A domino sequence consisting of insertion, coupling, isomerization, and diels-alder steps yields highly fluorescent spirocycles

Angewandte Chemie - International Edition

Volumn 44, Issue 1, 2004, Pages 153-158

  D'Souza, Daniel M ^a   Rominger, Frank ^a   Müller, Thomas J J ^a  

^a UNIVERSITY OF HEIDELBERG   (Germany)

Author keywords

C C coupling; Cycloaddition; Domino reactions; Fluorescence; Spiro compounds

Indexed keywords

ALKYNE; COPPER; HETEROCYCLIC COMPOUND; PALLADIUM; PROPANOL; PROPARGYL ALCOHOL; PROTON; UNCLASSIFIED DRUG;

ALKYNYLATION; ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL STRUCTURE; CONTROLLED STUDY; CYCLOADDITION; ELECTRON TRANSPORT; FLUORESCENCE; HECK REACTION; ISOMERIZATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION; SONOGASHIRA REACTION; STEREOSPECIFICITY; THERMODYNAMICS; X RAY CRYSTALLOGRAPHY;

EID: 11244299323     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200461489     Document Type: Article

References (29)

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16. For excellent reviews and classifications of domino reactions, see, for example, a) L. F. Tietze, J. Heterocycl. Chem. 1990, 27, 47-69; b) L. F. Tietze, U. Beifuss, Angew. Chem. 1993, 105, 137-170; Angew. Chem. Int. Ed. Engl. 1993, 32, 131-163; c) L. F. Tietze, Chem. Rev. 1996, 96, 115-136.
17. For recent reviews on transition-metal-assisted sequential transformations and domino processes, see, for example, a) G. Kirsch, S. Hesse, A. Comel, Curr. Org. Synth. 2004, 1, 47-63; b) I. Nakamura, Y. Yamamoto, Chem. Rev. 2004, 104, 2127-2198, and references therein; c) G. Balme, E. Bossharth, N. Monteiro, Eur. J. Org. Chem. 2003, 4101-4111; d) G. Battistuzzi, S. Cacchi, G. Fabrizi, Eur. J. Org. Chem. 2002, 2671-2681.
18. For recent reviews on transition-metal-assisted sequential transformations and domino processes, see, for example, a) G. Kirsch, S. Hesse, A. Comel, Curr. Org. Synth. 2004, 1, 47-63; b) I. Nakamura, Y. Yamamoto, Chem. Rev. 2004, 104, 2127-2198, and references therein; c) G. Balme, E. Bossharth, N. Monteiro, Eur. J. Org. Chem. 2003, 4101-4111; d) G. Battistuzzi, S. Cacchi, G. Fabrizi, Eur. J. Org. Chem. 2002, 2671-2681.
19. For recent reviews on transition-metal-assisted sequential transformations and domino processes, see, for example, a) G. Kirsch, S. Hesse, A. Comel, Curr. Org. Synth. 2004, 1, 47-63; b) I. Nakamura, Y. Yamamoto, Chem. Rev. 2004, 104, 2127-2198, and references therein; c) G. Balme, E. Bossharth, N. Monteiro, Eur. J. Org. Chem. 2003, 4101-4111; d) G. Battistuzzi, S. Cacchi, G. Fabrizi, Eur. J. Org. Chem. 2002, 2671-2681.
20. For recent reviews on transition-metal-assisted sequential transformations and domino processes, see, for example, a) G. Kirsch, S. Hesse, A. Comel, Curr. Org. Synth. 2004, 1, 47-63; b) I. Nakamura, Y. Yamamoto, Chem. Rev. 2004, 104, 2127-2198, and references therein; c) G. Balme, E. Bossharth, N. Monteiro, Eur. J. Org. Chem. 2003, 4101-4111; d) G. Battistuzzi, S. Cacchi, G. Fabrizi, Eur. J. Org. Chem. 2002, 2671-2681.
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24. Compound 7a (=4) was synthesized from ortho-iodophenol and the corresponding 3-phenylpropynoyl chloride. Compounds 7b (=1), 7c, and 7d were prepared according to H. Sashida, Heterocycles 1998, 48, 631-634 and S. A. Brunton, K. Jones, J. Chem. Soc. Perkin Trans. 1 2000, 763-768. The syntheses of compounds 8 were performed according to K. Brickmann, F. Hambloch, J. Suffert, R. Brückner, Liebigs Ann. 1996, 4, 457-472. The detailed protocols will be described elsewhere.
25. Compound 7a (=4) was synthesized from ortho-iodophenol and the corresponding 3-phenylpropynoyl chloride. Compounds 7b (=1), 7c, and 7d were prepared according to H. Sashida, Heterocycles 1998, 48, 631-634 and S. A. Brunton, K. Jones, J. Chem. Soc. Perkin Trans. 1 2000, 763-768. The syntheses of compounds 8 were performed according to K. Brickmann, F. Hambloch, J. Suffert, R. Brückner, Liebigs Ann. 1996, 4, 457-472. The detailed protocols will be described elsewhere.
26. Compound 7a (=4) was synthesized from ortho-iodophenol and the corresponding 3-phenylpropynoyl chloride. Compounds 7b (=1), 7c, and 7d were prepared according to H. Sashida, Heterocycles 1998, 48, 631-634 and S. A. Brunton, K. Jones, J. Chem. Soc. Perkin Trans. 1 2000, 763-768. The syntheses of compounds 8 were performed according to K. Brickmann, F. Hambloch, J. Suffert, R. Brückner, Liebigs Ann. 1996, 4, 457-472. The detailed protocols will be described elsewhere.
27. All new compounds have been fully characterized spectroscopically and have given correct elemental analysis and HRMS.
28. CCDC-246090 (9d) and CCDC-246089 (9h) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB21EZ, UK; fax: (+44)1223-336-033; or deposit@ccdc.cam.ac.uk).
29. W. A. Yee, S. J. Hug, D. S. Kliger, J. Am. Chem. Soc. 1988, 110, 2164-2169.