Synthesis of Chlorin-Fused Monospirooxindolopyrrolidines Through a Facile [3 + 2]-Cycloaddition of Azomethine Ylides

REFERENCES

• Meunier , B. Metalloporphyrins as versatile catalysts for oxidation reactions and oxidative DNA cleavage . Chem. Rev. 1992 , 92 , 1411 .
   Web of Science ®Google Scholar
• Wasielewski , M. R. Photoinduced electron transfer in supramolecular systems for artificial photosynthesis . Chem. Rev. 1992 , 92 , 435 .
   Web of Science ®Google Scholar
• Ali , H. ; Lier , J. E. Metal complexes as photo- and radiosensitizers . Chem. Rev. 1999 , 99 , 2379 .
   PubMed Web of Science ®Google Scholar
• (a) Ohkubo , K. ; Kotani , H. ; Shao , J. G. ; Ou , Z. P. ; Kadish , K. M. ; Li , G. L. ; Pandey , R. K. ; Fujitsuka , M. ; Ito , O. ; Imahori , H. ; Fukuzumi , S. Production of an ultra-long-lived charge-separated state in a zinc chlorin-C60 dyad by one-step photoinduced electron transfer . Angew. Chem. Int. Ed. 2004 , 43 , 853 ; (b) Vlassiouk , I. ; Smirnov , S. ; Kutzki , O. ; Wedel , M. ; Montforts , F. P. Radical induced impeding of charge recombination . J. Phys. Chem. B. 2002 , 106 , 8657 .
   PubMed Web of Science ®Google Scholar
• (a) Ohkubo , K. ; Kotani , H. ; Shao , J. G. ; Ou , Z. P. ; Kadish , K. M. ; Li , G. L. ; Pandey , R. K. ; Fujitsuka , M. ; Ito , O. ; Imahori , H. ; Fukuzumi , S. Small reorganization energy of intramolecular electron transfer in fullerene-based dyads with short linkage . J. Phys. Chem. A. 2002 , 106 , 10991 ; (b) Kureishi , Y. ; Tamiaki , H. ; Shiraishi , H. ; Maruyama , K. Photo-induced electron transfer from synthetic chlorophyll analogue to fullerene C60 on carbon paste electrode: Preparation of a novel solar cell . Bioelectrochem. Bioenerg. 1999 , 48 , 95 .
   Google Scholar
• (a) Lash , T. D. Modification of the porphyrin chromophore by ring fusion: Identifying trends due to annelation of the porphyrin nucleus. J. Porphyrins Phthalocyanines 2001, 5, 267; (b) Kobayashi , N. ; Konami , H. Molecular orbitals and electronic spectra of benzo-fused and related porphyrin analogues. J. Porphyrins Phthalocyanines 2001, 5, 233; (c) Kadish, K. M.; Smith, K. M.; Guilard, R.; Lash, T. D. The Porphyrin Handbook; Academic Press: San Diego, 2000; vol. 2, chap. 10, p. 125.
   Google Scholar
• (a) Ackroyd , R. ; Kelty , C. ; Brown , N. ; Reed , M. The history of photodetection and photodynamic therapy . Photochem. Photobiol. 2001 , 74 , 656 ; (b) Bonnett, R. In Chemical Aspects of Photodynamic Therapy; Gordon and Breach Science Publishers: Australia, 2000; p. 177 .
   PubMed Web of Science ®Google Scholar
• Silva , A. M. G. ; Tome , A. C. ; Neves , M. G. P. M. S. ; Silva , A. M. S. ; Caveleiro , J. A. S. ; Perrone , D. ; Dondoni , A. Porphyrins in 1,3-dipolar cycloaddition reactions with sugar nitrons: Synthesis of glycoconjugated isoxazolidine-fused chlorins and bacteriochlorins . Tetrahedron Lett. 2002 , 43 , 603 .
   Web of Science ®Google Scholar
• Silva , A. M. G. ; Tome , A. C. ; Neves , M. G. P. M. S. ; Caveleiro , J. A. S. Porphyrins in 1,3-dipolar cycloaddition reactions: Synthesis of a novel pyrazoline-fused chlorin and a pyrazole-fused porphyrin . Synlett 2002 , 1155 .
   Google Scholar
• (a) Silva , A. M. G. ; Tome , A. C. ; Neves , M. G. P. M. S. ; Caveleiro , J. A. S. ; Perrone , D. ; Dondoni , A. Porphyrins in 1,3-dipolar cycloadditions with sugar azomethine ylides: Synthesis of pyrrolidinoporphyrin glycoconjugates . Synlett 2005 , 857 ; (b) Liu , X. G. ; Feng , Y. Q. ; Tan , C. J. ; Chen , H. L. Cycloaddition of porphyrins to isatin: Synthesis of novel spiro porphyrin derivatives . Synth. Commun. 2006 , 36 , 2655 .
   Google Scholar
• Flemming , J. ; Dolphin , D. Carbonyl ylide 1,3-dipolar cycloadditions with porphyrins . Tetrahedron Lett. 2002 , 43 , 7281 .
   Google Scholar
• Liu , X. G. ; Feng , Y. Q. ; Chen , X. ; Li , F. ; Li , X. G. Porphyrins as dipolarophiles in 1,3-dipolar cycloaddition reactions with nitrile oxide . Synlett 2005 , 1030 .
   Google Scholar