The conversion of mixed N,O-diacylated 2-aminophenols to 2-substituted benzoxazoles

Heterocycles

Volumn 51, Issue 5, 1999, Pages 979-982

  DeLuca, Mark R ^a   Taraporewala, Irach B ^a   Kerwin, Sean M ^a  

^a UNIVERSITY OF TEXAS AT AUSTIN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 AMINOPHENOL; BENZOXAZOLE DERIVATIVE;

ACYLATION; ANALYTIC METHOD; ARTICLE; CATALYSIS; CYCLIZATION; DRUG SYNTHESIS; ELECTRON TRANSPORT; HYDROLYSIS; REACTION ANALYSIS;

EID: 0033133981     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-99-8509     Document Type: Article

References (19)

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2. D. V. Ramana and E. Kantharaj,J. Chem. Soc., Perkin Trans. 2, 1995, 1497. J. Kondo, N. Suzuki, T. Imaoka, T. Kawasaki, A. Nakanishi, and Y. Kawahara,Anal. Sci., 1994, 10, 17. P. E. Cassidy, 'Thermally Stable Polymers,' Dekker, New York, 1980.
3. D. V. Ramana and E. Kantharaj,J. Chem. Soc., Perkin Trans. 2, 1995, 1497. J. Kondo, N. Suzuki, T. Imaoka, T. Kawasaki, A. Nakanishi, and Y. Kawahara,Anal. Sci., 1994, 10, 17. P. E. Cassidy, 'Thermally Stable Polymers,' Dekker, New York, 1980.
4. M. R. DeLuca and S. M. Kerwin, Tetrahedron, 1997, 53, 457.
5. See for example: D. L. Boger and H. Zarrinmayeh, J. Org. Chem., 1990, 55, 1379.
6. T. Sakurai, K. Kubo, and H. Inoue, Rev. Met. Chem., 1997, 16, 213, and references therein.
7. The known compounds (1a) and (1c) were synthesized from the appropriate 2-amidophenol according to the literature procedure: A. L. LeRosen and E. D. Smith, J. Am. Chem. Soc., 1948, 70, 2705. Compound (1b) was synthesized according to literature procedure. All compounds provided satisfactory spectral and elemental analysis data. All benzoxazoles (2a-d) are known compounds and their structures confirmed by comparison with literature values: H. Gershon, D. D. Clarke, and M. Gershon, Montash. Chem., 1993, 124, 367.
8. The known compounds (1a) and (1c) were synthesized from the appropriate 2-amidophenol according to the literature procedure: A. L. LeRosen and E. D. Smith, J. Am. Chem. Soc., 1948, 70, 2705. Compound (1b) was synthesized according to literature procedure. All compounds provided satisfactory spectral and elemental analysis data. All benzoxazoles (2a-d) are known compounds and their structures confirmed by comparison with literature values: H. Gershon, D. D. Clarke, and M. Gershon, Montash. Chem., 1993, 124, 367.
9. 4: C, 67.36; H, 5.30; N, 4.91. Found: C, 67.32; H, 5.43; N, 4.85.
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11. H. Lindemann, H. Koenitzer, and S. Romanoff, Ann. Chem., 1927, 456, 303. Compounds (6a) and (8a) had melting points and structural data consistent with the literature values.
12. 5OMe) to benzoxazole occurs rapidly under these reaction conditions.
13. T. H. Fife, T. J. Przystas, and M. P. Pujari, J. Am. Chem. Soc., 1988, 110, 8157, and references cited therein.
14. Even in cases in which either nitrogen or oxygen atoms of the amide could reasonably participate in carbonyl attack, attack by the nitrogen atom is observed: S. W. King, R. Natarajan, R. Bembi, and T. H. Fife, J. Am. Chem. Soc., 1992, 114, 10715.
15. The small amount of benzoxazole product in which the 2-substituent is derived from the O-acyl group of the starting N,O-diacyl-2-aminophenol may arise from this type of process. Alternatively, this may arise from the well-established N- to O- rearrangement of mixed N,O-diacylated 2-aminophenols: E. D. Smith and L. Elrod, Jr., J. Org. Chem., 1977, 42, 652.
16. L. A. Reiter and B. P. Jones, J. Org. Chem., 1997, 62, 2808. J. Rahil and R. F. Pratt, J. Chem. Soc., Perkin Trans. 2, 1991, 947.
17. L. A. Reiter and B. P. Jones, J. Org. Chem., 1997, 62, 2808. J. Rahil and R. F. Pratt, J. Chem. Soc., Perkin Trans. 2, 1991, 947.
18. R. Mazurkiewicz, Monatsh. Chem., 1988, 119, 1279.
19. We gratefully acknowledge research support from the US Public Health Service Grant GM-50892.