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Synthesis 2007(4): 529-540
DOI: 10.1055/s-2007-965896
DOI: 10.1055/s-2007-965896
PAPER
© Georg Thieme Verlag Stuttgart · New York
Palladium-Catalyzed Intramolecular Arylation of N-Benzyl-2-iodoimidazoles: A Facile and Rapid Access to 5H-Imidazo[2,1-a]isoindoles
Further Information
Received
15 September 2006
Publication Date:
18 January 2007 (online)
Publication History
Publication Date:
18 January 2007 (online)
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
- 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