New Ring Expansion of Cyclobutanones: Synthesis of Pyrrolinones, ­Pyrrolidines and Pyrroles

Guido Verniest; Stefaan Boterberg; Filip Bombeke; Christian V. Stevens; Norbert De Kimpe

doi:10.1055/s-2004-822900

LETTER

New Ring Expansion of Cyclobutanones: Synthesis of Pyrrolinones, Pyrrolidines and Pyrroles

Guido Verniest, Stefaan Boterberg, Filip Bombeke, Christian V. Stevens, Norbert De Kimpe*
Department of Organic Chemistry, Faculty of Agricultural and Applied Biological Sciences, Ghent University, Coupure Links 653, 9000 Gent, Belgium
Fax: +32(9)2646243; e-Mail: norbert.dekimpe@UGent.be;

Abstract

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Abstract

2,2-Dichlorocyclobutanones reacted with various amines to give ring opening leading to 4,4-dichlorobutanamides. These compounds proved to be suitable substrates for the synthesis of 3-pyrrolin-2-ones, 2-pyrrolidinones, pyrrolidines and pyrroles.

Key words

cyclobutanones - ring opening - ring expansion - pyrroles - heterocycles

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References

1a Bellus D. Ernst B. Angew. Chem., Int. Ed. Engl. 1988, 27: 797

1b Nemoto H. Fukumoto K. Synlett 1996, 863

2a Conia JM. Salaun JR. Acc. Chem. Res. 1972, 5: 33

2b Cagnon JR. Marchand-Brynaert J. Ghosez L. J. Braz. Chem. Soc. 1996, 7: 371

2c Mazzini C. Lebreton J. Alphand V. Furstoss R. Tetrahedron Lett. 1997, 38: 1195

2d Declair P. Kanazawa AM. de Azevedo MBM. Greene AE. Tetrahedron: Asymmetry 1996, 7: 2707 ; and references cited therein

2e Reeder LM. Hegedus LS. J. Org. Chem. 1999, 64: 3306

2f Brown RCD. Keily J. Karim R. Tetrahedron Lett. 2000, 41: 3247

3a Honda T. Kimura N. Sato S. Kato D. Tominaga H. J. Chem. Soc., Perkin Trans. 1 1994, 1043

3b de Mattos MCS. Kover WB. Synth. Commun. 1993, 23: 2895 ; Chem. Abstr. 1993, 120, 164515

3c Murta MM. de Azevedo MBM. Greene AE. J. Org. Chem. 1993, 58: 7537

3d Doherty AM. Ley SV. Tetrahedron Lett. 1986, 27: 105

3e Lopp M. Paju A. Kanger T. Pehk T. Tetrahedron Lett. 1996, 37: 7583 ; and references cited therein

3f Krief A. Ronvaux A. Tuch A. Tetrahedron 1998, 54: 6903

4a Desai P. Schildknegt K. Agrios KA. Mossman C. Milligan GL. Aubé J. J. Am. Chem. Soc. 2000, 122: 7226

4b Gracias V. Frank KE. Milligan GL. Aubé J. Tetrahedron 1997, 53: 16241

4c Furness K. Aubé J. Org. Lett. 1999, 1: 495

4d Kanazawa A. Gillet S. Declair P. Greene AE. J. Org. Chem. 1998, 63: 4660

4e Nebois P. Greene AE. J. Org. Chem. 1996, 61: 5210

4f Hoffman RV. Salvador JM. Tetrahedron Lett. 1989, 30: 4207

5a Guo Z, Cheng G, Chu F, Yang G, and Xu B. inventors; US Patent Coden CNXXEV CN 1318541. ; Chem. Abstr. 2001, 138, 73171

5b Bosch J. Roca T. Calina J.-L. Llorens O. Perez J.-J. Lagunas C. Fernandez AG. Miguel I. Fernandez-Serrat A. Farrerous C. Bioorg. Med. Chem. Lett. 2000, 10: 1745

6 Cohnen E. inventors; Brit. UK Patent Coden BAXXDU GB 2027694. ; Chem. Abstr. 1980, 94, 47121

7 Lampe JW. Chou YL. Hanna RG. Di Meo SV. Erhardt PW. Hagedorn AA. Ingebretsen WR. Cantor E. J. Med. Chem. 1993, 36: 1041

8a Lesnikova ET. Miftakhov MS. Tolstikov GA. Zh. Org. Khim. 1986, 22: 2100 ; Chem. Abstr. 1987, 107, 115396

8b Roedig A. Ganns EM. Liebigs Ann. Chem. 1982, 3: 406

8c Bigg MG. Roberts SM. Suschitzky H. J. Chem. Soc., Perkin Trans. 1 1981, 3: 926

8d Brook PR. Duke AJ. J. Chem. Soc. 1971, 10: 1764

9 Yoon CH. Nagle A. Chen C. Gandhi D. Jung KW. Org. Lett. 2003, 5: 2259

10 Sonesson C. Wikström H. Smith MW. Svensson K. Carlsson A. Waters N. Bioorg. Med. Chem. Lett. 1997, 7: 241

11a Arima K. Imanama H. Kousaka M. Tamura G. J. Antibiotics 1965, 18: 201

11b Di Santo R. Costi R. Artico M. Massa S. Lampis G. Deidda D. Pompei R. Bioorg. Med. Chem. Lett. 1998, 8: 2931

12 Chaumeil H. LeDrian C. Helv. Chim. Acta 1996, 79: 1075

13 Krepski LR. Hassner A. J. Org. Chem. 1978, 43: 2879

14 Dehmlow EV. Bueker S. Chem. Ber. 1993, 126: 2759

15 Verniest G. De Kimpe N. Synlett 2003, 2013

16 Lutz GP. Du H. Gallagher DJ. Beak P. J. Org. Chem. 1996, 61: 4542

17a Ide J. Yura Y. Bull. Chem. Soc. Jpn. 1976, 49: 3341

17b Kagabu S. Ito C. Biosci., Biotechnol., Biochem. 1992, 56: 1164

18 Maillard J, Vo Van T, Legeai J, and Benharkate M. inventors; Fr. Patent Coden FRXXBL FR 2540109 A1 19840803. ; Chem. Abstr. 1984, 102, 45770

19 Tsuge O. Kanemasa S. Hatada A. Matsuda K. Bull. Chem. Soc. Jpn. 1986, 59: 2537

20 Sonesson C. Wikström H. Smith MW. Svensson K. Carlsson A. Waters N. Bioorg. Med. Chem. Lett. 1997, 7: 241

21 Bettoni G. Cellucci C. Trotorella V. J. Heterocycl. Chem. 1976, 13: 1053

22 Mendez JM. Flores B. Léon F. Martinez ME. Vazquez A. Garcia GA. Salmon M. Tetrahedron Lett. 1996, 37: 4099

23 Campi EM. Fallon GD. Jackson WR. Nilsson Y. Aust. J. Chem. 1992, 45: 1167

New Ring Expansion of Cyclobutanones: Synthesis of Pyrrolinones, ­Pyrrolidines and Pyrroles

New Ring Expansion of Cyclobutanones: Synthesis of Pyrrolinones, Pyrrolidines and Pyrroles