Preparation of Substituted Hydroquinones and Benzofurans from 1,4-Quinone Monoketals

Xavier J. Salom-Roig; Philippe Renaud

doi:10.1055/s-2006-950236

PAPER

Preparation of Substituted Hydroquinones and Benzofurans from 1,4-Quinone Monoketals

Xavier J. Salom-Roig^a, Philippe Renaud*^b
^a LAPP, UMR 5810, Université de Montpellier II, CC 19, Place Eugène Bataillon, 34095 Montpellier Cedex 5, France
^b University of Bern, Department of Chemistry and Biochemistry, Freiestraße 3, 3012 Bern, Switzerland
e-Mail: philippe.renaud@ioc.unibe.ch;

Abstract

Alle Artikel dieser Rubrik

Abstract

An easy procedure for the preparation of 2-substituted hydroquinones, by addition of organolithium or organomagnesium compounds to 1,4-quinone monoketals followed by acid-catalyzed dienone-phenol type rearrangement, is described. Transformation of the propargylated derivatives to benzofurans is also reported.

Key words

phenols - quinones - organometallic reagents - rearrangements - heterocycles

Volltext

Referenzen

References

1a Patil AD. Freyer AJ. Killmer L. Offen P. Carte B. Jurewicz AJ. Johnson RK. Tetrahedron 1997, 53: 5047

1b Hallock YF. Cardellina JH. Boyd MR. Nat. Prod. Lett. 1998, 11: 153

1,2-Addition to quinone monoketal has been reported:

2a Swenton JS. Bradin D. Gates BD. J. Org. Chem. 1991, 56: 6156

2b McKillop A. Taylor RJK. Watson RJ. Lewis N. J. Chem. Soc., Chem. Commun. 1992, 1589

2c Trân-Huu-Dâu ME. Wartchow R. Winterfeldt E. Wong YS. Chem. Eur. J. 2001, 7: 2349

The same products are also available by anodic oxidation of 4-substituted aromatic ethers. For review articles, see:

2d Swenton JS. Acc. Chem. Res. 1983, 16: 74

2e Swenton JS. In The Chemistry of Quinonoid Compounds Vol. 2, Part 2: Patai S. Rappoport Z. John Wiley; New York: 1988. p.899

3a Stern AJ. Swenton JS. J. Org. Chem. 1988, 53: 2465

3b Stern AJ. Rohde JJ. Swenton JS. J. Org. Chem. 1989, 54: 4413

3c Swenton JS. Callinan A. Wang S. J. Org. Chem. 1992, 57: 78

3d Swenton JS. Carpenter K. Chen Y. Kerns ML. Morrow GW. J. Org. Chem. 1993, 58: 3308

3e Swenton JS. Callinan A. Chen Y. Rohde JJ. Kerns ML. Morrow GW. J. Org. Chem. 1996, 61: 1267

3f Carreño MC. Pérez González M. Fischer J. Tetrahedron Lett. 1995, 36: 4893

3g Marks TM. Morrow GW. Tetrahedron Lett. 1992, 33: 2269

3h Evans DA. Cain PA. Wong RY. J. Am. Chem. Soc. 1977, 99: 7083

3i Parker KA. Coburn CA. J. Am. Chem. Soc. 1991, 113: 8516

3j Parker KA. Su DS. J. Org. Chem. 1996, 61: 2191

The dienone-phenol rearrangement of p-quinols has been described before:

4a Guildford AJ. Turner RW. Synthesis 1982, 46

4b Ward RS. Pelter A. Abd-El-Ghani A. Tetrahedron 1996, 52: 1303

4c Ward RS. Pelter A. Abd-El-Ghani A. J. Chem. Soc., Perkin Trans. 1 1992, 2249

4d Pelter A. Ward RS. Abd-El-Ghani A. J. Chem. Soc., Perkin Trans. 1 1996, 1353

To the best of our knowledge, only two examples concerning 1,2-migrations in p-quinol ketals have been reported. Alkenyl shift:

4e Parker KA. Coburn CA. Koh Y. J. Org. Chem. 1995, 60: 2938

Phenyl shift:

4f Morrow GW. Marks TM. Sear DL. Tetrahedron 1995, 51: 10115

5

See reference 2c for the preparation of 1.

6 Kinugasa M. Harada T. Oku A. J. Org. Chem. 1996, 61: 6772

7 For a review on the preparation of benzofurans, see: Dell CP. Fused Five-Membered Hetarenes with One Heteroatom, In Science of Synthesis Vol. 10: Thomas J. Georg Thieme Verlag; Stuttgart: 2000. p.11

8 Pelter A. Elgendy SMA. J. Chem. Soc., Perkin Trans. 1 1993, 1891