A simple one-pot preparation of 2-pyridones from acyl isocyanates utilizing trimethylsilylketene

Tetrahedron Letters

Volumn 37, Issue 28, 1996, Pages 4973-4976

  Takaoka, Kiyo ^a   Aoyama, Toyohiko ^a   Shioiri, Takayuki ^a  

^a NAGOYA CITY UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

2 PYRIDONE DERIVATIVE; DICARBOXYLIC ACID DERIVATIVE; ISOCYANIC ACID DERIVATIVE; KETENE DERIVATIVE;

ARTICLE; COLUMN CHROMATOGRAPHY; SYNTHESIS;

EID: 0030575399     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00982-3     Document Type: Article

References (9)

1. 1. Ito, T.; Aoyama, T.; Shioiri, T. Tetrahedron Lett. 1993, 34, 6583-6586.
2. 2. Takaoka, K.; Aoyama, T.; Shioiri, T. Synlett 1994, 1005-1006.
3. 3. Speziale, A. J.; Smith, L. R. J. Org. Chem. 1963, 28, 1805-1811.
4. 4. a) Zakhs, V. É.; Yakovlev, I. P.; Smorygo, N. A.; Gindin, V. A.; Ivin, B. A. Chem. Heterocycl. Compd. USSR 1986, 325-332;
5. b) Zakhs, V. É.; Yakovlev, I. P.; Tret'yakov, A. A.; Gindin, V. A.; Prep'yalov, A. V.; Ivin, B. A. J. Org. Chem. USSR 1991, 27, 744-751.
6. 3) δ: 0.32 (s, 9H), 2.90-3.10 (m, 4H), 5.28 (s, 1H), and 7.18-7.31 (m, 5H).
7. 6. Boger, D. L.; Weinreb, S. M., "Hetero Diels-Alder Methodology in Organic Synthesis", ed. by Wasserman, H. H. Academic Press, Inc., 1987, Chapter 9; Steglich, W.; Jeschke, R.; Buschmann, E. Gazz. Chim. Ital. 1986, 116, 361-372.
8. 6. Boger, D. L.; Weinreb, S. M., "Hetero Diels-Alder Methodology in Organic Synthesis", ed. by Wasserman, H. H. Academic Press, Inc., 1987, Chapter 9; Steglich, W.; Jeschke, R.; Buschmann, E. Gazz. Chim. Ital. 1986, 116, 361-372.
9. 7. The atomic charges of 1a and methyl propiolate were calculated by AM1, see Dewar, M. J. S.; Zoebisch, E. G.; Healy, E. F.; Stewart, J. J. P. J. Am. Chem. Soc. 1985, 107, 3902-3909.