Efficient Synthesis of Substituted Polyarylphthalimides via Cycloaddition of Cyclopentadienones with 2-Bromomaleimide

Abstract

Functionalized tetraarylphthalimides or diarylphthal­imides fused with an acenaphthene moiety have been prepared in one step from 2-bromomaleimide and tetraarylcyclopentadienones (tetracyclones) or 7,9-diaryl-8H-cyclopentacenaphthylene-8-ones (acecyclones). The reaction, involving a cycloaddition-decarbonylation-dehydrobromination sequence, gives high isolated yields and is compatible with the presence of various functional groups.

arenes - cyclopentadienones - Diels-Alder reaction - elimination - imides

References and Notes

1a Coseri S. Catal. Rev.  2009,  51:  218 

1b Recupero F. Punta C. Chem. Rev.  2007,  107:  3800 

1c Ishii Y. Sakaguchi S. Catal. Today  2006,  117:  105 

1d Sheldon RA. Arends IWCE. J. Mol. Catal. A: Chem.  2006,  251:  200 

1e Sheldon RA. Arends IWCE. Adv. Synth. Catal.  2004,  346:  1051 

1f Minisci F. Recupero F. Pedulli GF. Lucarini M. J. Mol. Catal. A: Chem.  2003,  204-205:  63 

1g Ishii Y. Sakaguchi S. Iwahama T. Adv. Synth. Catal.  2001,  343:  393 

2a Shen J. Tan C.-H. Org. Biomol. Chem.  2008,  6:  4096 

2b Zhang Q. Chen C. Ma H. Miao H. Zhang W. Sun Z. Xu J. J. Chem. Technol. Biotechnol.  2008,  83:  1364 

2c Wang J.-R. Liu L. Wang Y.-F. Zhang Y. Deng W. Guo Q.-X. Tetrahedron Lett.  2005,  46:  4647 

2d Saha B. Koshino N. Espenson JH. J. Phys. Chem. A  2004,  108:  425 

2e Sawatari N. Sakaguchi S. Ishii Y. Tetrahedron Lett.  2003,  44:  2053 

2f Shibamoto A. Sakaguchi S. Ishii Y. Tetrahedron Lett.  2002,  43:  8859 

2g Sawatari N. Yokota T. Sakaguchi S. Ishii Y. J. Org. Chem.  2001,  66:  7889 

2h Wentzel BB. Donners MPJ. Alsters PL. Feiters MC. Nolte RJM. Tetrahedron  2000,  56:  7797 

2i Gorgy K. Lepretre J.-C. Saint-Aman E. Einhorn C. Einhorn J. Marcadal C. Pierre J.-L. Electrochim. Acta  1998,  44:  385 

For examples of chiral analogues of NHPI, see:

2j Shen J. Tan C.-H. Org. Biomol. Chem.  2008,  6:  4096 

2k Nechab M. Kumar DN. Philouze C. Einhorn C. Einhorn J. Angew. Chem. Int. Ed.  2007,  46:  3080 

2l Einhorn C. Einhorn J. Marcadal-Abbadi C. Pierre J.-L. J. Org. Chem.  1999,  64:  4542 

3 Nechab M. Einhorn C. Einhorn J. Chem. Commun.  2004,  1500 

4 Sun Y. Zhang W. Hu X. Li H. J. Phys. Chem. B  2010,  114:  4862 

5 Ogliaruso MA. Romanelli MG. Becker EI. Chem. Rev.  1965,  65:  261 

6 For the synthesis of functionalized dibenzylketones and of the corresponding tetracyclones, see: Potter RG. Hughes TS. J. Org. Chem.  2007,  73:  2995 

7 For recent examples, see: Hapke M. Gutnov A. Weding N. Anke Spannenberg A. Fischer C. Benkhäuser-Schunk C. Heller B. Eur. J. Org. Chem.  2010,  509 ; and references cited therein

8 Alvarez LX. Bessières B. Einhorn J. Synlett  2008,  1676 

9 Einhorn C. Einhorn J. Marcadal-Abbadi C. Pierre J.-L. Synth. Commun.  2001,  31:  741 

10a Muranaka A. Matsushita O. Numao M. Kobayashi Y. Kobayashi N. Tetrahedron Lett.  2008,  49:  1856 

10b Harris FW. Norris SO. J. Heterocycl. Chem.  1972,  9:  1251 

11 Qiao X. Pelczer I. Pascal RA. Chirality  1998,  10:  154 

12

Succinimide has also been evidenced in the reaction mixture and thus aromatization may be attributed, at least partly, to a hydrogen transfer from the dihydro intermediate to maleimide.

A similar strategy has already been reported to obtain tetraarylphthalic anhydrides from tetracyclones and 2-chloromaleic anhydride, see:

13a Coan SB. Trucker DE. Becker EI. J. Am. Chem. Soc.  1955,  77:  60 

13b Shapiro EL. Becker EI. J. Am. Chem. Soc.  1953,  75:  4769 

14 Tedaldi LM. Smith MEB. Nathani RI. Baker JR. Chem. Commun.  2009,  6583 

15 Mukherjee S. Corey EJ. Org. Lett.  2010,  12:  632