Convenient method of synthesizing 3-ethoxycarbonyl indoles

Journal of Organic Chemistry

Volumn 71, Issue 12, 2006, Pages 4675-4677

  Islam, M Shahidul ^a   Brennan, Courtney ^a   Wang, Qinwei ^a   Hossain, M Mahmun ^a  

^a UNIVERSITY OF WISCONSIN MILWAUKEE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

3-ETHOXYCARBONYL INDOLES; CATALYTIC REDUCTION; HYDROXYPROPENOIC ACID ESTERS;

CATALYSIS; ESTERS; REDUCTION; SYNTHESIS (CHEMICAL);

ALCOHOLS;

3 ETHOXYCARBONYLINDOLE; 3 HYDROXYPROPENOIC ACID ESTER; ACRYLIC ACID DERIVATIVE; AMMONIUM ACETATE; AMMONIUM FORMATE; BENZALDEHYDE; CARBONYL DERIVATIVE; CHLORIDE; DIAZOACETIC ACID ETHYL ESTER; FLUINDOSTATIN; INDOLE DERIVATIVE; INDOMETACIN; INFUSORIAL EARTH; LEAD; LEWIS ACID; PYRUVIC ACID; REDUCING AGENT; TITANIUM; TRYPTOPHAN; UNCLASSIFIED DRUG; VINBLASTINE; VINCRISTINE SULFATE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; DRUG STRUCTURE; DRUG SYNTHESIS; HYDROGENATION; POLYMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION TIME; REDUCTION;

CATALYSIS; HYDROGENATION; INDOLES; METHODS;

EID: 33744911957     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0601821     Document Type: Article

References (38)

1. (a) Rahman, A.; Basha, A. Indole Alkaloids; Harwood Academic Publishers: Amsterdam, The Netherlands, 1998; p 141.
2. (b) Gupta, R. R. Heterocyclic Chemistry; Springer Publishing: New York, 1999; Vol. 2, p 193.
3. Physicians Desk Reference, 51st ed.; Medical Economics, Co.: Oradell, New Jersey, 1997; p 2395.
4. Physicians Desk Reference, 51st ed.; Medical Economics, Co.: Oradell, New Jersey, 1997; p 1723.
5. (a) Physicians Desk Reference, 51st ed.; Medical Economics, Co.: Oradell, New Jersey, 1997; p 1521.
6. (b) Gupta, R. R. Heterocyclic Chemistry; Springer Publishing: New York, 1999; Vol. 2, p 192.
7. For a review on medicinal chemistry of Vinblastine, see: In The Alkaloids: Antitumor Bisindole Alkaloids from Catharanthus roseus (L.); Brossi, A., Suffness, M., Eds.; Academic Press, Inc.: San Diego, CA, 1990; Vol. 37, pp 133-204.
8. Meister, A. The Biochemistry of The Amino Acids, 2nd ed.; Academic Press: New York, 1965; p 202.
9. (a) Sundberg, R. J. The Chemistry of Indoles; Academic Press: New York, 1970; p 142.
10. (b) Jones, A. R. In Comprehensive Heterocyclic Chemistry; Katrizky, A. R., Rees, C. W., Eds.; Pergamon Press: Oxford, 1984; Vol. 4, p 334.
11. (c) Gupta, R. R. Heterocyclic Chemistry; Springer Publishing: New York, 1999; Vol. 2, p 199.
12. (d) Nakazaki, M.; Yamamoto, K. J. Org. Chem. 1976, 41, 1877.
13. For reviews, see: (a) Gribble, G. W. J. Chem. Soc., Perkin Trans. 1 2000, 1045.
14. (b) Gilchrist, T. L. J. Chem. Soc., Perkin Trans. 1 1999, 2848.
15. (c) Sundberg, R. J. Indoles; Academic Press: San Diego, CA, 1996.
16. (d) Moody, C. J. Synlett 1994, 681.
17. (e) Gribble, G. W. Contemp. Org. Synth. 1994, 145.
18. (f) Pindur, U.; Adam, R. J. Heterocycl. Chem. 1988, 25, 1.
19. Aromatic aldehydes and ethyl diazoacetate are commercially available. Ethyl diazoacetate is also prepared in our laboratory following the known procedure: Searle, N. E. In Organic synthesis; Rabjohn, N., Ed.; Wiley: New York, 1963; Collect. Vol. No. IV, p 424. There is no difference in the yield of the products by using commercial ethyl diazoacetate or by using a freshly prepared one.
20. Mahmood, S. J.; Hossain, M. M. J. Org. Chem. 1998, 63, 3333.
21. Dudley, M.; Morshed, M. M.; Brennan, C.; Islam, M. S.; Ahmad, M. S.; Atuu, M. R.; Branstetter, B.; Hossain, M. M. J. Org. Chem. 2004, 69, 7599.
22. Faul, M. M. Tin (II) Chloride. In Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A., Ed.; Wiley: New York, 1995; Vol. 7, p 4893.
23. Ho, T.; Wong, C. M. Synthesis 1974, 45.
24. (a) Ram, S.; Ehrenkaufer, R. E. Tetrahedron Lett. 1984, 25, 3415.
25. (b) Kabalka, G. W.; Pace, R. D.; Wadgaokar, P. P. Synth. Commun. 1990, 20, 2453.
26. (a) Sundberg, R. J. The Chemistry of Indoles; Academic Press: New York, 1970; p 176.
27. (b) Jones, A. R. In Comprehensive Heterocyclic Chemistry; Katrizky, A. R., Rees, C. W., Eds.: Pergamon Press: Oxford, 1984; Vol. 4, p 317.
28. (c) Gupta, R. R. Heterocyclic Chemistry; Springer Publishing: New York, 1999; Vol. 2, p 194.
29. (a) Loewe, M.; Witzel, S.; Tappmeyer, S.; Albuschat, R. J. Heterocycl. Chem. 2004, 41, 3.
30. (b) Belley, M.; Scheigetz, J.; Dube, P.; Dolman, S. Synlett 2001, 2, 222.
31. (c) Prashad, M.; Vecchia, L. L.; Prasad, K.; Repic, O. Synth. Commun. 1995, 25, 95.
32. (d) van den Berg, E. M. M.; Baldew, A. U.; de Goede, A. T. J. W.; Rapp, J.; Lugtenburg, J. Recl. Trav. Chim. Pays-Bas 1988, 107, 73.
33. (e) Noland, W. E.; Selistedt, J. H. J. Org. Chem. 1966, 31, 345.
34. (a) Garcia, E. E.; Riley, J. G.; Fryer, R. I. J. Org. Chem. 1968, 33, 2868.
35. (b) Hossain, M. M. Synthesis of 2-Aryl Propenoic Acid Esters for the Production of Nonsteroidal Anti-inflammatory Drugs, US Patent 6,683205 B2, January 27, 2004.
36. (a) Cox, M.; Heidarizadeh, F.; Prager, R. H. Aust. J. Chem. 2000, 53, 665.
37. (b) Ang, K. H.; Prager, R. H.; Williams, C. G. Aust. J. Chem. 1995, 48, 567.
38. (c) Wender, P. A.; Cooper, C. B. Tetrahedron 1986, 42, 2985.