The formal [3+2+1] cyclisation of cyclopropylamines with carboxylic anhydrides: A quick access to polysubstituted 2,3,3a,4-tetrahydro-6(5H)-indolone ring systems

European Journal of Organic Chemistry

Volumn , Issue 16, 2004, Pages 3517-3525

  Larquetoux, Laurent ^a   Kowalska, Justyna A ^a,b   Six, Yvan ^a  

^a INSTITUT DE CHIMIE DES SUBSTANCES NATURELLES   (France)

^b UNIVERSITY OF LODZ   (Poland)

Author keywords

Aldol reactions; Anhydrides; Cyclopropanes; Titanium

Indexed keywords

ACID ANHYDRIDE; AMINE; CARBOXYLIC ACID DERIVATIVE; CYCLOPROPANE; CYCLOPROPANE DERIVATIVE; INDOLE DERIVATIVE; KETONE DERIVATIVE;

ACYLATION; ALDOL REACTION; ARTICLE; CYCLIZATION; DIASTEREOISOMER; HEATING; MOLECULAR DYNAMICS; MOLECULAR INTERACTION; MOLECULAR MECHANICS; POLYMERIZATION; REACTION ANALYSIS; RING OPENING; SEQUENCE ANALYSIS; SUBSTITUTION REACTION; SYSTEM ANALYSIS; TECHNIQUE;

EID: 4544356398     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200400291     Document Type: Article

References (32)

1. [1a] O. G. Kulinkovich, S. V. Sviridov, D. A. Vasilevskii, T. S. Pritytskaya, J. Org. Chem. USSR (Engl. Trans.) 1989, 25, 2027-2028.
2. [1b] O. G. Kulinkovich, S. V. Sviridov, D. A. Vasilevski, Synthesis 1991, 234.
3. Reviews: [2a] O. G. Kulinkovich, A. de Meijere, Chem. Rev. 2000, 100, 2789-2834.
4. [2b] O. G. Kulinkovich, Chem. Rev. 2003, 103, 2597-2632.
5. [2c] A. de Meijere, S. I. Kozhushkov, A. I. Savchenko, in Titanium and Zirconium in Organic Synthesis (Ed.: I. Marek), Wiley-VCH, Weinheim, 2002, pp. 390-434.
6. V. Chaplinski, A. de Meijere, Angew. Chem. Int. Ed. Engl. 1996, 35, 413-414.
7. [4a] V. Chaplinski, H. Winsel, M. Kordes, A. de Meijere, Synlett 1997, 111-114.
8. [4b] J. Lee, J. K. Cha, J. Org. Chem. 1997, 62, 1584-1585.
9. [4c] B. Cao, D. Xiao, M. M. Joullié, Org. Lett. 1999, 1, 1799-1801.
10. [4d] H. B. Lee, M. J. Sung, S. C. Blackstock, J. K. Cha, J. Am. Chem. Soc. 2001, 123, 11322-11324.
11. [4e] M. Gensini, S. I. Kozhushkov, D. S. Yufit, J. A. K. Howard, M. Es-Sayed, A. de Meijere, Eur. J. Org. Chem. 2002, 2499-2507.
12. [4f] G.-D. Tebben, K. Rauch, C. Stratmann, C. M. Williams, A. de Meijere, Org. Lett. 2003, 5, 483-485.
13. [4g] N. Ouhamou, Y. Six, Org. Biomol. Chem. 2003, 1, 3007-3009.
14. [4h] M. Gensini, A. de Meijere, Chem. Eur. J. 2004, 10, 785-790.
15. E. Vilsmaier, in The Chemistry of the Cyclopropyl Group Part 2 (Ed.: S. Patai, Z. Rappoport), John Wiley & Sons, Chichester, 1987, pp. 1341-1454.
16. See, for instance: [6a] C. Kaiser, A. Burger, L. Zirngibl, C. S. Davis, C. L. Zirkle, J. Org. Chem. 1962, 27, 768-773.
17. [6b] M. E. Kuehne, J. C. King, J. Org. Chem. 1973, 38, 304-311.
18. [6c] I. G. Bolesov, L. S. Surmina, G. M. Abramova, I. B. Avezov, Y. A. Ustynyuk, R. L. Levina, Zh. Org. Khim. 1974, 10, 2107-2113; J. Org. Chem. USSR (Engl. Trans.) 1974, 10, 2122-2128.
19. [6c] I. G. Bolesov, L. S. Surmina, G. M. Abramova, I. B. Avezov, Y. A. Ustynyuk, R. L. Levina, Zh. Org. Khim. 1974, 10, 2107-2113; J. Org. Chem. USSR (Engl. Trans.) 1974, 10, 2122-2128.
20. [6d] R. H. Rynbrandt, F. E. Dutton, C. G. Chidester, J. Am. Chem. Soc. 1976, 98, 4882-4886.
21. [6e] E. Vilsmaier, R. Dörrenbächer, L. Müller, Tetrahedron 1990, 46, 8103-8116.
22. See for instance: T. M. Harris, A. D. Webb, C. M. Harris, P. J. Wittek, T. P. Murray, J. Am. Chem. Soc. 1976, 98, 6065-6067.
23. 1H NMR spectroscopy 2D-NOESY experiment.
24. This type of regioselectivity has been observed before with other bicyclic cyclopropylamine ring cleavage reactions, see ref. [6b]
25. L. Larquetoux, Y. Six, unpublished results.
26. M. A. Battiste, J. M. Coxon, in The Chemistry of the Cyclopropyl Group Part 1 (Ed.: S. Patai, Z. Rappoport), John Wiley & Sons, Chichester, 1987, pp. 255-305.
27. Y. Six, Eur. J. Org. Chem. 2003, 1157-1171.
28. N. R. Ayyangar, A. R. Choudhary, U. R. Kalkote, A. A. Natu, Synth. Commun. 1988, 18, 2011-2016.
29. E. Falb, A. Nudelman, H. E. Gottlieb, A. Hassner, Eur. J. Org. Chem. 2000, 645-655.
30. Compound 1 has been reported before but no analytical data were given: A. J. Clark, K. Jones, C. McCarthy, J. M. D. Storey, Tetrahedron Lett. 1991, 32, 2829-2832. See also ref. [4b]
31. S. H. Szajnman, W. Yan, B. N. Bailey, R. Docampo, E. El-halem, J. B. Rodriguez, J. Med. Chem. 2000, 43, 1826-1840.
32. R. Ramachandran, R. Chiron, Y. Graff, Bull. Soc. Chim. Fr. 1972, 1031-1038.