J. Chem. Soc. 1221 (1960) d) Y. Inoue, N. Furutachi and K. Nakanishi, J. Org. Chem. 31, 175 (1966) e) M. J. Nowak and K. Szczepaniak, J. Mol. Struct. 62, 47 (1980) f) L. Lapinski, J. Fulara and M. J. Nowak, Spectrochimica Acta 46A, 61 (1990); For experimental studies on the tautomerism of isocytosine see: g) M. M. Stimson and M. J. O'Donnell, J. Am. Chem. Soc. 74, 1805 (1952) h) B. D. Sharma and J. F. McConnell, Acta Crystallogr. 19, 797 (1965) J. Smets, L. Adamowicz and Guido Maes, J. Mol. Struct. 322, 113 (1994).
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    • For experimental studies on the tautomerism of 4-pyrimidinone see: a) D. J. Brown and L. N. Short, J. Chem. Soc. 331 (1953) b) D. J. Brown, E. Hoerger and S. F. Mason, J. Chem. Soc. 211 (1955) c) A. Albert and E. Spinner, J. Chem. Soc. 1221 (1960) d) Y. Inoue, N. Furutachi and K. Nakanishi, J. Org. Chem. 31, 175 (1966) e) M. J. Nowak and K. Szczepaniak, J. Mol. Struct. 62, 47 (1980) f) L. Lapinski, J. Fulara and M. J. Nowak, Spectrochimica Acta 46A, 61 (1990); For experimental studies on the tautomerism of isocytosine see: g) M. M. Stimson and M. J. O'Donnell, J. Am. Chem. Soc. 74, 1805 (1952) h) B. D. Sharma and J. F. McConnell, Acta Crystallogr. 19, 797 (1965) J. Smets, L. Adamowicz and Guido Maes, J. Mol. Struct. 322, 113 (1994).
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    • Sharma, B.D.1    McConnell, J.F.2
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    • 0343185563 scopus 로고
    • For experimental studies on the tautomerism of 4-pyrimidinone see: a) D. J. Brown and L. N. Short, J. Chem. Soc. 331 (1953) b) D. J. Brown, E. Hoerger and S. F. Mason, J. Chem. Soc. 211 (1955) c) A. Albert and E. Spinner, J. Chem. Soc. 1221 (1960) d) Y. Inoue, N. Furutachi and K. Nakanishi, J. Org. Chem. 31, 175 (1966) e) M. J. Nowak and K. Szczepaniak, J. Mol. Struct. 62, 47 (1980) f) L. Lapinski, J. Fulara and M. J. Nowak, Spectrochimica Acta 46A, 61 (1990); For experimental studies on the tautomerism of isocytosine see: g) M. M. Stimson and M. J. O'Donnell, J. Am. Chem. Soc. 74, 1805 (1952) h) B. D. Sharma and J. F. McConnell, Acta Crystallogr. 19, 797 (1965) J. Smets, L. Adamowicz and Guido Maes, J. Mol. Struct. 322, 113 (1994).
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    • note
    • Preliminary theoretical calculations in the gas phase, performed at semiempirical (MNDO and PM3) level, predict consistently for compounds 1, 2 and 3, the enol tautomer to be of highest stability, while among the keto tautomers, the N3 form is calculated as more stable vs. the N1 form by ca. 10 kcal/mol. However, it is known that semiempirical methods are not suited for studies of the relative stability of tautomers and more advanced ab initio quantum mechanical calculations are desired for accurate predictions.
  • 42
    • 2742544797 scopus 로고    scopus 로고
    • note
    • 3 irradiation of the 6-methyl is meaningless in terms of the NOE effect on the NH, due to concomitant saturation transfer to the water peak.
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    • For several reviews and recent papers on the tautomerism of 4-pyrimidinones see: a) J. S. Kwiatkowski, T. J. Zielinski and R. Rei, Adv. Quantum Chem. 18, 85 (1980) b) D. Shugar and K. Szczepaniak, Int. J. Quantum Chem. 20, 573 (1981) c) R. Czerminski, K. Kuczera, H. Rostkowska, M. J. Nowak and K. Szczepaniak, J. Mol. Struct. 140, 235 (1986) d) P. Cieplak, P. Bash, U. C. Singh and P. A. Kollman, J. Am. Chem. Soc. 109, 6283 (1987) e) A. Les, and L. Adamowicz, J. Phys. Chem. 94, 7021 (1990).
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    • Kwiatkowski, J.S.1    Zielinski, T.J.2    Rei, R.3
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    • For several reviews and recent papers on the tautomerism of 4-pyrimidinones see: a) J. S. Kwiatkowski, T. J. Zielinski and R. Rei, Adv. Quantum Chem. 18, 85 (1980) b) D. Shugar and K. Szczepaniak, Int. J. Quantum Chem. 20, 573 (1981) c) R. Czerminski, K. Kuczera, H. Rostkowska, M. J. Nowak and K. Szczepaniak, J. Mol. Struct. 140, 235 (1986) d) P. Cieplak, P. Bash, U. C. Singh and P. A. Kollman, J. Am. Chem. Soc. 109, 6283 (1987) e) A. Les, and L. Adamowicz, J. Phys. Chem. 94, 7021 (1990).
    • (1981) Int. J. Quantum Chem. , vol.20 , pp. 573
    • Shugar, D.1    Szczepaniak, K.2
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    • 0003605835 scopus 로고
    • For several reviews and recent papers on the tautomerism of 4-pyrimidinones see: a) J. S. Kwiatkowski, T. J. Zielinski and R. Rei, Adv. Quantum Chem. 18, 85 (1980) b) D. Shugar and K. Szczepaniak, Int. J. Quantum Chem. 20, 573 (1981) c) R. Czerminski, K. Kuczera, H. Rostkowska, M. J. Nowak and K. Szczepaniak, J. Mol. Struct. 140, 235 (1986) d) P. Cieplak, P. Bash, U. C. Singh and P. A. Kollman, J. Am. Chem. Soc. 109, 6283 (1987) e) A. Les, and L. Adamowicz, J. Phys. Chem. 94, 7021 (1990).
    • (1986) J. Mol. Struct. , vol.140 , pp. 235
    • Czerminski, R.1    Kuczera, K.2    Rostkowska, H.3    Nowak, M.J.4    Szczepaniak, K.5
  • 57
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    • For several reviews and recent papers on the tautomerism of 4-pyrimidinones see: a) J. S. Kwiatkowski, T. J. Zielinski and R. Rei, Adv. Quantum Chem. 18, 85 (1980) b) D. Shugar and K. Szczepaniak, Int. J. Quantum Chem. 20, 573 (1981) c) R. Czerminski, K. Kuczera, H. Rostkowska, M. J. Nowak and K. Szczepaniak, J. Mol. Struct. 140, 235 (1986) d) P. Cieplak, P. Bash, U. C. Singh and P. A. Kollman, J. Am. Chem. Soc. 109, 6283 (1987) e) A. Les, and L. Adamowicz, J. Phys. Chem. 94, 7021 (1990).
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    • Cieplak, P.1    Bash, P.2    Singh, U.C.3    Kollman, P.A.4
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    • For several reviews and recent papers on the tautomerism of 4-pyrimidinones see: a) J. S. Kwiatkowski, T. J. Zielinski and R. Rei, Adv. Quantum Chem. 18, 85 (1980) b) D. Shugar and K. Szczepaniak, Int. J. Quantum Chem. 20, 573 (1981) c) R. Czerminski, K. Kuczera, H. Rostkowska, M. J. Nowak and K. Szczepaniak, J. Mol. Struct. 140, 235 (1986) d) P. Cieplak, P. Bash, U. C. Singh and P. A. Kollman, J. Am. Chem. Soc. 109, 6283 (1987) e) A. Les, and L. Adamowicz, J. Phys. Chem. 94, 7021 (1990).
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    • Les, A.1    Adamowicz, L.2


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