Unusual dimerization of N-protected bromomethylindoles/benzyl bromide with arylmetal halides: generation of indolylmethyl/benzyl radical

Tetrahedron

Volumn 64, Issue 9, 2008, Pages 2071-2079

  Ramesh, Neelamegam ^a   Prakash, Chandran ^a   Sureshbabu, Radhakrishnan ^a   Dhayalan, Vasudevan ^a   Mohanakrishnan, Arasambattu K ^a  

^a UNIVERSITY OF MADRAS   (India)

Author keywords

Alkyl aryl Grignard; Benzylbromide; Bromomethylindole; Indolylmethyl benzyl radical

Indexed keywords

1,2 BIS (1 PHENYLSULFONYL) 3 (METHYL) 1H INDOL 2 YLETHANE; 1,2 BIS(1 BENZOYL) 1H INDOL 2 YLETHANE; 1,2 BIS(1 PHENYLSULFONYL) 1H INDOL 4 YLETHANE; 1,2 BIS(1 PHENYLSULFONYL) 3 (BROMO) 1H INDOL 2 YLETHANE; 1,2 BIS(1 PHENYLSULFONYL) 3 (CYANO) 1H INDOL 2 YLETHANE; 1,2 BIS(1 PHENYLSULFONYL) 3 (PHENYLTHIO) 1H INDOL 2 YLETHANE; 2 BENZYL 1 (PHENYLSULFONYL) 3 (PHENYLTHIO) 1H INDOLE; 2 PHENYLCYCLOHEX 2 ENOL; 3 BENZYL 1 (PHENYLSULFONYL) 1H INDOLE; 4 BENZYL 1 (PHENYLSULFONYL) 1H INDOLE; BENZYL BROMIDE; BROMOMETHYLINDOLE DERIVATIVE; DIETHYL 2,2' (ETHANE 1,2 DIYL)BIS[1 (PHENYLSULFONYL) 1H INDOLE 3 CARBOXYLIC ACID]; DIETHYL 2,2' (ETHANE 1,2 DIYL)BIS[5 METHOXY 1 (PHENYLSULFONYL) 1H INDOLE 3 CARBOXYLIC ACID; HALIDE; INDOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; COLUMN CHROMATOGRAPHY; DIMERIZATION; PRIORITY JOURNAL; TEMPERATURE SENSITIVITY;

EID: 38549176722     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.12.047     Document Type: Article

References (32)

1. Gribble G.W., Allen R.W., Lehoullier C.S., Eaton J., Easton N.R., Slayton R.I., and Sibi M.P. J. Org. Chem. 46 (1981) 1025-1026
2. Gribble G.W., Saulnier M.G., Sibi M.P., and Obaza-Nutaitis J.A. J. Org. Chem. 49 (1984) 4518-4523
3. Sha C.-K., and Yang J.F. Tetrahedron 48 (1992) 10645-10654
4. Nagarathnam D. Synthesis (1992) 743-745
5. Mohanakrishnan A.K., and Srinivasan P.C. J. Org. Chem. 60 (1995) 1939-1946
6. Mohanakrishnan A.K., and Srinivasan P.C. Tetrahedron Lett. 37 (1996) 2659-2662
7. Mohanakrishnan A.K., and Balamurugan R. Tetrahedron Lett. 46 (2005) 4045-4048
8. Mohanakrishnan A.K., and Ramesh N. Tetrahedron Lett. 46 (2005) 4231-4233
9. Mohanakrishnan A.K., Balamurugan R., and Ramesh N. Tetrahedron Lett. 46 (2005) 8189-8193
10. Rajeswaran W.G., and Srinivasan P.C. Synthesis (1992) 835-836
11. Rajeswaran W.G., and Srinivasan P.C. Indian J. Heterocycl. Chem. 2 (1992) 89-91
12. Mohanakrishnan A.K., Ramesh N., and Prakash C. Tetrahedron Lett. 46 (2005) 6983-6985
13. 4 at reflux.
14. 2.
15. Qian H., and Negishi E. Tetrahedron Lett. 46 (2005) 2927-2930
16. Kuno A., Saino N., Kamachi T., and Okamoto S. Tetrahedron Lett. 47 (2006) 2591-2594
17. Nakao J., Inoue R., Shinokubo H., and Oshima K. J. Org. Chem. 62 (1997) 1910-1911
18. Terao J., Saito K., Nii S., Kambe N., and Sonoda N. J. Am. Chem. Soc. 120 (1998) 11822-11823
19. Hayashi Y., Shinokubo H., and Oshima K. Tetrahedron Lett. 39 (1998) 63-66
20. Fujioka T., Nakamura T., Yorimitsu H., and Oshima K. Org. Lett. 4 (2002) 2257-2259
21. Ikeda Y., Nakamura T., Yorimitsu H., and Oshima K. J. Am. Chem. Soc. 124 (2002) 6514-6515
22. Ward H.R., Lawler R.G., and Narzilli T.A. Tetrahedron Lett. 47 (1970) 521-524
23. Maeda K., Shinokubo H., and Oshima K. J. Org. Chem. 61 (1996) 6770-6771
24. Inoue A., Shinokubo H., and Oshima K. Synlett (1999) 1582-1584
25. Inoue A., Shinokubo H., and Oshima K. Org. Lett. 2 (2000) 651-653
26. Nagarathnam D., Vedachalam M., and Srinivasan P.C. Synthesis (1983) 156-157
27. Barrero A.F., Herrador M.M., Quílez del Moral J.F., Arteaga P., Arteaga J.F., Piedra M., and Sánchez E.M. Org. Lett. 7 (2005) 2301-2304
28. Barrero A.F., Herrador M.M., Quílez del Moral J.F., Arteaga P., Akssira M., Hanbali F.E., Arteaga J.F., Diéguez H.R., and Sánchez E.M. J. Org. Chem. 72 (2007) 2251-2254
29. Yanglong Q., Guisheng L., and Huang Y.-Z. J. Organomet. Chem. 381 (1990) 29-34
30. Mandal S.K., Jana S., and Roy S.C. Tetrahedron Lett. 46 (2005) 6115-6117
31. The Aldrich Catalogue (2007-08), Sigma-Aldrich Chemicals, Bangalore, India p 329
32. 1H FTNMR Spectra. 1st ed. Vol. 2 (1993), Aldrich Chemical Company, Milwaukee, WI, USA pp 8A and 28C