Photocyclization of N,N-phthaloylanthranilic amides coupled to ω-amino acids with increasing chain lengths

Photochemical and Photobiological Sciences

Volumn 1, Issue 4, 2002, Pages 237-239

  Griesbeck, Axel G ^a   Kramer, Wolfgang ^a   Heinrich, Thomas ^a   Lex, Johann ^a  

^a Institute of Organic Chemistry   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; ANTHRANILIC ACID DERIVATIVE; OMEGA AMINO ACID; SINGLE HETEROCYCLIC RINGS; AMINO ACID; ANTHRANILIC ACID;

ARTICLE; CHEMICAL MODEL; CHEMICAL STRUCTURE; CYCLIZATION; DECARBOXYLATION; ELECTRON; ELECTRON TRANSPORT; HYDROGEN BOND; PHOTOCHEMISTRY; PRIORITY JOURNAL; QUANTUM YIELD; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS; X RAY ANALYSIS; X RAY CRYSTALLOGRAPHY; X RAY PHOTOELECTRON SPECTROSCOPY; CHEMISTRY;

AMIDES; AMINO ACIDS; ANTHRANILIC ACIDS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PHOTOCHEMISTRY;

EID: 0036556875     PISSN: 1474905X     EISSN: None     Source Type: Journal    
DOI: 10.1039/b200448h     Document Type: Article

References (13)

1. A. G. Griesbeck, A. Henz, W. Kramer, J. Lex, F. Nerowski, M. Oelgemöller, K. Peters and E.-M. Peters, Synthesis of medium- and large-ring compounds initiated by photochemical decarboxylation of ω-phthalimidoalkanoates, Helv. Chim. Acta, 1997, 80, 912.
2. H. Görner, A. G. Griesbeck, T. Heinrich, W. Kramer and M. Oelgemöller, Time-resolved spectroscopy of sulfur- and carboxy-substituted N-alkylphthalimides, Chem. Eur. J., 2001, 7, 1530;
3. H. Görner, M. Oelgemöller and A. G. Griesbeck, Photodecarboxylation study of carboxy-substituted N-alkylphthalimides in aqueous solution: time resolved UV-Vis spectroscopy and conductometry, J. Phys. Chem. A, 2002, 106, 1458.
4. A. G. Griesbeck, F. Nerowski and J. Lex, Decarboxylative photocyclization: synthesis of benzopyrrolizidines and macrocyclic lactones, J. Org. Chem., 1999, 64, 5213.
5. A. G. Griesbeck, W. Kramer and J. Lex, Stereoselective synthesis of 1,4-benzodiazepines via photoinduced decarboxylation of N-phthaloylanthranilic acid amides, Synthesis, 2001, 35, 1159;
6. A. G. Griesbeck, W. Kramer and J. Lex, Diastereo- and enantioselective synthesis of pyrrolo[1,4]benzodiazepines through decarboxylative photocyclization, Angew. Chem., Int. Ed., 2001, 40, 577;
7. A. G. Griesbeck, W. Kramer, A. Bartoschek and H. Schimickler, Photocyclization of 2-azabicyclo[3.3.0]octane-3-carboxylate derivatives: Induced and noninduced diastereoselectivity, Org. Lett., 2001, 3, 537.
8. 4) and evaporation of the organic solvents, the residue was directly used for the terminal step.
9. 4) and evaporation of the organic solvents, the residue was purified by flash chromatography. For analytical data see Table 1.
10. A. G. Griesbeck, W. Kramer and M. Oelgemöller, Photoinduced decarboxylation reactions: Radical chemistry in water, Green Chem., 1999, 1, 205.
11. Intramolecular hydrogen bonding was detected for ω-phthalimido carboxylates: M. Oelgemöller, A. G. Griesbeck, J. Lex, A. Haeuseler, M. Schmittel, M. Niki, D. Hesek and Y. Inoue, Structural, CV and IR spectroscopic evidences for preorientation in PET-active phthalimido carboxylic acids, Org. Lett., 2001, 3, 1593;
12. M. Oelgemöller, A. Haeuseler, M. Schmittel, A. G. Griesbeck, J. Lex and Y. Inoue, Hydrogen bonding in phthalimido carboxylic acids: cyclic voltammetric study and correlation with photochemical reactivity. Part 2. Aliphatic and aromatic acids, J. Chem. Soc., Perkin Trans. 2, 2002, 676.
13. A. G. Griesbeck, T. Heinrich, M. Oelgemöller, J. Lex and A. Molis, unpublished results.