Reaction of Diaryl-1,2-diones
with Homophthalic Anhydride: Efficient Formation of Isobenzofuranone
Derivatives

Vijay Nair; Rony Rajan Paul; Eringathodi Suresh

doi:10.1055/s-0030-1258216

PAPER

Reaction of Diaryl-1,2-diones with Homophthalic Anhydride: Efficient Formation of Isobenzofuranone Derivatives

Vijay Nair*^a, Rony Rajan Paul^a, Eringathodi Suresh^b
^a Organic Chemistry Section, National Institute for Interdisciplinary Science and Technology (CSIR), Trivandrum 695019, India
Fax: +91(471)2491712; e-Mail: vijaynair_2001@yahoo.com;
^b Analytical Science Discipline, Central Salt and Marine Research Institute, Bhavnagar 364002, India

Abstract

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Abstract

The reactions of homophthalic anhydride with benzils afford isobenzofuranone derivatives.

Key words

homophthalic anhydride - benzil - heterocycles - ring contraction - esterification

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References

1 von Liebig J. Ann. Chem. 1838, 25: 1

2 For a review on benzilic acid rearrangement, see: Gill GB. Comprehensive Organic Synthesis Vol. 3: Trost BM. Fleming I. Pergamon; Oxford: 1991. p.821

3a Cheeseman GWH. Werstiuk ESG. Adv. Heterocycl. Chem. 1978, 22: 367

3b Sakata G. Makino K. Kurasama Y. Heterocycles 1988, 27: 2481

3c Porter AEA. Comprehensive Heterocyclic Chemistry Part 2B, Vol. 3: Katrizky AR. Rees CW. Pergamon; Oxford: 1984. p.157

3d Brown DJ. Quinoxalines: Supplement II, In The Chemistry of Heterocyclic Compounds Taylor EC. Wipf P. John Wiley & Sons; New Jersey: 2004.

4a Nair V. Pillai AN. Menon RS. Suresh E. Org. Lett. 2005, 7: 1189

4b Pillai AN. Suresh CH. Nair V. Chem. Eur. J. 2008, 14: 5851

4c Nair V. Vellalath S. Poonoth M. Suresh E. Viji S. Synthesis 2007, 3195

4d Nair V. Mathew SC. Biju AT. Suresh E. Synthesis 2008, 1078

5a Nair V. Kumar S. Synlett 1996, 1143

5b Nair V. Sheela KC. Radhakrishnan KV. Rajesh C. Treesa PM. J. Heterocycl. Chem. 2000, 37: 659

5c Thomas A. Anilkumar G. Nair V. Tetrahedron 1996, 52: 2481

5d Nair V. Sethumadhavan D. Nair SM. Rath NP. Eigendorf GK. J. Org. Chem. 2002, 67: 7533

5e Nair V. Radhakrishnan KV. Nair AG. Bhadbhade MM. Tetrahedron Lett. 1996, 37: 5623

5f Nair V. Radhakrishnan KV. Sheela KC. Rath NP. Tetrahedron 1999, 55: 14199

6a Yu N. Poulain R. Tartar A. Gesquiere J.-C. Tetrahedron 1999, 55: 13735

6b Tamura Y. Wada A. Sasho M. Kita Y. Tetrahedron Lett. 1981, 22: 4283

6c Ramesh NG. Iio K. Okajima A. Akai S. Kita Y. Chem. Commun. 1998, 2741

6d Cushman M. Gentry J. Dekow FW. J. Org. Chem. 1977, 42: 1111

6e Cushman M. Choong TC. Valko JT. Koleck MP. J. Org. Chem. 1980, 45: 5067

6f Kita Y. Okunaka R. Honda T. Shindo M. Taniguchi M. Kondo M. Sasho M. J. Org. Chem. 1991, 56: 119

7 Tamura Y. Sasho M. Akai S. Wada A. Kita Y. Tetrahedron 1984, 40: 4539

8a Takahashi M. Shinoda T. Osada H. Nakajima T. Bull. Chem. Soc. Jpn 1975, 48: 2915

8b Wakchaure PB. Easwar S. Argade NP. Synthesis 2009, 1667

8c Stanoeva E. Haimova M. Ognyanov V. Liebigs Ann. Chem. 1984, 389

9a Nozawa K. Yamada M. Tsuda Y. Kawai K. Nakajima S. Chem. Pharm. Bull. 1981, 29: 3486

9b Vara V. Bello T. Albada E. Arrieta A. Pizzaro JL. Arriortua MI. Lopez X. Cossio FP. Org. Lett. 2008, 10: 4759

For the synthesis and applications of substituted maleic anhydride, see:

10a Kar A. Argade NP. Tetrahedron 2003, 59: 2991

10b Mhaske SB. Argade NP. J. Org. Chem. 2001, 66: 9038

10c Adlington RM. Baldwin JE. Cox RJ. Pritchard GJ. Synlett 2002, 820