Palladium-Catalyzed Intramolecular Arylation of N-Benzyl-2-iodoimidazoles: A Facile and Rapid Access to 5H-Imidazo[2,1-a]isoindoles

Renata Marcia de Figueiredo; Sylviane Thoret; Caroline Huet; Joëlle Dubois

doi:10.1055/s-2007-965896

PAPER

Palladium-Catalyzed Intramolecular Arylation of N-Benzyl-2-iodoimidazoles: A Facile and Rapid Access to 5H-Imidazo[2,1-a]isoindoles

Renata Marcia de Figueiredo, Sylviane Thoret, Caroline Huet, Joëlle Dubois*
Institut de Chimie des Substances Naturelles-CNRS, avenue de la Terrasse, 91198 Gif-sur-Yvette Cedex, France
Fax: +33(1)69077247; e-Mail: joelle.dubois@icsn.cnrs-gif.fr;

Abstract

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Abstract

The first example of a Pd-catalyzed intramolecular arylation involving the C-2 position of an imidazole ring is presented. Application of this reaction led to the formation of 5H-imidazo[2,1-a]isoindole in one step from N-benzyl-2-iodoimidazole. Microwave irradiation enhanced the rate of reaction allowing the synthesis of various imidazo[2,1-a]isoindole analogues.

Key words

diazo compounds - palladium - palladacycle - polycycles - arylation

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References

For a few examples, see:

1a Ohta S. Yamamoto T. Kawasaki I. Yamashita M. Katsuma H. Nasako R. Kobayashi K. Ogawa K. Chem. Pharm. Bull. 1992, 40: 2681

1b Ohta S. Yamamoto T. Kawasaki I. Yamashita M. Nagashima Y. Yoshikawa T. Chem. Pharm. Bull. 1994, 42: 821

1c Kawasaki I. Taguchi N. Yamashita M. Ohta S. Chem. Pharm. Bull. 1995, 45: 1393

1d Kawasaki I. Taguchi N. Yamamoto T. Yamashita M. Ohta S. Tetrahedron Lett. 1995, 36: 8251

1e Kawasaki I. Taguchi N. Youko Y. Yamashita M. Ohta S. Heterocycles 1996, 43: 1375

1f Lindel T. Hochgürtel M. J. Org. Chem. 2000, 65: 2806

1g Berrée F. Girard-Le Bleis F. Carboni B. Tetrahedron Lett. 2002, 43: 4935

2 Coutts IGC. Jieng S. Khandlewahl GD. Wood ML. J. Heterocycl. Chem. 1994, 31: 857

3a Sakamoto T. Nagata H. Kondo Y. Shiraiwata M. Yamanaka H. Chem. Pharm. Bull. 1987, 35: 823

3b Evans DA. Bach T. Angew. Chem., Int. Ed. Engl. 1993, 32: 1326

3c Nadipuram AK. David WM. Kumar D. Kerwin SM. Org. Lett. 2002, 4: 4543

4 Prasad ASB. Stevenson TM. Cittineni JR. Nyzam V. Knochel P. Tetrahedron 1997, 53: 7237

5 Allen WE. Fowler CJ. Lynch VM. Sessler JL. Chem. Eur. J. 2001, 7: 721

6a Kuroda T. Suzuki F. Tetrahedron Lett. 1991, 32: 6915

6b Huang J. Gu M. Youji Huaxue 1994, 14: 604 ; Chem. Abstr. 1995, 122, 214000

7a Aeberli P. Eden P. Gogerty JH. Houlihan WJ. Penberthy C. J. Med. Chem. 1975, 18: 177

7b Houlihan WJ. Kelly L. Pankuch J. Koletar J. Brand L. Janowsky A. Kopajtic TA. J. Med. Chem. 2002, 45: 4097

8a Sulkowski TS. inventors; US Patent 3663532. ; Chem. Abstr. 1972, 77, 88559

8b Sulkowski TS. inventors; US Patent 3994920. ; Chem. Abstr. 1977, 86, 106681

9a del Olmo E. Garcia-Armas M. Lopez-Perez JL. Ruiz G. Vargas F. Gimenez A. Deharo E. San Feliciano A. Bioorg. Med. Chem. Lett. 2001, 11: 2755

9b del Olmo E. Garcia-Armas M. Ybarra MI. Lopez JL. Oporto P. Gimenez A. Deharo E. San Feliciano A. Bioorg. Med. Chem. Lett. 2003, 13: 2769

10 Clyne MA. Aldabbagh F. Org. Biomol. Chem. 2006, 4: 268

11 Jeffery T. Tetrahedron 1996, 52: 10113

12a Larhed M. Moberg C. Hallberg A. Acc. Chem. Res. 2002, 35: 717

12b Kappe CO. Angew. Chem. Int. Ed. 2004, 46: 6250

12c de la Hoz A. Diaz-Ortiz A. Moreno A. Chem. Soc. Rev. 2005, 34: 164

13a Qajaba G. Jones GB. Tetrahedron Lett. 2000, 41: 5317

13b Qajaba G. Jones GB. J. Org. Chem. 2000, 65: 7187

13c Tan KL. Vasudevan RG. Bergman JA. Ellman AJ. Org. Lett. 2003, 5: 2131

14a Cuberes MR. Moreno-Manas M. Trius A. Synthesis 1985, 302

14b Milgrom LR. Dempsey PJF. Yahioglu G. Tetrahedron 1996, 52: 9877

14c Lee HM. Lu CY. Lin HC. Chiu PL. Cheng PY. Tetrahedron 2004, 60: 5807

14d Kamijo T. Yamamoto R. Harada H. Iizuka K. Chem. Pharm. Bull. 1983, 41: 1213

15 Kirk KL. J. Org. Chem. 1978, 43: 4381

16 Huang Q. Campo MA. Yao T. Tian Q. Larock RC. J. Org. Chem. 2004, 69: 8251

17 Tsuji J. Palladium Reagents and Catalysts. New Perspectives for the 21 ^st Century Wiley; Chichester: 2004. p.190

18a Mukhopadhyay S. Rothenberg G. Gitis D. Baidossi M. Ponde DE. Sasson Y. J. Chem. Soc., Perkin Trans. 2 2000, 1809

18b Godula K. Sezen B. Sames D. J. Am. Chem. Soc. 2005, 127: 3648

18c Campeau L.-C. Rousseaux S. Fagnou K. J. Am. Chem. Soc. 2005, 127: 18020

19a Davies DL. Donald SMA. MacGregor SA. J. Am. Chem. Soc. 2005, 127: 13754

19b Garcia-Cuadrado D. Braga AAC. Maseras F. Echavarren AM. J. Am. Chem. Soc. 2006, 128: 1066

20 Huang Q. Campo MA. Yao T. Tian Q. Larock RC. J. Org. Chem. 2004, 69: 8251

21a Beesley RM. Ingold CK. Thorpe JF. J. Chem. Soc. 1915, 107: 1080

21b Ingold CK. J. Chem. Soc. 1921, 119: 305

22a Metlesics W. Anton T. Chaykovsky M. Toome V. Sternbach LH. J. Org. Chem. 1968, 33: 2874

22b Chaykovsky M. Benjamin L. Fryer RI. Metlesics W. J. Org. Chem. 1970, 35: 1178

23a Cuberes MR. Moreno-Manas M. Trius A. Synthesis 1985, 302

23b Milgrom LR. Dempsey PJF. Yahioglu G. Tetrahedron 1996, 52: 9877

23c Lee HM. Lu CY. Lin HC. Chiu PL. Cheng PY. Tetrahedron 2004, 60: 5807

23d Kamijo T. Yamamoto R. Harada H. Iizuka K. Chem. Pharm. Bull. 1983, 41: 1213

24 Moreno-Manas M. Bassa J. Llado N. Pleixtats R. J. Heterocycl. Chem. 1990, 27: 673