Highly regioselective friedländer reaction

Organic Letters

Volumn 3, Issue 8, 2001, Pages 1101-1103

  Hsiao, Yi ^a   Rivera, Nelo R ^a   Yasuda, Nobuyoshi ^a   Hughes, David L ^a   Reider, Paul J ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; KETONE; METHANOL; NAPHTHYRIDINE DERIVATIVE; PHOSPHATE;

ARTICLE; CHEMICAL MODEL; CHEMISTRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS;

CARBON; KETONES; MAGNETIC RESONANCE SPECTROSCOPY; METHANOL; MODELS, CHEMICAL; NAPHTHYRIDINES; PHOSPHATES;

EID: 0035912306     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006785v     Document Type: Article

References (13)

1. For a review, see: Hamada, Y.; Takeuchi, I. Yakugaku Zasshi 2000, 120, 206.
2. Hamada, Y.; Takeuchi, I. Chem. Pharm. Bull. 1971, 19, 1857.
3. For the newest review, see: Cheng, C.-C.; Yan, S.-J. In The Friedländer Synthesis of Quinolines; Dauben, W. C., Ed.; Organic Reactions; J. Wiley & Sons: New York, 1982; Vol. 28, p 37.
4. (a) Breitmaier, E.; Bayer, E. Tetrahedron 1970, 26, 5907.
5. (b) Veronese. A. C.; Callegari, R.; Salah, S. A. A. Tetrahedron Let. 1990, 31, 3485.
6. (c) Veronese, A. C.; Callegari, R.; Morelli, C. F. Tetrahedron 1995, 51, 12277.
7. Corey, E. J.; Kwiatkowski, G. T. J. Am. Chem. Soc. 1966, 88, 5654.
8. Commercially available from Aldrich.
9. The synthesis of 2b followed a standard procedure: (a) Kanemasa, S.; Otsuka, T.; Doi, K.; Tsuge, O.; Wada, E. Synthesis 1990, 1167.
10. CP = 128.3 Hz).
11. Delamarche, I.; Mosset, P. J. Org. Chem. 1994, 59, 5453.
12. Rivera, N. R.; Hsiao, Y.; McWilliams, C.; Cowen, J. A.; Armstrong, J.; Yasuda, N.; Hughes, D. L. Synth. Commun. In press.
13. max ≤ 41°C. The solution was stirred for 30 min, after which the remainder of the aldehyde (0.2 equiv) was added over 3 min. The reaction was allowed to stir overnight at room temperature (20°C). The crude mixture was concentrated, and the residue was dissolved in EtOAc. After a water wash, the organic solution was concentrated to give the desired naphthyridine product.