Interesting acid-catalyzed O-N-type smiles rearrangement reactions of 2-pyrimidinyloxy-N-arylbenzylamine derivatives

Synlett

Volumn , Issue 8, 2005, Pages 1239-1242

  Wang, Hao Yang ^a   Liao, Yuan Xi ^a   Guo, Yin Long ^a   Tang, Qing Hong ^a   Lu, Long ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

2 Pyrimidinyloxy N arylbenzylamine; Acidic conditions; Smiles rearrangement

Indexed keywords

2 PYRIMIDINYLOXY N BENZYLAMINE DERIVATIVE; ACETIC ACID; ACETONE; ACID; BENZYLAMINE DERIVATIVE; PHENOL DERIVATIVE; PYRIMIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; REPRODUCIBILITY; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS; TECHNIQUE; TEMPERATURE DEPENDENCE;

EID: 19944398117     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-865235     Document Type: Article

References (18)

1. (a) Warren, L. A.; Smiles, S. J. Chem. Soc. 1930, 956.
2. (b) Warren, L. A.; Smiles, S. J. Chem. Soc. 1930, 1327.
3. (c) Warren, L. A.; Smiles, S. J. Chem. Soc. 1931, 2207.
4. Review: Truce, W. E.; Kreider, E. M.; Brand, W. W. Org. React., 18; Wiley: New York, 1970, 99.
5. Review: Rádl, S. Advances in Heterocyclic Chemistry, 83; Academic Press: San Diego, 2002, 189.
6. For Smiles rearrangement, see: (a) Weidner, J. J.; Weintraub, P. M. J. Heterocycl. Chem. 1997, 34, 1857.
7. (b) Huber, V. J.; Bartsch, R. A. Tetrahedron 1998, 54, 9281.
8. (c) Anelli, P. L.; Brocchetta, M.; Calabi, L.; Secchi, C.; Uggeri, F.; Verona, S. Tetrahedron 1997, 53, 11919.
9. (d) Weidner, J. J.; Weintraub, P. M.; Schnettler, R. A.; Peet, N. P. Tetrahedron 1997, 53, 6303.
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11. (a) Lu, L.; Chen, J.; Cai, X.; Li, M. Z.; Wu, Y.; Wang, Y. H. Patent CN 1323788-A, 2001; Chem. Abstr. 2002, 137 74803.
12. (b) Lu, L.; Chen, J.; Wu, J.; Ling, W.; Mao, L. S.; Li, M. Z.; Cai, X.; Peng, W. L.; Wu, Y.; Wu, S. G.; Wang, H. J.; Wang, G. C.; Cui, H.; Han, S. D.; Qiu, W. L.; Wang, Y. H. World Patent WO 200234724-A1, 2002; Chem. Abstr. 2002, 136, 355244.
13. Analytical data for these compounds are available upon request from the authors. Compounds 1a and 1c have been used in rape fields in China.
14. Wang, H.-Y.; Guo, Y.-L.; Lu, L. J. Am. Soc. Mass Spectrom. 2004, 75, 1820.
15. For O-N-type Smiles rearrangement, see: (a) Kleb, K. G. Angew. Chem., Int. Ed. Engl. 1968, 7, 291.
16. (b) Selvakumar, N.; Srinivas, D.; Azhagan, A. M. Synthesis 2002, 2421.
17. For acid-catalyzed Smiles rearrangement, see: (a) Rodig, O. R.; Collier, R. E.; Schlatzer, R. K. J. Org. Chem. 1964, 29, 2652.
18. (b) Shin, J. M.; Cho, Y. M.; Sachs, G. J. Am. Chem. Soc. 2004, 126, 7800.