An auto-catalyzed Mannich-type reaction for synthesis of highly substituted α-aminomethylphosphonates

Synthesis

Volumn , Issue 6, 2003, Pages 887-893

  Yang, Rifang ^a   Zhao, Rusheng ^a   Zhao, Lizhi ^a   Yun, Liuhong ^a   Wang, Hai ^a  

^a BEIJING INSTITUTE OF PHARMACOLOGY AND TOXICOLOGY   (China)

Author keywords

Autocatalysis; Hydroxybenzaldehyde; Mannich type reaction; Secondary amine; amino phosphonates

Indexed keywords

ALCOHOLS; ALDEHYDES; AMINES; CATALYSIS; HEATING; PHENOLS;

AUTO-CATALYZED REACTIONS;

SYNTHESIS (CHEMICAL);

ALCOHOL; ALDEHYDE DERIVATIVE; METHYLPHOSPHONIC ACID; PHOSPHITE;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; MANNICH REACTION; MOLECULAR DYNAMICS; TEMPERATURE;

EID: 0038706127     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-38679     Document Type: Article

References (17)

1. Fields, E. K. J. Am. Chem. Soc. 1952, 74, 1528.
2. Moedritzer, K.; Irani, R. R. J. Org. Chem. 1966, 31, 1603.
3. Dai, Q.; Chen, R.-Y. Chem. J. Chin. Univ. 1997, 18, 64.
4. Tyka, R.; Hagele, G. Synthesis 1984, 218.
5. Qian, C.; Huang, T. J. Org. Chem. 1998, 63, 4125.
6. Heydari, A.; Karimian, A.; Ipaktschi, J. Tetrahedron Lett. 1998, 39, 6729.
7. (a) Wang, Q.; Mu, S.-H.; Yang, R.-F.; Wang, H. Chin. Pharmacol. Bull. 2002, 18, 468.
8. (b) Shan, L.-M. PhD. Dissertation; Beijing Institute of Pharmacology and Toxicoloy: China, 2002.
9. (c) Yang, R.; Wang, H. Chinese Patent Application CN01137268.0, 2001.
10. (d) Wang, H.; Yang, R. Chinese Patent Application CN01137273.7, 2001.
11. (e) Wang, H.; Yang, R. Chinese Patent Application CN01137274.5, 2001.
12. Schreiber, S. L. Science 2000, 287, 1964.
13. Experiments were performed in which 2′-hydroxyacetophenone and benzaldehydes without a phenolic hydroxy group were used in place of the corresponding benzaldehydes with a phenolic hydroxy group, and were respectively treated with diethyl phosphite and the corresponding secondary amines or their hydrochloride salts in the presence or absence of 1 equivalent of acetic acid in the same way and under the same conditions as stated in the general procedure.
14. Anilines such as p-bromoaniline, p-hydroxyaniline and 2,3-dimethyl-2-butylamine were reacted with piperonal and diethyl phosphite producing the corresponding phosphonates in excellent yields.
15. Takahashi, H.; Yoshika, M.; Imai, N.; Onimura, K.; Kobayashi, S. Synthesis 1994, 763.
16. Burckhalter, J. H.; Leib, R. I. J. Org. Chem. 1961, 26, 4078.
17. Monti, S. A.; Johnson, W. O. Tetrahedron 1970, 26, 3685.