Reactions of N-unsubstituted 4-amino-1-azadienes towards electrophiles

Synthesis

Volumn , Issue 1, 1996, Pages 133-140

  Barluenga, José ^a   Del Pozo, Carlos ^a   Olano, Bernardo ^a  

^a UNIVERSITY OF OVIEDO   (Spain)

Author keywords

2,3 dihydropyrimidines; C alkylation; N unsubstituted 4 amino 1 azadienes; pyrimidines

Indexed keywords

AMINE; PYRIMIDINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0030033595     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-4160     Document Type: Article

References (28)

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5. For general reviews see: Barluenga, J. Bull. Soc. Chim. Belg. 1988, 97, 545. Barluenga, J.; Tomás, M. Adv. Heterocycl. Chem. 1993, 57, 1. For recent articles see: Barluenga, J.; Aguilar, E.; Joglar, J.; Olano, B.; Fustero, S. J. Org. Chem. 1989, 54, 2596. Barluenga, J.; Aguilar, E.; Fustero, S.; Olano, B.; Viado, A. L. J. Org. Chem. 1992, 57, 1219. Barluenga, J.; Viado, A. L.; Aguilar, E.; Fustero, S.; Olano, B. J. Org. Chem. 1993, 58, 5972.
6. For general reviews see: Barluenga, J. Bull. Soc. Chim. Belg. 1988, 97, 545. Barluenga, J.; Tomás, M. Adv. Heterocycl. Chem. 1993, 57, 1. For recent articles see: Barluenga, J.; Aguilar, E.; Joglar, J.; Olano, B.; Fustero, S. J. Org. Chem. 1989, 54, 2596. Barluenga, J.; Aguilar, E.; Fustero, S.; Olano, B.; Viado, A. L. J. Org. Chem. 1992, 57, 1219. Barluenga, J.; Viado, A. L.; Aguilar, E.; Fustero, S.; Olano, B. J. Org. Chem. 1993, 58, 5972.
7. For general reviews see: Barluenga, J. Bull. Soc. Chim. Belg. 1988, 97, 545. Barluenga, J.; Tomás, M. Adv. Heterocycl. Chem. 1993, 57, 1. For recent articles see: Barluenga, J.; Aguilar, E.; Joglar, J.; Olano, B.; Fustero, S. J. Org. Chem. 1989, 54, 2596. Barluenga, J.; Aguilar, E.; Fustero, S.; Olano, B.; Viado, A. L. J. Org. Chem. 1992, 57, 1219. Barluenga, J.; Viado, A. L.; Aguilar, E.; Fustero, S.; Olano, B. J. Org. Chem. 1993, 58, 5972.
8. For general reviews see: Barluenga, J. Bull. Soc. Chim. Belg. 1988, 97, 545. Barluenga, J.; Tomás, M. Adv. Heterocycl. Chem. 1993, 57, 1. For recent articles see: Barluenga, J.; Aguilar, E.; Joglar, J.; Olano, B.; Fustero, S. J. Org. Chem. 1989, 54, 2596. Barluenga, J.; Aguilar, E.; Fustero, S.; Olano, B.; Viado, A. L. J. Org. Chem. 1992, 57, 1219. Barluenga, J.; Viado, A. L.; Aguilar, E.; Fustero, S.; Olano, B. J. Org. Chem. 1993, 58, 5972.
9. For general reviews see: Barluenga, J. Bull. Soc. Chim. Belg. 1988, 97, 545. Barluenga, J.; Tomás, M. Adv. Heterocycl. Chem. 1993, 57, 1. For recent articles see: Barluenga, J.; Aguilar, E.; Joglar, J.; Olano, B.; Fustero, S. J. Org. Chem. 1989, 54, 2596. Barluenga, J.; Aguilar, E.; Fustero, S.; Olano, B.; Viado, A. L. J. Org. Chem. 1992, 57, 1219. Barluenga, J.; Viado, A. L.; Aguilar, E.; Fustero, S.; Olano, B. J. Org. Chem. 1993, 58, 5972.
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17. Attempts to isolate and characterize 3f-h under inert atmosphere and anhydrous conditions were also unsuccessful.
18. Barluenga, J.; Tomás, M.; Ortiz, J. F. L.; Gotor, V. J. Chem. Soc., Perkin Trans. 1 1983, 2273.
19. Barluenga, J.; González, J. M.; Campos, P. J.; Asensio, G. Angew. Chem. 1985, 97, 341; Angew. Chem., Int. Ed. Engl. 1985, 24, 319. Barluenga, J.; González, J. M.; Carcía-Martín, M. A.; Campos, P. J.; Asensio, G. J. Org. Chem. 1993, 58, 2058.
20. Barluenga, J.; González, J. M.; Campos, P. J.; Asensio, G. Angew. Chem. 1985, 97, 341; Angew. Chem., Int. Ed. Engl. 1985, 24, 319. Barluenga, J.; González, J. M.; Carcía-Martín, M. A.; Campos, P. J.; Asensio, G. J. Org. Chem. 1993, 58, 2058.
21. Barluenga, J.; González, J. M.; Campos, P. J.; Asensio, G. Angew. Chem. 1985, 97, 341; Angew. Chem., Int. Ed. Engl. 1985, 24, 319. Barluenga, J.; González, J. M.; Carcía-Martín, M. A.; Campos, P. J.; Asensio, G. J. Org. Chem. 1993, 58, 2058.
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25. 2COCl, unchanged starting material (up to 50%) together with a mixture of 6 and 7 were always obtained. Moreover, when the reaction was carried out with anhydrides instead of acyl chlorides, part of the starting azadiene was recovered.
26. 3N the corresponding pyrimidines 6 formed from the remaining azadienes were obtained.
27. 2 being anti to each other. Viado, A. L. Ph. D. Dissertation, University of Oviedo, Oviedo, 1994.
28. For a review see: Ho, T.-L. Tetrahedron 1985, 41, 1.