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Synthesis 2010(21): 3741-3744
DOI: 10.1055/s-0030-1258216
DOI: 10.1055/s-0030-1258216
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Reaction of Diaryl-1,2-diones with Homophthalic Anhydride: Efficient Formation of Isobenzofuranone Derivatives
Further Information
Received
10 June 2010
Publication Date:
18 August 2010 (online)
Publication History
Publication Date:
18 August 2010 (online)
Abstract
The reactions of homophthalic anhydride with benzils afford isobenzofuranone derivatives.
Key words
homophthalic anhydride - benzil - heterocycles - ring contraction - esterification
- 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 CompoundsTaylor 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