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Volumn 62, Issue 21, 1997, Pages 7201-7204

A reexamination of the mechanism of the Biginelli dihydropyrimidine synthesis. Support for an N-acyliminium ion intermediate

Author keywords

[No Author keywords available]

Indexed keywords

1,2,3,4 TETRAHYDROPYRIMIDINE DERIVATIVE; ACETOACETIC ACID DERIVATIVE; BENZALDEHYDE; IMINE; METHYLUREA; PYRIMIDINE DERIVATIVE;

EID: 0030732273     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo971010u     Document Type: Article
Times cited : (511)

References (44)
  • 3
    • 0027205552 scopus 로고
    • For a review of the Biginelli-condensation, see: Kappe, C. O. Tetrahedron 1993, 49, 6937-6963.
    • (1993) Tetrahedron , vol.49 , pp. 6937-6963
    • Kappe, C.O.1
  • 4
    • 0030983617 scopus 로고    scopus 로고
    • Kappe, C. O.; Peters. K.; Peters, E.-M. J. Org. Chem. 1997, 62, 2786-2797. Kappe, C. O.; Fabian, W. M. F.; Semones, M. A. Tetrahedron 1997, 53, 2803-2816.
    • (1997) J. Org. Chem. , vol.62 , pp. 2786-2797
    • Kappe, C.O.1    Peters, K.2    Peters, E.-M.3
  • 5
    • 0031584880 scopus 로고    scopus 로고
    • Kappe, C. O.; Peters. K.; Peters, E.-M. J. Org. Chem. 1997, 62, 2786-2797. Kappe, C. O.; Fabian, W. M. F.; Semones, M. A. Tetrahedron 1997, 53, 2803-2816.
    • (1997) Tetrahedron , vol.53 , pp. 2803-2816
    • Kappe, C.O.1    Fabian, W.M.F.2    Semones, M.A.3
  • 6
    • 0001235198 scopus 로고
    • O'Reilly, B. C.; Atwal, K. S. Heterocycles 1987, 26, 1185-1188. Atwal, K. S.; Rovnyak, G. C.; O'Reilly, B. C.; Schwartz, J. J. Org. Chem. 1989, 54, 5898-5907. Gupta, R.; Gupta, A. K.; Paul, S.; Kachroo, P. L. Ind. J. Chem. 1995, 34B, 151-152. Sár, C. P.; Hankovszky, O. H.; Jerkovich, G.; Pallagi, I.; Hideg, K. ACH-Models Chem. 1994, 131, 363-376.
    • (1987) Heterocycles , vol.26 , pp. 1185-1188
    • O'Reilly, B.C.1    Atwal, K.S.2
  • 7
    • 0024818583 scopus 로고
    • O'Reilly, B. C.; Atwal, K. S. Heterocycles 1987, 26, 1185-1188. Atwal, K. S.; Rovnyak, G. C.; O'Reilly, B. C.; Schwartz, J. J. Org. Chem. 1989, 54, 5898-5907. Gupta, R.; Gupta, A. K.; Paul, S.; Kachroo, P. L. Ind. J. Chem. 1995, 34B, 151-152. Sár, C. P.; Hankovszky, O. H.; Jerkovich, G.; Pallagi, I.; Hideg, K. ACH-Models Chem. 1994, 131, 363-376.
    • (1989) J. Org. Chem. , vol.54 , pp. 5898-5907
    • Atwal, K.S.1    Rovnyak, G.C.2    O'Reilly, B.C.3    Schwartz, J.4
  • 8
    • 0003138062 scopus 로고
    • O'Reilly, B. C.; Atwal, K. S. Heterocycles 1987, 26, 1185-1188. Atwal, K. S.; Rovnyak, G. C.; O'Reilly, B. C.; Schwartz, J. J. Org. Chem. 1989, 54, 5898-5907. Gupta, R.; Gupta, A. K.; Paul, S.; Kachroo, P. L. Ind. J. Chem. 1995, 34B, 151-152. Sár, C. P.; Hankovszky, O. H.; Jerkovich, G.; Pallagi, I.; Hideg, K. ACH-Models Chem. 1994, 131, 363-376.
    • (1995) Ind. J. Chem. , vol.34 B , pp. 151-152
    • Gupta, R.1    Gupta, A.K.2    Paul, S.3    Kachroo, P.L.4
  • 9
    • 0004907286 scopus 로고
    • O'Reilly, B. C.; Atwal, K. S. Heterocycles 1987, 26, 1185-1188. Atwal, K. S.; Rovnyak, G. C.; O'Reilly, B. C.; Schwartz, J. J. Org. Chem. 1989, 54, 5898-5907. Gupta, R.; Gupta, A. K.; Paul, S.; Kachroo, P. L. Ind. J. Chem. 1995, 34B, 151-152. Sár, C. P.; Hankovszky, O. H.; Jerkovich, G.; Pallagi, I.; Hideg, K. ACH-Models Chem. 1994, 131, 363-376.
    • (1994) ACH-Models Chem. , vol.131 , pp. 363-376
    • Sár, C.P.1    Hankovszky, O.H.2    Jerkovich, G.3    Pallagi, I.4    Hideg, K.5
  • 10
    • 0028827034 scopus 로고    scopus 로고
    • Wipf, P.; Cunningham, A. Tetrahedron Lett. 1995, 36, 7819-7822. Studer, A.; Jeger, P.; Wipf, P.; Curran, D. P. J. Org. Chem. 1997, 62, 2917-2924. Robinett, L. D.; Yager, K. M.; Phelan, J. C. 211th National Meeting of the American Chemical Society, New Orleans, 1996; American Chemical Society: Washington, DC, 1996; ORGN 122.
    • (1995) Tetrahedron Lett. , vol.36 , pp. 7819-7822
    • Wipf, P.1    Cunningham, A.2
  • 11
    • 0001591221 scopus 로고    scopus 로고
    • Wipf, P.; Cunningham, A. Tetrahedron Lett. 1995, 36, 7819-7822. Studer, A.; Jeger, P.; Wipf, P.; Curran, D. P. J. Org. Chem. 1997, 62, 2917-2924. Robinett, L. D.; Yager, K. M.; Phelan, J. C. 211th National Meeting of the American Chemical Society, New Orleans, 1996; American Chemical Society: Washington, DC, 1996; ORGN 122.
    • (1997) J. Org. Chem. , vol.62 , pp. 2917-2924
    • Studer, A.1    Jeger, P.2    Wipf, P.3    Curran, D.P.4
  • 12
    • 0028827034 scopus 로고    scopus 로고
    • New Orleans, American Chemical Society: Washington, DC, 1996; ORGN 122
    • Wipf, P.; Cunningham, A. Tetrahedron Lett. 1995, 36, 7819-7822. Studer, A.; Jeger, P.; Wipf, P.; Curran, D. P. J. Org. Chem. 1997, 62, 2917-2924. Robinett, L. D.; Yager, K. M.; Phelan, J. C. 211th National Meeting of the American Chemical Society, New Orleans, 1996; American Chemical Society: Washington, DC, 1996; ORGN 122.
    • (1996) 211th National Meeting of the American Chemical Society
    • Robinett, L.D.1    Yager, K.M.2    Phelan, J.C.3
  • 16
    • 33751385241 scopus 로고
    • and references therein
    • Snider, B. B.; Shi, Z. J. Org. Chem. 1993, 58, 3828-3839, and references therein.
    • (1993) J. Org. Chem. , vol.58 , pp. 3828-3839
    • Snider, B.B.1    Shi, Z.2
  • 20
    • 0000685535 scopus 로고
    • Overman, L. E.; Rabinowitz, M. H. J. Org. Chem. 1993, 58, 3235-3237. Overman, L. E.; Rabinowitz, M. H.; Renhowe, P. A. J. Am. Chem. Soc. 1995, 117, 2657-2658.
    • (1993) J. Org. Chem. , vol.58 , pp. 3235-3237
    • Overman, L.E.1    Rabinowitz, M.H.2
  • 25
    • 9844253489 scopus 로고    scopus 로고
    • note
    • 18
  • 27
    • 0000851696 scopus 로고
    • Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford
    • Heathcock, C. H. Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford; 1991; Vol. 2, p 133-179. Nielson, A. T.; Houlihan, W. Org. React. (N.Y.) 1968, 16, 1-438.
    • (1991) Comprehensive Organic Synthesis , vol.2 , pp. 133-179
    • Heathcock, C.H.1
  • 28
    • 0008926115 scopus 로고
    • Heathcock, C. H. Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford; 1991; Vol. 2, p 133-179. Nielson, A. T.; Houlihan, W. Org. React. (N.Y.) 1968, 16, 1-438.
    • (1968) Org. React. (N.Y.) , vol.16 , pp. 1-438
    • Nielson, A.T.1    Houlihan, W.2
  • 30
    • 0001235201 scopus 로고
    • For an analogous cyclocondensation using N-benzylthiourea, the structure of the thiazine product was confirmed by X-ray analysis: Atwal, K S.; O'Reilley, B. C.; Gougoutas, J. Z.; Malley, M. F. Heterocycles 1987, 26, 1189-1192.
    • (1987) Heterocycles , vol.26 , pp. 1189-1192
    • Atwal, K.S.1    O'Reilley, B.C.2    Gougoutas, J.Z.3    Malley, M.F.4
  • 32
    • 85007883878 scopus 로고
    • Senda, S.; Suzui, A. Chem. Pharm. Bull. 1958, 6, 476-479. Hlousek, J.; Machacek, V.; Sterba, V. Sb. Ved. Pr., Vys. Sk. Chemickotecknol. Pardubice 1978, 39, 11-25 (Chem. Abstr. 1979, 91, 174663n).
    • (1958) Chem. Pharm. Bull. , vol.6 , pp. 476-479
    • Senda, S.1    Suzui, A.2
  • 34
    • 85007883878 scopus 로고
    • Senda, S.; Suzui, A. Chem. Pharm. Bull. 1958, 6, 476-479. Hlousek, J.; Machacek, V.; Sterba, V. Sb. Ved. Pr., Vys. Sk. Chemickotecknol. Pardubice 1978, 39, 11-25 (Chem. Abstr. 1979, 91, 174663n).
    • (1979) Chem. Abstr. , vol.91
  • 35
    • 84920442952 scopus 로고
    • Schiff, H. Ann. 1869, 151, 186-213. Lüdy, E. Monatsh. Chem. 1889, 10, 295-316. Bakibaev, A. A.; Tignibidina, L. G.; Filimonov, V. D.; Gorshkova, V. K.; Saratikov, A. S. Khim. Farm. Zh. 1991, 25, 31-35. Bakibaev, A. A. Zh. Org. Khim. 1994, 11, 1686-1687.
    • (1869) Ann. , vol.151 , pp. 186-213
    • Schiff, H.1
  • 36
    • 9844251915 scopus 로고
    • Schiff, H. Ann. 1869, 151, 186-213. Lüdy, E. Monatsh. Chem. 1889, 10, 295-316. Bakibaev, A. A.; Tignibidina, L. G.; Filimonov, V. D.; Gorshkova, V. K.; Saratikov, A. S. Khim. Farm. Zh. 1991, 25, 31-35. Bakibaev, A. A. Zh. Org. Khim. 1994, 11, 1686-1687.
    • (1889) Monatsh. Chem. , vol.10 , pp. 295-316
    • Lüdy, E.1
  • 38
    • 9844252500 scopus 로고
    • Schiff, H. Ann. 1869, 151, 186-213. Lüdy, E. Monatsh. Chem. 1889, 10, 295-316. Bakibaev, A. A.; Tignibidina, L. G.; Filimonov, V. D.; Gorshkova, V. K.; Saratikov, A. S. Khim. Farm. Zh. 1991, 25, 31-35. Bakibaev, A. A. Zh. Org. Khim. 1994, 11, 1686-1687.
    • (1994) Zh. Org. Khim. , vol.11 , pp. 1686-1687
    • Bakibaev, A.A.1
  • 39
    • 84933837089 scopus 로고
    • Schiff, H. Ann. 1896, 291, 367-377. See also Koyano, K.; McArthur, C. R. Can. J. Chem. 1973, 51, 333-337.
    • (1896) Ann. , vol.291 , pp. 367-377
    • Schiff, H.1
  • 41
    • 0000997425 scopus 로고
    • Trost, B. M.; Fleming, I.; Eds.; Pergamon Press: Oxford
    • Overman, L. E.; Ricca, D. J. Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I.; Eds.; Pergamon Press: Oxford; Vol. 2, 1991; p 1007-1046. Hiemstra, H.; Speckamp, W. N. Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I.; Eds.; Pergamon Press: Oxford; Vol. 2, 1991; p 1047-1082, and references therein.
    • (1991) Comprehensive Organic Synthesis , vol.2 , pp. 1007-1046
    • Overman, L.E.1    Ricca, D.J.2
  • 42
    • 0001673091 scopus 로고
    • Trost, B. M.; Fleming, I.; Eds.; Pergamon Press: Oxford; and references therein
    • Overman, L. E.; Ricca, D. J. Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I.; Eds.; Pergamon Press: Oxford; Vol. 2, 1991; p 1007-1046. Hiemstra, H.; Speckamp, W. N. Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I.; Eds.; Pergamon Press: Oxford; Vol. 2, 1991; p 1047-1082, and references therein.
    • (1991) Comprehensive Organic Synthesis , vol.2 , pp. 1047-1082
    • Hiemstra, H.1    Speckamp, W.N.2
  • 43
    • 0021258363 scopus 로고    scopus 로고
    • Okamoto, K. T.; Clardy, J. Tetrahedron Lett. 1984, 25, 2937-2940. Dijkink, J.; Deghati, P. Y. F.; Hiemstra, H. 11th IUPAC Conference on Organic Synthesis, Amsterdam, June 30-July 4, 1996, Book of Abstracts p 379.
    • (1984) Tetrahedron Lett. , vol.25 , pp. 2937-2940
    • Okamoto, K.T.1    Clardy, J.2


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