Dual nucleophilic catalysis with DABCO for the N-methylation of indoles

Journal of Organic Chemistry

Volumn 68, Issue 5, 2003, Pages 1954-1957

  Shieh, Wen Chung ^a   Dell, Steven ^a   Bach, Andrew ^a   Repič, Oljan ^a   Blacklock, Thomas J ^a  

^a NOVARTIS INSTITUTES FOR BIOMEDICAL RESEARCH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

NUCLEOPHILIC CATALYSIS;

ACYLATION; ALKYLATION; CATALYSTS;

CATALYSIS;

1,4 DIAZABICYCLO[2.2.2]OCTANE; CARBONIC ACID DERIVATIVE; INDOLE DERIVATIVE;

ACYLATION; ALKYLATION; ARTICLE; CATALYSIS; CATALYST; METHYLATION; QUANTUM YIELD; REACTION ANALYSIS;

EID: 0037424292     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0266644     Document Type: Article

References (27)

1. Zubay, G. Regulation of Gene Expression in Eukaryotes. In Biochemistry, 3rd ed.; Wm. C. Brown Publishers: Dubuque, Iowa, 1993; Chapter 30.
2. Stryer, L. Excitable Membranes and Sensory Systems. In Biochemistry, 2nd ed.; W. H. Freeman and Company: New York, 1981; Chapter 37.
3. Liu, X.; Wang, T.; Xu, Q.; Ma, C.; Cook, J. M. Tetrahedron Lett. 2000, 41, 6299.
4. Christophe, S.; Kuehm-Caubère, C.; Renard, P.; Pfeiffer, B.; Caubère, P. Tetrahedron Lett. 1998, 39, 9431.
5. For leading references using MeI, see: Hilton, S. T.; Ho, T. C. T.; Pljevaljcic, G.; Schulte, M.; Jones, K. J. Chem. Soc., Chem. Commun. 2001, 209.
6. Hilton, S. T.; Ho, T. C. T.; Pljevaljcic, G.; Jones, K. Org. Lett. 2000, 2, 2639.
7. Tratrat, C.; Giorgi-Renault, S.; Husson, H.-P. J. Org. Chem. 2000, 65, 6773.
8. de Koning, C. B.; Michael, J. P.; Rousseau, A. L. J. Chem. Soc., Perkin Trans. 1 2000, 1705.
9. 4, see: Ottoni, O.; Cruz, R.; Alves, R. Tetrahedron 1998, 54, 13915.
10. Jiang, X.; Tiwari, A,; Thompson, M.; Chen, Z.; Cleary, T. P.; Lee, T. B. Org. Proc. Res. Dev. 2001, 5, 604.
11. Bergman, J.; Norrby, P.-O.; Sand, P. Tetrahedron 1990, 46, 6113.
12. Shieh, W,-C.; Dell, S.; Repič, O. Org. Lett. 2001, 3, 4279.
13. Frenna, V.; Vivona, N.; Consiglio, G.; Spinelli, D. J. Chem. Soc., Perkin Trans. 2 1985, 1865.
14. Yu, C.; Liu, B.; Hu, L. J. Org. Chem. 2001, 66, 5413.
15. Kaye, P. T.; Robinson, R. S. Synth. Commun. 1996, 26, 2085.
16. Drewes, S. E.; Emslie, N. D.; Karodia, N. Synth. Commun. 1990, 20, 1915.
17. Linn, J. A.; McLean, E. W.; Kelly, J. L. J. Chem. Soc., Chem. Commun. 1994, 913.
18. All N-methylated indoles are known. For the methylated indole 1, see: Soll, R. M.; Park, J. A.; Rimele, T. J.; Heaslip, R. J.; Wojdan, A.; Oshiro, G.; Grimes, D.; Asselin, A. Eur. J. Med. Chem. 1990, 25, 191.
19. For methylindoles 5, 7, and 11, see: ref 8. For indole 6, see: ref 7. For indole 8, see: Tamura, Y. Adachi, M.; Kawasaki, T.; Yasuda, H.; Kita, Y. J. Chem. Soc., Perkin Trans. 1 1980, 1132.
20. For indole 9, see: ref 9. For indole 10, see: Kitano, M.; Kojima, A.; Nakano, K.; Miyagishi, A.; Noguchi, T.; Ohashi, N. Chem. Phar. Bull. 1999, 47, 1538.
21. A nucleophilic catalysis mechanism involving DBU was proposed for the esterification of carboxylic acid with DMC. Shieh, W.; Dell, S.; Repič, O. J. Org. Chem. 2002, 67, 2188.
22. For the hard - soft acid - base concept and definition, see: Carey, F. A.; Sundberg, R. J. Nucleophilic Substitution. In Advanced Organic Chemistry, 2nd ed.; Plenum Press: New York, 1984; Part A, Chapter 5.
23. Ho, T.-L. Hard and Soft Acids and Bases Principle in Organic Chemistry; Academic Press: New York, 1977.
24. 2: C, 76.48; H, 5.21; N, 5.57. Found: C, 77.00; H, 5.14; N, 5.55.
25. Reetz, M. T.; Hutte, S.; Goddard, R.; Minet, U. J. Chem. Soc., Chem. Commun. 1995, 275.
26. Ito, Y.; Kobayashi, K.; Seko, N.; Saegusa, T. Bull. Chem. Soc. Jpn. 1984, 57, 73.
27. Begtrup M.; Elguero, J.; Faure, R.; Camps, P.; Estopá, C.; Ilavský, D.; Fruchier, A.; Marzin, C.; Mendoza, J. Magn. Reson. Chem. 1988, 26, 134.