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Volumn 68, Issue 16, 2003, Pages 6172-6183

Model studies toward the synthesis of dihydropyrimidinyl and pyridyl α-amino acids via three-component Biginelli and Hantzsch cyclocondensations

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOCONDENSATION;

EID: 0043032892     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0342830     Document Type: Article
Times cited : (131)

References (62)
  • 1
    • 0038795772 scopus 로고    scopus 로고
    • Asymmetric synthesis of novel sterically constrained amino acids; symposium
    • (a) Hruby, V. J., Soloshonok, V. A., Eds. Asymmetric Synthesis of Novel Sterically Constrained Amino Acids; Symposium. Tetrahedron 2001, 57, 6329-6650.
    • (2001) Tetrahedron , vol.57 , pp. 6329-6650
    • Hruby, V.J.1    Soloshonok, V.A.2
  • 3
    • 0003670259 scopus 로고    scopus 로고
    • Fenniri, H., Ed.; Oxford University Press: Oxford, U.K.
    • (c) Combinatorial Chemistry: A Practical Approach; Fenniri, H., Ed.; Oxford University Press: Oxford, U.K., 2000.
    • (2000) Combinatorial Chemistry: A Practical Approach
  • 26
    • 0037136116 scopus 로고    scopus 로고
    • Amidocarbonylation, Passerini, Ugi, and Petasis multicomponent reactions have been used for the synthesis of different classes of amino acid derivatives: (a) Koolmeister, T.; Södergren, M.; Scobie, M. Tetrahedron Lett. 2002, 43, 5969. (b) Owens, T. D.; Semple, E. Org. Lett. 2001, 21, 3301. (c) Beller, M.; Eckert, M. Angew. Chem., Int. Ed. 2000, 39, 1010. (d) Linderman, R. J.; Binet, S.; Petrich, S. R. J. Org. Chem. 1999, 64, 336. (e) Diker, G. Angew. Chem., Int. Ed. Engl. 1997, 36, 1700.
    • (2002) Tetrahedron Lett. , vol.43 , pp. 5969
    • Koolmeister, T.1    Södergren, M.2    Scobie, M.3
  • 27
    • 0035909598 scopus 로고    scopus 로고
    • Amidocarbonylation, Passerini, Ugi, and Petasis multicomponent reactions have been used for the synthesis of different classes of amino acid derivatives: (a) Koolmeister, T.; Södergren, M.; Scobie, M. Tetrahedron Lett. 2002, 43, 5969. (b) Owens, T. D.; Semple, E. Org. Lett. 2001, 21, 3301. (c) Beller, M.; Eckert, M. Angew. Chem., Int. Ed. 2000, 39, 1010. (d) Linderman, R. J.; Binet, S.; Petrich, S. R. J. Org. Chem. 1999, 64, 336. (e) Diker, G. Angew. Chem., Int. Ed. Engl. 1997, 36, 1700.
    • (2001) Org. Lett. , vol.21 , pp. 3301
    • Owens, T.D.1    Semple, E.2
  • 28
    • 0034677864 scopus 로고    scopus 로고
    • Amidocarbonylation, Passerini, Ugi, and Petasis multicomponent reactions have been used for the synthesis of different classes of amino acid derivatives: (a) Koolmeister, T.; Södergren, M.; Scobie, M. Tetrahedron Lett. 2002, 43, 5969. (b) Owens, T. D.; Semple, E. Org. Lett. 2001, 21, 3301. (c) Beller, M.; Eckert, M. Angew. Chem., Int. Ed. 2000, 39, 1010. (d) Linderman, R. J.; Binet, S.; Petrich, S. R. J. Org. Chem. 1999, 64, 336. (e) Diker, G. Angew. Chem., Int. Ed. Engl. 1997, 36, 1700.
    • (2000) Angew. Chem., Int. Ed. , vol.39 , pp. 1010
    • Beller, M.1    Eckert, M.2
  • 29
    • 0033593261 scopus 로고    scopus 로고
    • Amidocarbonylation, Passerini, Ugi, and Petasis multicomponent reactions have been used for the synthesis of different classes of amino acid derivatives: (a) Koolmeister, T.; Södergren, M.; Scobie, M. Tetrahedron Lett. 2002, 43, 5969. (b) Owens, T. D.; Semple, E. Org. Lett. 2001, 21, 3301. (c) Beller, M.; Eckert, M. Angew. Chem., Int. Ed. 2000, 39, 1010. (d) Linderman, R. J.; Binet, S.; Petrich, S. R. J. Org. Chem. 1999, 64, 336. (e) Diker, G. Angew. Chem., Int. Ed. Engl. 1997, 36, 1700.
    • (1999) J. Org. Chem. , vol.64 , pp. 336
    • Linderman, R.J.1    Binet, S.2    Petrich, S.R.3
  • 30
    • 0030821811 scopus 로고    scopus 로고
    • Amidocarbonylation, Passerini, Ugi, and Petasis multicomponent reactions have been used for the synthesis of different classes of amino acid derivatives: (a) Koolmeister, T.; Södergren, M.; Scobie, M. Tetrahedron Lett. 2002, 43, 5969. (b) Owens, T. D.; Semple, E. Org. Lett. 2001, 21, 3301. (c) Beller, M.; Eckert, M. Angew. Chem., Int. Ed. 2000, 39, 1010. (d) Linderman, R. J.; Binet, S.; Petrich, S. R. J. Org. Chem. 1999, 64, 336. (e) Diker, G. Angew. Chem., Int. Ed. Engl. 1997, 36, 1700.
    • (1997) Angew. Chem., Int. Ed. Engl. , vol.36 , pp. 1700
    • Diker, G.1
  • 31
    • 0037182202 scopus 로고    scopus 로고
    • N-Protected α-amino aldehydes have been used in Passerini reactions: (a) Banfi, L.; Guanti, G.; Riva, R.; Basso, A.; Calcagno, E. Tetrahedron Lett. 2002, 43, 4067. (b) Owens, T. D.; Araldi, G. L.; Nutt, R. F.; Semple, E. Tetrahedron Lett. 2001, 42, 6271.
    • (2002) Tetrahedron Lett. , vol.43 , pp. 4067
    • Banfi, L.1    Guanti, G.2    Riva, R.3    Basso, A.4    Calcagno, E.5
  • 32
    • 0035801852 scopus 로고    scopus 로고
    • N-Protected α-amino aldehydes have been used in Passerini reactions: (a) Banfi, L.; Guanti, G.; Riva, R.; Basso, A.; Calcagno, E. Tetrahedron Lett. 2002, 43, 4067. (b) Owens, T. D.; Araldi, G. L.; Nutt, R. F.; Semple, E. Tetrahedron Lett. 2001, 42, 6271.
    • (2001) Tetrahedron Lett. , vol.42 , pp. 6271
    • Owens, T.D.1    Araldi, G.L.2    Nutt, R.F.3    Semple, E.4
  • 48
    • 0042286502 scopus 로고    scopus 로고
    • note
    • Conversion to amino acids 8 in two steps involving the formation of the corresponding amino aldehydes as intermediates (Swern oxidation then TEMPO-BAIB) disappointingly gave decomposed products.
  • 49
    • 0027205552 scopus 로고
    • The oxidation of DHPM and dihydropyridine (DHP) derivatives is an issue that has been addressed by several authors. Dealkylation (in addition to aromatization) usually occurs when the DHPM and DHP rings bear a secondary alkyl group at the C4 position while dehydrogenation takes place in the presence of a primary alkyl group at the same position. This is a general trend in the oxidation of DHPMs and DHPs and it is explained by a sequence proceeding by a hydride abstraction in the first step. (a) Kappe, C. O. Tetrahedron 1993, 49, 6937. (b) Slavinskaya, V. A.; Duburs, G.; Sile, D.; Kreile, D.; Khanina, E. L. USSR Patent 632,695, 1978. (c) Eynde, J. J. V.; Mayence, A.; Maquestiau, A. Tetrahedron 1992, 3, 463. (d) Böcker, R. H.; Guengerich F. P. J. Med. Chem. 1986, 29, 1596.
    • (1993) Tetrahedron , vol.49 , pp. 6937
    • Kappe, C.O.1
  • 50
    • 0042787592 scopus 로고    scopus 로고
    • USSR Patent 632,695, 1978
    • The oxidation of DHPM and dihydropyridine (DHP) derivatives is an issue that has been addressed by several authors. Dealkylation (in addition to aromatization) usually occurs when the DHPM and DHP rings bear a secondary alkyl group at the C4 position while dehydrogenation takes place in the presence of a primary alkyl group at the same position. This is a general trend in the oxidation of DHPMs and DHPs and it is explained by a sequence proceeding by a hydride abstraction in the first step. (a) Kappe, C. O. Tetrahedron 1993, 49, 6937. (b) Slavinskaya, V. A.; Duburs, G.; Sile, D.; Kreile, D.; Khanina, E. L. USSR Patent 632,695, 1978. (c) Eynde, J. J. V.; Mayence, A.; Maquestiau, A. Tetrahedron 1992, 3, 463. (d) Böcker, R. H.; Guengerich F. P. J. Med. Chem. 1986, 29, 1596.
    • Slavinskaya, V.A.1    Duburs, G.2    Sile, D.3    Kreile, D.4    Khanina, E.L.5
  • 51
    • 0026530628 scopus 로고
    • The oxidation of DHPM and dihydropyridine (DHP) derivatives is an issue that has been addressed by several authors. Dealkylation (in addition to aromatization) usually occurs when the DHPM and DHP rings bear a secondary alkyl group at the C4 position while dehydrogenation takes place in the presence of a primary alkyl group at the same position. This is a general trend in the oxidation of DHPMs and DHPs and it is explained by a sequence proceeding by a hydride abstraction in the first step. (a) Kappe, C. O. Tetrahedron 1993, 49, 6937. (b) Slavinskaya, V. A.; Duburs, G.; Sile, D.; Kreile, D.; Khanina, E. L. USSR Patent 632,695, 1978. (c) Eynde, J. J. V.; Mayence, A.; Maquestiau, A. Tetrahedron 1992, 3, 463. (d) Böcker, R. H.; Guengerich F. P. J. Med. Chem. 1986, 29, 1596.
    • (1992) Tetrahedron , vol.3 , pp. 463
    • Eynde, J.J.V.1    Mayence, A.2    Maquestiau, A.3
  • 52
    • 0022550688 scopus 로고
    • The oxidation of DHPM and dihydropyridine (DHP) derivatives is an issue that has been addressed by several authors. Dealkylation (in addition to aromatization) usually occurs when the DHPM and DHP rings bear a secondary alkyl group at the C4 position while dehydrogenation takes place in the presence of a primary alkyl group at the same position. This is a general trend in the oxidation of DHPMs and DHPs and it is explained by a sequence proceeding by a hydride abstraction in the first step. (a) Kappe, C. O. Tetrahedron 1993, 49, 6937. (b) Slavinskaya, V. A.; Duburs, G.; Sile, D.; Kreile, D.; Khanina, E. L. USSR Patent 632,695, 1978. (c) Eynde, J. J. V.; Mayence, A.; Maquestiau, A. Tetrahedron 1992, 3, 463. (d) Böcker, R. H.; Guengerich F. P. J. Med. Chem. 1986, 29, 1596.
    • (1986) J. Med. Chem. , vol.29 , pp. 1596
    • Böcker, R.H.1    Guengerich, F.P.2
  • 53
    • 0042286501 scopus 로고    scopus 로고
    • note
    • Each step occurred in fair yield (benzylation, 65%; hydrolysis, 50%) but after column chromatography it was possible to recover monobenzylated (benzylation step) and dibenzylated (hydrolysis step) derivatives of 4 that were reused in appropriate reactions of Scheme 1.
  • 54
    • 0043288667 scopus 로고    scopus 로고
    • note
    • One-step oxidative cleavage of the oxazolidine ring with the Jones reagent (see ref 14a,b) afforded the corresponding amino acid in lower overall yield.
  • 55
    • 0043288663 scopus 로고    scopus 로고
    • note
    • A different protection strategy based on selective N3 acylation (acetyl and pivaloyl groups) of cycloadducts 4 was also investigated to allow a higher yielding deprotection to 8. Unfortunately, N,O-acyl migration occurred during acetonide removal of N-acyl cycloadducts affording undesired O-acyl derivatives of 5.
  • 58
    • 0041785447 scopus 로고    scopus 로고
    • note
    • The use of the Jones reagent gave a lower yield (ca. 50%) of N′-Boc amino acid 29.
  • 61
    • 0004150157 scopus 로고    scopus 로고
    • Program for the Refinement for Crystal Structures; University of: Göttingen, Germany
    • Sheldrick, G. M. SHELXL-97, Program for the Refinement for Crystal Structures; University of Göttingen: Göttingen, Germany, 1997.
    • (1997) SHELXL-97
    • Sheldrick, G.M.1
  • 62
    • 0004271269 scopus 로고    scopus 로고
    • Oak Ridge National Laboratory: Oak Ridge, TN; Report ORNL-6895
    • Burnett, M. N.; Johnson, C. K. ORTEP III; Oak Ridge National Laboratory: Oak Ridge, TN, 1996; Report ORNL-6895.
    • (1996) ORTEP III
    • Burnett, M.N.1    Johnson, C.K.2


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