Selective N1-alkylation of 3,4-dihydropyrimidin-2(1H)-ones using Mitsunobu-type conditions

Synlett

Volumn , Issue 11, 2002, Pages 1901-1903

  Dallinger, Doris ^a   Kappe, C Oliver ^a  

^a UNIVERSITY OF GRAZ   (Austria)

Author keywords

Amides; Biginelli condensation; Dihydropyrimidones; Mitsunobu reaction; Selective alkylations

Indexed keywords

ALCOHOL DERIVATIVE; AMIDE; PHOSPHINE DERIVATIVE; PYRIMIDINE DERIVATIVE; REAGENT;

ALKYLATION; ARTICLE; MITSUNOBU REACTION; PKA; REACTION ANALYSIS; REACTION TIME; STEREOCHEMISTRY; TEMPERATURE;

EID: 0036428125     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2002-34881     Document Type: Article

References (27)

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18. In general, examples found in the literature are limited to relatively acidic sulfonamides or trifluoroacetamides. For some recent examples involving amides, see: (a) Kozai, S.; Takaoka, S.; Maruyama, T. Tetrahedron Lett. 2002, 43, 2633. (b) Evans, P. A.; Manangan, T. Tetrahedron Lett. 2001, 42, 6637. (c) Bombrun, A.; Casi, G. Tetrahedron Lett. 2002, 43, 2187. (d) Reichwein, J. F.; Liskamp, R. M. J. Tetrahedron Lett. 1998, 39, 1243.
19. In general, examples found in the literature are limited to relatively acidic sulfonamides or trifluoroacetamides. For some recent examples involving amides, see: (a) Kozai, S.; Takaoka, S.; Maruyama, T. Tetrahedron Lett. 2002, 43, 2633. (b) Evans, P. A.; Manangan, T. Tetrahedron Lett. 2001, 42, 6637. (c) Bombrun, A.; Casi, G. Tetrahedron Lett. 2002, 43, 2187. (d) Reichwein, J. F.; Liskamp, R. M. J. Tetrahedron Lett. 1998, 39, 1243.
20. In general, examples found in the literature are limited to relatively acidic sulfonamides or trifluoroacetamides. For some recent examples involving amides, see: (a) Kozai, S.; Takaoka, S.; Maruyama, T. Tetrahedron Lett. 2002, 43, 2633. (b) Evans, P. A.; Manangan, T. Tetrahedron Lett. 2001, 42, 6637. (c) Bombrun, A.; Casi, G. Tetrahedron Lett. 2002, 43, 2187. (d) Reichwein, J. F.; Liskamp, R. M. J. Tetrahedron Lett. 1998, 39, 1243.
21. In general, examples found in the literature are limited to relatively acidic sulfonamides or trifluoroacetamides. For some recent examples involving amides, see: (a) Kozai, S.; Takaoka, S.; Maruyama, T. Tetrahedron Lett. 2002, 43, 2633. (b) Evans, P. A.; Manangan, T. Tetrahedron Lett. 2001, 42, 6637. (c) Bombrun, A.; Casi, G. Tetrahedron Lett. 2002, 43, 2187. (d) Reichwein, J. F.; Liskamp, R. M. J. Tetrahedron Lett. 1998, 39, 1243.
22. Note that the use of high-temperature microwave chemistry was unsuccessful here. For microwave-assisted Mitsunobu alkylations, see: Steinreiber, A.; Stadler, A.; Mayer, S. F.; Faber, K.; Kappe, C. O. Tetrahedron Lett. 2001, 42, 6283.
23. 1H NMR spectroscopy (characteristic 3-5 Hz coupling between C4-H and N3-H) readily allows one to distinguish between N1-, N3- and O-alklyated DHPMs. For details and the selective preparation of N3-alkylated DHPMs, see: Kappe, C. O.; Roschger, P. J. Heterocycl. Chem. 1989, 26, 55.
24. +].
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