Rh2(OAc)4-catalyzed regioselective intermolecular C-H insertion reactions: Novel synthesis of 2-pyrrol-3′-yloxindoles

Synlett

Volumn , Issue 11, 2002, Pages 1783-1786

  Muthusamy, Sengodagounder ^a   Gunanathan, Chidambaram ^a  

^a CSIR CENTRAL SALT AND MARINE CHEMICALS RESEARCH INSTITUTE   (India)

Author keywords

C H insertion reaction; Oxindole; Pyrrole; Rhodium(II) acetate

Indexed keywords

2 PYRROL 3' YLOXINDOLE DERIVATIVE; INDOLE DERIVATIVE; PYRROLE DERIVATIVE; RHODIUM COMPLEX; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL INTERACTION; CHEMICAL STRUCTURE; COLUMN CHROMATOGRAPHY; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0036422095     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2002-34889     Document Type: Article

References (37)

1. (a) Curtius, T. Berichte 1883, 16, 2230.
2. (b) Curtius, T. J. Prakt. Chem. 1888, 38, 396.
3. Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds. From Cyclopropanes to Ylides; Wiley-Interscience: New York, 1998.
4. (a) Padwa, A. J. Organomet. Chem. 2001, 617-618, 3.
5. (b) Doyle, M. P.; Forbes, D. C. Chem. Rev. 1998, 98, 911.
6. (c) Doyle, M. P.; McKervey, M. A. Chem. Commun. 1997, 983.
7. (d) Padwa, A.; Weingarten, M. D. Chem. Rev. 1996, 96, 223.
8. (e) Miller, D. J.; Moody, C. J. Tetrahedron 1995, 51, 10811.
9. (f) Padwa, A.; Austin, D. J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1797.
10. (g) Doyle, M. P. Chem. Rev. 1986, 86, 919.
11. Ye, T.; McKervey, M. A. Chem. Rev. 1994, 94, 1091.
12. (a) Doyle, M. P.; Kalinin, A. V. Tetrahedron Lett. 1996, 37, 1371.
13. (b) Bode, J. W.; Doyle, M. P.; Protopopova, M. N.; Zhou, Q. L. J. Org. Chem. 1996, 61, 9146.
14. (c) Taber, D. F.; Song, Y. J. Org. Chem. 1996, 61, 6706.
15. (d) Wee, A. G. H.; Liu, B. Tetrahedron Lett. 1996, 37, 145.
16. Muthusamy, S.; Gunanathan, C.; Babu, S. A.; Suresh, E.; Dastidar, P. Chem. Commun. 2002, 824.
17. (a) Maryanoff, B. E. J. Org. Chem. 1982, 47, 3000.
18. (b) Demonceau, A.; Noels, A. F.; Hubert, A. J.; Teyssie, P. J. Chem. Soc., Chem. Commun. 1981, 688.
19. (c) Maryanoff, B. E. J. Org. Chem. 1979, 44, 4410.
20. (d) Maryanoff, B. E. J. Heterocycl. Chem. 1977, 14, 177.
21. (a) Pirrung, M. C.; Florian, B. J. Org. Chem. 1999, 64, 3642.
22. (b) Pirrung, M. C.; Zhang, J.; McPhail, A. T. J. Org. Chem. 1991, 56, 6269.
23. (a) Muthusamy, S.; Gunanathan, C.; Babu, S. A. Synthesis 2002, 471.
24. (b) Muthusamy, S.; Babu, S. A.; Gunanathan, C.; Jasra, R. V. Synlett 2002, 407.
25. (c) Muthusamy, S.; Babu, S. A.; Gunanathan, C.; Suresh, E.; Dastidar, P. Bull. Chem. Soc. Jpn. 2002, 75, 801.
26. (d) Muthusamy, S.; Babu, S. A.; Gunanathan, C. Tetrahedron Lett. 2002, 43, 3931.
27. (e) Muthusamy, S.; Babu, S. A.; Gunanathan, C. Tetrahedron Lett. 2002, 43, 5981.
28. (f) Muthusamy, S.; Gunanathan, C.; Babu, S. A. Tetrahedron Lett. 2001, 42, 523.
29. Cava, M. P.; Little, R. L.; Naipier, D. R. J. Am. Chem. Soc. 1958, 80, 2257.
30. Heaney, H.; Ley, S. V. J. Chem. Soc., Perkin Trans 1 1973, 499.
31. General Procedure for the Synthesis of 2-Pyrroi-3′-yloxindoles: In an oven-dried flask, a solution containing 1.2 equiv of pyrrole and 1 mol% of rhodium(II) acetate dimer in 10 mL of dry dichloromethane (dried over phosphorous pentoxide) was degasified under an argon atmosphere. To this reaction mixture, a solution of 1 equiv of appropriate cyclic diazoamide in dry dichloromethane was added dropwise slowly for 1 h period under an argon atmosphere at r.t. The reaction mixture was allowed to stir and followed by TLC till the disappearance of the starting material. The solvent was removed under reduced pressure and the residue purified by flash silica gel column chromatography to afford the respective C-H insertion products.
32. 2O: C, 79.97; H, 6.71; N, 8.48. Found: C, 79.74; H, 6.69; N, 8.51.
33. (a) Bashford, K. E.; Cooper, A. L.; Kane, P. D.; Moody, C. J.; Muthusamy, S.; Swann, E. J. Chem. Soc., Perkin Trans. 1 2002, 1672.
34. (b) Bagley, M. C.; Buck, R. T.; Hind, S. L.; Moody, C. J. J. Chem. Soc., Perkin Trans. 1 1998, 591.
35. (c) Bagley, M. C.; Moody, C. J. J. Chem. Soc., Perkin Trans. 1 1998, 601.
36. (a) Hu, W.; Timmons, D. J.; Doyle, M. P. Org. Lett. 2002, 4, 901.
37. (b) Davies, H. M. L.; Townsend, R. J. J. Org. Chem. 2001, 66, 6595; and references cited therein.