A convenient synthesis of N-methoxy-N-methylamides from carboxylic acids using S,S-Di(2-pyridyl) dithiocarbonate

Bulletin of the Korean Chemical Society

Volumn 22, Issue 4, 2001, Pages 421-423

  Lee, Jae In ^a   Park, Hyun ^a  

^a Duksung Women's University   (South Korea)

Author keywords

Bis(trichloromethyl)carbonate, N,O Dimethylhydroxylamine hydrochloride; N Methoxy N methylamide; S,S Di(2 pyridyl) dithiocarbonate

Indexed keywords

AMIDE; BIS(TRICHLOROMETHYL)CARBONATE; CARBONIC ACID DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; DI(2 PYRIDYL)DITHIOCARBONATE; N METHOXY N METHYLAMIDE DERIVATIVE; N,O DIMETHYLHYDROXYLAMINE; UNCLASSIFIED DRUG;

NOTE; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; SYNTHESIS;

EID: 0000865810     PISSN: 02532964     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Note

References (25)

1. (a) Nahm, S.; Weinreb, S. M. Tetrahedron Lett. 1981, 22, 3815.
2. (b) For a review on the application of N-methoxy-N-methylamides: Sibi, M. P. Org. Prep. Proced. Int. 1993, 25, 15.
3. Davies, D. T.; O'Hanlon, P. J. Synth. Comm. 1988, 18, 2273.
4. Einhorn, J.; Einhorn, C.; Luche, J. L. Synth. Comm. 1990, 20, 1105.
5. (a) Fehrentz, J. A.; Castro, B. Synthesis 1983, 676.
6. (b) Wernic, D.; DiMaio, J.; Adams, J. J. Org. Chem. 1989, 54, 4224.
7. Maugras, I.; Poncet, J.; Jouin, P. Tetrahedron 1990, 46, 2807.
8. (d) D'Aniello, F.; Mann, A. J. Org. Chem. 1996, 61, 4870.
9. Poss, M. A.; Reid, J. A. Tetrahedron Lett. 1992, 33, 1411.
10. (a) Braun, M.; Waldmuller, D. Synthesis 1989, 856.
11. (b) Brenner-Weiβ, G.; Giannis, A.; Sandhoff, K. Tetrahedron 1992, 48, 5855.
12. Sibi, M. P.; Stessman, C. C.; Schultz, J. A. Synth. Comm. 1995, 25, 1255.
13. Wen, J. J.; Crews, C. M. Tetrahedron: Asymmetry 1998, 9, 1855.
14. (a) Angelastro, M. R.; Peet, N. P.; Bey, P. J. Org. Chem. 1989, 54, 3913.
15. (b) Angelastro, M. R.; Mehdi, S.; Burkhart, J. P.; Peet, N. P.; Bey, P. J. Med. Chem. 1990, 33, 13.
16. (c) Angelastro, M. R.; Burkhart, J. P.; Bey, P.; Peet, N. P. Tetrahedron Lett. 1992, 33, 3265.
17. (d) Murray, A.; Proctor, G. R.; Murray, P. J. ibid. 1995, 36, 291.
18. Irako, N.; Hamada, Y.; Shioiri, T. Tetrahedron 1992, 48, 7251.
19. Raghuram, T.; Vijaysaradhi, S.; Singh, I.; Singh, J. Synth. Comm. 1999, 29, 3215.
20. (a) Williams, J. M.; Jobson, R. B.; Yasuda, N.; Marchesini, G.; Dolling, U. H.; Grabowski, E. J. J. Tetrahedron Lett. 1995, 36, 5461.
21. (b) Iseki, K.; Asada, D.; Kuroki, Y. J. Fluorine Chem. 1999, 97, 85.
22. (a) Garigipati, R. S.; Tschaen, D. M.; Weinreb, S. M. J. Am. Chem. Soc. 1985, 707, 7790.
23. (b) Shimizu, T.; Osako, K.; Nakata, T. Tetrahedron Lett. 1997, 38, 2685.
24. (a) Evans, D. A.; Kaldor, S. W.; Jones, T. K.; Clardy, J.; Stout, T. J. J. Am. Chem. Soc. 1990, 112, 7001.
25. (b) Davis, F. A.; Kasu, P. V. N. Tetrahedron Lett. 1998, 39, 6135.