A Mild Method for the Formation and in Situ Reaction of Imidoyl Chlorides: Conversion of Pyridine-1-oxides to 2-Aminopyridine Amides

Organic Letters

Volumn 4, Issue 18, 2002, Pages 3127-3129

  Manley, Peter J ^a   Bilodeau, Mark T ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 AMINOPYRIDINE; ALPHA-AMINOPYRIDINE; AMIDE; AMINOPYRIDINE DERIVATIVE; CHLORIDE; OXALIC ACID DERIVATIVE; OXALYL CHLORIDE; OXIDE;

ARTICLE; CHEMISTRY; METHODOLOGY; SYNTHESIS;

AMIDES; AMINOPYRIDINES; CHEMISTRY, PHARMACEUTICAL; CHLORIDES; OXALATES; OXIDES;

EID: 0037026456     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0264556     Document Type: Article

References (14)

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2. Abramovitch, R. A.; Singer, G. M. J. Am. Chem. Soc. 1969, 91, 5672. Abramovitch, R. A.; Singer, G. M. J. Org. Chem. 1974, 39, 1795. Abramovitch, R. A.; Rogers, R. B. J. Org. Chem. 1974, 39, 1802. Abramovitch, R. A.; Pilski, J.; Konitz, A.; Tomasik, P. J. Org. Chem. 1983, 48, 4391.
3. Abramovitch, R. A.; Singer, G. M. J. Am. Chem. Soc. 1969, 91, 5672. Abramovitch, R. A.; Singer, G. M. J. Org. Chem. 1974, 39, 1795. Abramovitch, R. A.; Rogers, R. B. J. Org. Chem. 1974, 39, 1802. Abramovitch, R. A.; Pilski, J.; Konitz, A.; Tomasik, P. J. Org. Chem. 1983, 48, 4391.
4. Abramovitch, R. A.; Singer, G. M. J. Am. Chem. Soc. 1969, 91, 5672. Abramovitch, R. A.; Singer, G. M. J. Org. Chem. 1974, 39, 1795. Abramovitch, R. A.; Rogers, R. B. J. Org. Chem. 1974, 39, 1802. Abramovitch, R. A.; Pilski, J.; Konitz, A.; Tomasik, P. J. Org. Chem. 1983, 48, 4391.
5. Kantlehner, W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991, Vol. 6, p 485.
6. A procedure employing 1.5 equiv of phosgene in the presence of pyridine has previously been described: Fujimoto, K.; Watanabe, T.; Abe, J.; Okawa, K. Chem. Ind. 1971, 175.
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10. Abramovitch, R. A.; Rogers, R. B. Tetrahedron Lett. 1971, 22, 1951. Abramovitch, R. A.; Rogers, R. B.; Singer, G. M. J. Org. Chem. 1975, 40, 41.
11. For the formation of imino triflates and addition of nucleophiles, see: Thomas, E. W. Synthesis 1993, 767. Charette, A. B.; Chua, P. J. Org. Chem. 1998, 63, 908. Charette, A. B.; Grenon, M. Tetrahedron Lett. 2000, 41, 1677. Charette, A. B.; Grenon, M.; Lemire, A.; Pourashraf, M.; Martel, J. J. Am. Chem. Soc. 2001, 123, 11829.
12. For the formation of imino triflates and addition of nucleophiles, see: Thomas, E. W. Synthesis 1993, 767. Charette, A. B.; Chua, P. J. Org. Chem. 1998, 63, 908. Charette, A. B.; Grenon, M. Tetrahedron Lett. 2000, 41, 1677. Charette, A. B.; Grenon, M.; Lemire, A.; Pourashraf, M.; Martel, J. J. Am. Chem. Soc. 2001, 123, 11829.
13. For the formation of imino triflates and addition of nucleophiles, see: Thomas, E. W. Synthesis 1993, 767. Charette, A. B.; Chua, P. J. Org. Chem. 1998, 63, 908. Charette, A. B.; Grenon, M. Tetrahedron Lett. 2000, 41, 1677. Charette, A. B.; Grenon, M.; Lemire, A.; Pourashraf, M.; Martel, J. J. Am. Chem. Soc. 2001, 123, 11829.
14. For the formation of imino triflates and addition of nucleophiles, see: Thomas, E. W. Synthesis 1993, 767. Charette, A. B.; Chua, P. J. Org. Chem. 1998, 63, 908. Charette, A. B.; Grenon, M. Tetrahedron Lett. 2000, 41, 1677. Charette, A. B.; Grenon, M.; Lemire, A.; Pourashraf, M.; Martel, J. J. Am. Chem. Soc. 2001, 123, 11829.