"Pictet-Spengler-like" synthesis of tetrahydro-β-carbolines under hydrolytic conditions. Direct use of azalactones as phenylacetaldehyde equivalents

Journal of Organic Chemistry

Volumn 61, Issue 22, 1996, Pages 7937-7939

  Audia, James E ^a   Droste, James J ^a   Nissen, Jeffrey S ^a   Murdoch, Gwyn L ^a   Evrard, Deborah A ^a  

^a ELI LILLY AND COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BETA CARBOLINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; TECHNIQUE;

EID: 0029798910     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9600868     Document Type: Article

References (16)

1. Pictet, A., Spengler, T. Ber. 1922, 44, 2030. Whaley, W.; Govindochari, T. Organic Reactions; John Wiley & Sons, Inc.: New York, 1951; Vol. VI, p 74. Whaley, W.; Govindochari, T. Organic Reactions; John Wiley & Sons, Inc.: New York, 1951; Vol. VI, p 151. Sundberg, R. The Chemistry of Indoles; Academic Press: New York, 1970; p 236. Abramovitch, R.; Spencer, I. Advances in Heterocyclic Chemistry; Academic Press: New York, 1964; Vol. 3, p 79. Ungemach, F.; Cook, J. M. Heterocycles 1978, 9, 1089.
2. Pictet, A., Spengler, T. Ber. 1922, 44, 2030. Whaley, W.; Govindochari, T. Organic Reactions; John Wiley & Sons, Inc.: New York, 1951; Vol. VI, p 74. Whaley, W.; Govindochari, T. Organic Reactions; John Wiley & Sons, Inc.: New York, 1951; Vol. VI, p 151. Sundberg, R. The Chemistry of Indoles; Academic Press: New York, 1970; p 236. Abramovitch, R.; Spencer, I. Advances in Heterocyclic Chemistry; Academic Press: New York, 1964; Vol. 3, p 79. Ungemach, F.; Cook, J. M. Heterocycles 1978, 9, 1089.
3. Pictet, A., Spengler, T. Ber. 1922, 44, 2030. Whaley, W.; Govindochari, T. Organic Reactions; John Wiley & Sons, Inc.: New York, 1951; Vol. VI, p 74. Whaley, W.; Govindochari, T. Organic Reactions; John Wiley & Sons, Inc.: New York, 1951; Vol. VI, p 151. Sundberg, R. The Chemistry of Indoles; Academic Press: New York, 1970; p 236. Abramovitch, R.; Spencer, I. Advances in Heterocyclic Chemistry; Academic Press: New York, 1964; Vol. 3, p 79. Ungemach, F.; Cook, J. M. Heterocycles 1978, 9, 1089.
4. Pictet, A., Spengler, T. Ber. 1922, 44, 2030. Whaley, W.; Govindochari, T. Organic Reactions; John Wiley & Sons, Inc.: New York, 1951; Vol. VI, p 74. Whaley, W.; Govindochari, T. Organic Reactions; John Wiley & Sons, Inc.: New York, 1951; Vol. VI, p 151. Sundberg, R. The Chemistry of Indoles; Academic Press: New York, 1970; p 236. Abramovitch, R.; Spencer, I. Advances in Heterocyclic Chemistry; Academic Press: New York, 1964; Vol. 3, p 79. Ungemach, F.; Cook, J. M. Heterocycles 1978, 9, 1089.
5. Pictet, A., Spengler, T. Ber. 1922, 44, 2030. Whaley, W.; Govindochari, T. Organic Reactions; John Wiley & Sons, Inc.: New York, 1951; Vol. VI, p 74. Whaley, W.; Govindochari, T. Organic Reactions; John Wiley & Sons, Inc.: New York, 1951; Vol. VI, p 151. Sundberg, R. The Chemistry of Indoles; Academic Press: New York, 1970; p 236. Abramovitch, R.; Spencer, I. Advances in Heterocyclic Chemistry; Academic Press: New York, 1964; Vol. 3, p 79. Ungemach, F.; Cook, J. M. Heterocycles 1978, 9, 1089.
6. Pictet, A., Spengler, T. Ber. 1922, 44, 2030. Whaley, W.; Govindochari, T. Organic Reactions; John Wiley & Sons, Inc.: New York, 1951; Vol. VI, p 74. Whaley, W.; Govindochari, T. Organic Reactions; John Wiley & Sons, Inc.: New York, 1951; Vol. VI, p 151. Sundberg, R. The Chemistry of Indoles; Academic Press: New York, 1970; p 236. Abramovitch, R.; Spencer, I. Advances in Heterocyclic Chemistry; Academic Press: New York, 1964; Vol. 3, p 79. Ungemach, F.; Cook, J. M. Heterocycles 1978, 9, 1089.
7. Valls, N.; Segarra, V. M.; Bosch, J. Heterocycles 1986, 24, 943.
8. Knabe, J.; Suggau, R. Arch. Pharmaz. 1973, 306, 500. Hudlicky, T.; Kutchan, T. M.; Shen, G.; Sutliff, V. E.; Coscia, C. J. J. Org. Chem. 1981, 46, 1738.
9. Knabe, J.; Suggau, R. Arch. Pharmaz. 1973, 306, 500. Hudlicky, T.; Kutchan, T. M.; Shen, G.; Sutliff, V. E.; Coscia, C. J. J. Org. Chem. 1981, 46, 1738.
10. Vercauteren, J.; Lavaud, C.; Levy, J.; Massiot, G. J. Org. Chem. 1984, 49, 2278.
11. Audia, J. E.; Evrard, D. A.; Murdoch, G. R.; Droste, J. J.; Nissen, J. S.; Schenck, K. S.; Fludzinski, P.; Cohen, M. L. J. Med. Chem. 1996, 39, 2773.
12. ACD database searching indicated commercial availability of only the parent phenylacetaldehyde. Conversely, a similar ACD database search indicated commercial availability of > 500 benzaldehyde derivatives.
13. Plöchl, E. Ber. 1883, 16, 2815.
14. We note the exception of 2,6-disubstituted benzaldehydes in which azalactone formation fails, presumably due to steric factors.
15. Snyder, H. R.; Buck, J. S.; Ide, W. S. Organic Syntheses; Blatt, A. H., Ed.; John S. Wiley & Sons: New York, 1943; Collect. Vol. II, p 333.
16. Our observation was that single stage hydrolysis was an effective, albeit slow, means of preparation of the phenylpyruvic acids. See: MacDonald, S. F. J. Chem. Soc. 1948, 376.