Synthesis of aromatic 1,2-diazines by inverse electron demand Diels-Alder reaction of polymer-supported 1,2,4,5-tetrazines

Tetrahedron Letters

Volumn 37, Issue 45, 1996, Pages 8151-8154

  Panek, James S ^a   Zhu, Bin ^a  

^a BOSTON UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PYRIDAZINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; TECHNIQUE;

BETULACEAE;

EID: 0030569267     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01866-7     Document Type: Article

References (15)

1. 1. Reviews: (a) Moos, W. H.; Green, G. D.; Pavia, M. R. Annu. Rep. Med. Chem. 1993, 28, 315-324.
2. (b) Thompsom, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555-600.
3. (c) Hermkens, P. H. H.; Ottenheijm, H. C.; Rees, D. Tetrahedron 1996, 52, 4527-4554.
4. (d) Gallop, M. A.; Barret, R. W.; Dower, W. J.; Fodor, S. P. A.; Gordon, E. M. J. Med. Chem. 1994, 37, 1233-1251.
5. (e) Gordon, E. M.; Barrett, R. W.; Dower, W. J.; Fodor, S. P. A.; Gallop, M. A. J. Med. Chem. 1994, 37, 1385-1401.
6. 2. Reviews: (a) Boger, D. L. Tetrahedron 1983, 39, 2869-2939.
7. (b) Boger, D. L. Chem. Rev. 1986, 86, 781-793.
8. (c) Boger, D. L., Weinreb, S. M. Hetero Diels-Alder Methodology in Organic Synthesis, Academic Press, San Diego, 1987, Chapter 10, pp 300.
9. 3. Boger, D. L.; Sakya, S. M. J. Org. Chem. 1988, 53, 1415-1423.
10. 4. Barlin, G. B.; Brown, W. V. J. Chem. Soc. (C) 1967, 2473-2476.
11. 2 (4.0 equiv) refluxing in dry benzene for 12 h. The resulting resin was washed with dry benzene under argon and dried in vacuo to afford the acid chloride 1 as a light brown colored solid.
12. 2H which is 2.5 mmol/g.
13. 7. Base promoted hydrolysis of 7 without removal of Boc group resulted in the partial loss of Boc group and substitution of the SMe with OMe in the product, thus decreasing the purity of the product.
14. 8. The reaction of tetrazine complex 5 with alkynes produced only trace amounts of cycloaddition products.
15. 3 in 1:2 MeOH-THF for 12 h. The reaction mixture was filtered and the filtrate was extracted with EtOAc and the organic solution was dried to afford 10.