A novel hydride-mediated reductive rearrangement of amide: a facile synthesis of pyrimidyl and triazinyl amines

Tetrahedron Letters

Volumn 49, Issue 3, 2008, Pages 495-499

  Chen, Xiang ^a   Wu, Jun ^a   Shang, Zhicai ^a   Chen, Meifeng ^a   Sun, Yanping ^a   Lv, Jing ^a   Lei, Meikang ^a   Zhang, Peizhi ^b  

^a ZHEJIANG UNIVERSITY   (China)

^b ZHEJIANG UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; AMINE; BENZAMIDE DERIVATIVE; LITHIUM DERIVATIVE; PYRIMIDINE DERIVATIVE; SODIUM DERIVATIVE; TRIAZINE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; REACTION ANALYSIS; REDUCTION; SYNTHESIS;

EID: 37249050510     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.11.096     Document Type: Article

References (32)

1. Micovic V.M., and Mihailovic M.L. J. Org. Chem. 18 (1953) 1190-1200
2. Brown H.C., and Tsukamoto A. J. Am. Chem. Soc. 83 (1961) 4549-4552
3. Seyden-Penne J. Reductions by the Alumino- and Borohydrides in Organic Synthesis. 2nd ed. (1997), Wiley, New York p 99-110
4. Brosius A.D., Overman L., and Schwink L. J. Am. Chem. Soc. 121 (1999) 700-709
5. Smith M.B. Organic Synthesis. 2nd ed. (2002), McGraw-Hill, New York p 314
6. Ghosh A.K., Shin D., Downs B., Koelsch G., Lin X., Ermolieff J., and Tang J. J. Am. Chem. Soc. 122 (2000) 3522-3523
7. Van Brabandt W., Dejaegher Y., Van Landeghem R., and De Kimpe N. Org. Lett. 8 (2006) 1101-1104
8. Soon Cha J., and Brown H.C. J. Org. Chem. 58 (1993) 4727-4731
9. Pettit G.R., Eastham S.A., Melody N., Orr B., Herald D.L., McGregor J., Knight J.C., Doubek D.L., and Pettit G.R. J. Nat. Prod. 69 (2006) 7-13
10. Atta U.R., Anjum S., Farooq A., Khan M.R., Parveen Z., and Choudhary M.I. J. Nat. Prod. 61 (1998) 202-206
11. Nakao Y., Yoshida W.Y., Takada Y., Kimura J., Yang L., Mooberry S.L., and Scheuer P.J. J. Nat. Prod. 67 (2004) 1332-1340
12. Tan R.X., Jensen P.R., Williams P.G., and Fenical W. J. Nat. Prod. 67 (2004) 1374-1382
13. Ruiz-Caro J., Basavapathruni A., Kim J.T., Bailey C.M., Wang L., Anderson K.S., Hamilton A.D., and Jorgensen W.L. Bioorg. Med. Chem. Lett. 16 (2006) 668-671
14. Thakur V.V., Kim J.T., Hamilton A.D., Bailey C.M., Domaoal R.A., Wang L., Anderson K.S., and Jorgensen W.L. Bioorg. Med. Chem. Lett. 16 (2006) 5664-5667
15. Nagata T., Masuda K., Maeno S., and Miura I. Pest Manage. Sci. 60 (2004) 399-407
16. Brown D.J. In: Katritzky A.R., and Rees C.W. (Eds). Comprehensive Heterocyclic Chemistry Vol. 3, Chapter 2.13 (1984), Pergamon, Oxford
17. Pratap P., Roy A.D., Kushwaha S.P., Geol A., Roy R., and Ram V.J. Tetrahedron Lett. 48 (2007) 5845-5849
18. Herrera A., Alvarez R.M., Chioua R., and Almy J. Tetrahedron Lett. 47 (2006) 5463-5465
19. For the first step, see:. Wu J., Cheng J., and Lu L. J. Agric. Food Chem. 54 (2006) 5954-5957
20. Bessard Y., and Crettaz R. Tetrahedron 56 (2000) 4739-4745
21. For the second step, see:. Horenstein B.A., and Nakanishi K. J. Am. Chem. Soc. 111 (1989) 6242-6246
22. Woydowski K., and Liebscher J. Tetrahedron 55 (1999) 9205-9220
23. 4: To a suspension solution of lithium aluminum hydride (9 mmol, 343 mg) or sodium borohydride (18 mmol, 702 mg) in tetrahydrofuran (20 mL) was added dropwise 1 (1.5 mmol) in tetrahydrofuran (15 mL) at room temperature for about 20 min. The mixture was refluxed for 2-4 h. Afterwards, the reaction was then cooled and quenched by the careful addition of ice water (15 mL) and sodium hydroxide (10%, 15 mL) for 1 h. The solid was filtered off under reduced pressure and washed with ethyl acetate (3 × 20 mL). The organic layer was washed with brine (3 × 20 mL) and dried over anhydrous magnesium sulfate. The solvent was removed under vacuo and the residue was purified by column chromatography on silica gel with petroleum ether-ethyl acetate (10:1) to afford the corresponding products 2 in 52-95% yield.
24. Kanth J.V.B., and Periasamy M. J. Org. Chem. 56 (1991) 5964-5965
25. McKennon M.J., and Meyers A.I. J. Org. Chem. 58 (1993) 3568-3571
26. The most popular synthetic method of such substituted pyrimidine amines is nucleophilic substitution of heterocyclic halides with neutral nitrogen nucleophiles with bases as catalysts. (a) Eur. Patent, 224339, 1987.
27. PCT Int. Patent, 2006068213, 2006.
28. Peng Z.-H., Journet M., and Humphrey G. Org. Lett. 8 (2006) 395-398
29. Bursavich M.G., Lombardi S., and Gilbert A.M. Org. Lett. 7 (2005) 4113-4116
30. Cherng Y.J. Tetrahedron 58 (2002) 887-890
31. 3 in refluxing THF or DMSO. However, trace of amine 2a was obtained in THF under reflux for 10 h, and in refluxing DMSO the reaction afforded 2a only in 20% yield.
32. Jarkas N., McConathy J., Voll R.J., and Goodman M.M. J. Med. Chem. 48 (2005) 4254-4265