Intramolecular [2+2] cycloaddition of ketenimines with imines

Tetrahedron Letters

Volumn 37, Issue 49, 1996, Pages 8945-8948

  Alajarín, Mateo ^a   Molina, Pedro ^a   Vidal, Angel ^a  

^a UNIVERSITY OF MURCIA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

AZETIDINE DERIVATIVE; QUINAZOLINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; INFRARED SPECTROPHOTOMETRY; REACTION ANALYSIS;

EID: 0030566859     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02054-0     Document Type: Article

References (33)

1. 1. Staudinger, H.; Hauser, E. Helv. Chim. Acta 1921, 4, 887.
2. 2. a) Barker M, W.; McHenry, W. E. in The Chemistry of Ketenes, Allenes, and Related Compounds, Patai, S., Ed.; Wiley-Interscience: Chichester, England, 1980; Part 2, pp. 701-720;
3. b) Gambaryan, N. P. Russ. Chem. Rev. (Engl. Transl.) 1976, 45, 630; Usp. Khim. 1976, 45, 1251;
4. b) Gambaryan, N. P. Russ. Chem. Rev. (Engl. Transl.) 1976, 45, 630; Usp. Khim. 1976, 45, 1251;
5. c) Krow, G. R. Angew. Chem. Int. Ed. Engl. 1971, 10, 435.
6. 3. Aumann, R. Chem. Ber. 1993, 126, 1867; Merlic, C. A.; Burns, E. E. Tetrahedron Lett. 1993, 34, 5401 and references cited therein.
7. 3. Aumann, R. Chem. Ber. 1993, 126, 1867; Merlic, C. A.; Burns, E. E. Tetrahedron Lett. 1993, 34, 5401 and references cited therein.
8. 4. a) Walters, M. A. J. Am. Chem. Soc. 1994, 116, 11618;
9. b) Walters, M. A.; Hoem, A. B. J. Org. Chem. 1994, 59, 2645;
10. c) Molina, P.; Alajarín, M.; López-Leonardo, C.; Alcántara, J. Tetrahedron 1993,49, 5153;
11. d) Bruckner, R.; Huisgen, R. Tetrahedron Lett. 1994, 35, 3281;
12. e) Molina, P.; Alajarín, M.; López-Leonardo, C. Tetrahedron Lett. 1991, 32, 4041;
13. f) Walters, M. A.; McDonough, C. S.; Brown, P. S., Jr.; Hoem, A. B. Tetrahedron Lett. 1991, 32, 179.
14. 5. Ghosez, L.; Bogdan, S.; Ceresiat, M.; Frydrych, C.; Marchand-Brynaert, J.; Moya-Portuguez, M.; Huber, I. Pure Appl Chem. 1987, 59, 393.
15. 6. For reviews on [2 + 2] cycloaddition reactions of ketenimines see: a) Ghosez, L.; Marchand-Brynaert, J. in Comprehensive Organic Synthesis, Trost, B. M.; Fleming, I.; Eds. Pergamon Press: Oxford, U. K. 1991; Vol. 5, pp. 108-114;
16. b) Dondoni, A. Heterocycles 1980, 14, 1567.
17. 7. Van Camp, A.; Gossens, D.; Moya-Portuguez, M.; Marchand-Brynaert, J.; Ghosez, L. Tetrahedron Lett. 1980, 21, 3081.
18. 8. Arnold, B.; Regitz, M. Angew. Chem. Int. Ed. Engl. 1979, 18, 320.
19. 5-phosphazenes.
20. 10. Molina, P.; Alajarín, M.; Vidal, A.; Foces-Foces, C. Tetrahedron 1995, 51, 12127; Molina, P.; Alajarín, M.; Vidal, A. J. Org. Chem. 1992, 57, 6703; Molina, P.; Alajarín, M.; Vidal, A.; Fenau-Dupont, J.; Declerq, J. P. J. Org. Chem. 1991, 56, 4008; Molina, P.; Alajarín, M.; Vidal, A. Tetrahedron Lett. 1991, 32, 5379; Molina, P.; Alajarín, M.; Vidal, A.; Fenau-Dupont, J.; Declerq, J. P. J. Chem. Soc. Chem. Commun. 1990, 829.
21. 10. Molina, P.; Alajarín, M.; Vidal, A.; Foces-Foces, C. Tetrahedron 1995, 51, 12127; Molina, P.; Alajarín, M.; Vidal, A. J. Org. Chem. 1992, 57, 6703; Molina, P.; Alajarín, M.; Vidal, A.; Fenau-Dupont, J.; Declerq, J. P. J. Org. Chem. 1991, 56, 4008; Molina, P.; Alajarín, M.; Vidal, A. Tetrahedron Lett. 1991, 32, 5379; Molina, P.; Alajarín, M.; Vidal, A.; Fenau-Dupont, J.; Declerq, J. P. J. Chem. Soc. Chem. Commun. 1990, 829.
22. 10. Molina, P.; Alajarín, M.; Vidal, A.; Foces-Foces, C. Tetrahedron 1995, 51, 12127; Molina, P.; Alajarín, M.; Vidal, A. J. Org. Chem. 1992, 57, 6703; Molina, P.; Alajarín, M.; Vidal, A.; Fenau-Dupont, J.; Declerq, J. P. J. Org. Chem. 1991, 56, 4008; Molina, P.; Alajarín, M.; Vidal, A. Tetrahedron Lett. 1991, 32, 5379; Molina, P.; Alajarín, M.; Vidal, A.; Fenau-Dupont, J.; Declerq, J. P. J. Chem. Soc. Chem. Commun. 1990, 829.
23. 10. Molina, P.; Alajarín, M.; Vidal, A.; Foces-Foces, C. Tetrahedron 1995, 51, 12127; Molina, P.; Alajarín, M.; Vidal, A. J. Org. Chem. 1992, 57, 6703; Molina, P.; Alajarín, M.; Vidal, A.; Fenau-Dupont, J.; Declerq, J. P. J. Org. Chem. 1991, 56, 4008; Molina, P.; Alajarín, M.; Vidal, A. Tetrahedron Lett. 1991, 32, 5379; Molina, P.; Alajarín, M.; Vidal, A.; Fenau-Dupont, J.; Declerq, J. P. J. Chem. Soc. Chem. Commun. 1990, 829.
24. 10. Molina, P.; Alajarín, M.; Vidal, A.; Foces-Foces, C. Tetrahedron 1995, 51, 12127; Molina, P.; Alajarín, M.; Vidal, A. J. Org. Chem. 1992, 57, 6703; Molina, P.; Alajarín, M.; Vidal, A.; Fenau-Dupont, J.; Declerq, J. P. J. Org. Chem. 1991, 56, 4008; Molina, P.; Alajarín, M.; Vidal, A. Tetrahedron Lett. 1991, 32, 5379; Molina, P.; Alajarín, M.; Vidal, A.; Fenau-Dupont, J.; Declerq, J. P. J. Chem. Soc. Chem. Commun. 1990, 829.
25. 11. Smith, P. A. S.; Budde, G. F.; Shang-Shing, P. C. J. Org. Chem. 1985, 50, 2062.
26. 12. Morris, K. G.; Thomas, S. E. J. Chem.. Soc. Perkin Trans. 1 1991, 97; Texier-Boullet, F. Synthesis 1985, 679.
27. 12. Morris, K. G.; Thomas, S. E. J. Chem.. Soc. Perkin Trans. 1 1991, 97; Texier-Boullet, F. Synthesis 1985, 679.
28. 13C-NMR, mass spectra and elemental analyses were obtained for all new compounds.
29. 14. Imines 5 were used as crude products in the next step, due to the partial hydrolytic cleavage of the imino bond experienced by some of them during purification attempts by crystallization or column chromatography.
30. 4) is in accordance with the proposed E configuration: Fraser, R. R.; Banville, J.; Akiyama, F.; Chuaqui-Offermanns, N. Can. J. Chem. 1981, 59, 705.
31. 16. Taylor, E. C; McKillop, A.; Hawks, G. H. Org. Synth. 1973, 52, 36.
32. 17. For a recent review see: Molina, P.; Vilaplana, M. J. Synthesis 1994, 1197.
33. + 76), 165 (100).