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Intramolecular alkyne trimerizations, with the three alkyne groups in the substrate molecule, have afforded macrocyclic products with reasonable yields. (a) Lofthagen, M.; Chadha, R.; Siegel, J. S. J. Am. Chem. Soc. 1991, 113, 8785-8790. (b) Kinoshita, H.; Shinokubo, H.; Oshima, K. J. Am. Chem. Soc. 2003, 125, 7784-7785. (c) For related examples, see: Granier, T.; Cardenas, D. J.; Echavarren, A. M. Tetrahedron Lett. 2000, 41, 6775-6779. Hansen, J.; Blake, A. J.; Li, W.-S.; Mascal, M. J. Chem. Soc., Perkin Trans. 1 1998, 3371-3376. Damrauer, R.; Hankin, J. A.; Haltiwanger, R. C. Organometallics 1991, 10, 3962-3964. Mascal, M.; Hansen, J.; Blake, A. J.; Li, W.-S. Chem. Commun. 1998, 355-356. Hubert, A. J.; Hubert, M. Tetrahedron Lett. 1966, 5779-5782. Hubert, A. J. J. Chem. Soc. (C) 1967, 6-14, 1984-1985.
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0003541639
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Intramolecular alkyne trimerizations, with the three alkyne groups in the substrate molecule, have afforded macrocyclic products with reasonable yields. (a) Lofthagen, M.; Chadha, R.; Siegel, J. S. J. Am. Chem. Soc. 1991, 113, 8785-8790. (b) Kinoshita, H.; Shinokubo, H.; Oshima, K. J. Am. Chem. Soc. 2003, 125, 7784-7785. (c) For related examples, see: Granier, T.; Cardenas, D. J.; Echavarren, A. M. Tetrahedron Lett. 2000, 41, 6775-6779. Hansen, J.; Blake, A. J.; Li, W.-S.; Mascal, M. J. Chem. Soc., Perkin Trans. 1 1998, 3371-3376. Damrauer, R.; Hankin, J. A.; Haltiwanger, R. C. Organometallics 1991, 10, 3962-3964. Mascal, M.; Hansen, J.; Blake, A. J.; Li, W.-S. Chem. Commun. 1998, 355-356. Hubert, A. J.; Hubert, M. Tetrahedron Lett. 1966, 5779-5782. Hubert, A. J. J. Chem. Soc. (C) 1967, 6-14, 1984-1985.
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(b) A discussion of these two competing reaction pathways, with their disparate requirements, appeared as early as 1935 (Spangel, E. W.; Carothers, W. H. J. Am. Chem. Soc. 1935, 57, 929-934).
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(c) Reference 19a.
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Kosak, J. R., Ed.; Marcel Dekker: New York, Chapter 2
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For reviews on heterophanes, see: (a) Newkome, G. R.; Traynham, J. G.; Baker, G. R. In Comprehensive Heterocyclic Chemistry; Lwowski, W., Ed.; Pergamon: New York, 1984; Vol. 7, Part 5, pp 763-780. (b) Newkome, G. R.; Sauer, J. D.; Roper, J. M.; Hager, D. C. Chem. Rev. 1977, 77, 513-597. For reviews on synthesis of pyridinophanes, see: (c) Shkil, G. P.; Sagitullin, R. S. Chem. Heterocycl. Compds. 1998, 34, 507-528. (d) Majestic, V. K.; Newkome, G. R. Top. Curr. Chem. 1982, 106, 79-118.
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For reviews on heterophanes, see: (a) Newkome, G. R.; Traynham, J. G.; Baker, G. R. In Comprehensive Heterocyclic Chemistry; Lwowski, W., Ed.; Pergamon: New York, 1984; Vol. 7, Part 5, pp 763-780. (b) Newkome, G. R.; Sauer, J. D.; Roper, J. M.; Hager, D. C. Chem. Rev. 1977, 77, 513-597. For reviews on synthesis of pyridinophanes, see: (c) Shkil, G. P.; Sagitullin, R. S. Chem. Heterocycl. Compds. 1998, 34, 507-528. (d) Majestic, V. K.; Newkome, G. R. Top. Curr. Chem. 1982, 106, 79-118.
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For reviews on heterophanes, see: (a) Newkome, G. R.; Traynham, J. G.; Baker, G. R. In Comprehensive Heterocyclic Chemistry; Lwowski, W., Ed.; Pergamon: New York, 1984; Vol. 7, Part 5, pp 763-780. (b) Newkome, G. R.; Sauer, J. D.; Roper, J. M.; Hager, D. C. Chem. Rev. 1977, 77, 513-597. For reviews on synthesis of pyridinophanes, see: (c) Shkil, G. P.; Sagitullin, R. S. Chem. Heterocycl. Compds. 1998, 34, 507-528. (d) Majestic, V. K.; Newkome, G. R. Top. Curr. Chem. 1982, 106, 79-118.
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For reviews on heterophanes, see: (a) Newkome, G. R.; Traynham, J. G.; Baker, G. R. In Comprehensive Heterocyclic Chemistry; Lwowski, W., Ed.; Pergamon: New York, 1984; Vol. 7, Part 5, pp 763-780. (b) Newkome, G. R.; Sauer, J. D.; Roper, J. M.; Hager, D. C. Chem. Rev. 1977, 77, 513-597. For reviews on synthesis of pyridinophanes, see: (c) Shkil, G. P.; Sagitullin, R. S. Chem. Heterocycl. Compds. 1998, 34, 507-528. (d) Majestic, V. K.; Newkome, G. R. Top. Curr. Chem. 1982, 106, 79-118.
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14944380789
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4 did not meaningfully influence the macrocyclization of diyne 8 and p-tolunitrile via a template effect.
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83
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14944367164
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2, dppe, and AgOTf. For references on diyne-nitrile cycloadditions promoted by transition metals, see ref 19a.
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85
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15 An atmosphere of CO has been shown to regenerate the active cobalt catalyst in the Pauson-Khand reaction, see: (a) Krafft, M. E.; Boñaga, L. V. R.; Hirosawa, C. J. Org. Chem. 2001, 66, 3004-3020 and references therein. (b) Park, K. H.; Jung, I. G.; Chung, Y. K. Org. Lett. 2004, 6, 1183-1186.
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15 An atmosphere of CO has been shown to regenerate the active cobalt catalyst in the Pauson-Khand reaction, see: (a) Krafft, M. E.; Boñaga, L. V. R.; Hirosawa, C. J. Org. Chem. 2001, 66, 3004-3020 and references therein. (b) Park, K. H.; Jung, I. G.; Chung, Y. K. Org. Lett. 2004, 6, 1183-1186.
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14944372666
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89
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14944366156
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note
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21a
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90
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For an example of the effect of reaction concentration on macrocyclization, see: Yamamoto, K.; Biswas, K.; Gaul, K.; Danishefsky, S. J. Tetrahedron Lett. 2003, 44, 3297-3299.
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14944346143
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note
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7g
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92
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14944349200
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note
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2, 0.005 M in DME, reflux, ca. 18 h) to obtain low yields of benzannulated products iia (25%) or iib (10%).
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96
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(c) Bönnemann, H.; Brijoux, W.; Brinkmann, R.; Meurers, W. Helv. Chim. Acta 1984, 67, 1616-1624.
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(a) Heller, B.; Sundermann, B.; Buschmann, H.; Drexler, H.-J.; You, J.; Holzgrabe, U.; Heller, E.; Oehme, G. J. Org. Chem. 2002, 67, 4414-4422. Heller, B.; Reihsig, J.; Schulz, W.; Oehme, G. Appl. Organomet. Chem. 1993, 7, 641-646.
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14944356988
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(b) cod = 1.5-cyclooctadiene.
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100
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9444268337
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14944362549
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A survey of cyanamide reactivity with diynes of varying tethered lengths in given in ref 36.
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102
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0242712787
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Aminopyridines, which are important as pharmaceutical agents, ligands in inorganic and organometallic chemistry, and fluorescent dyes, are typically prepared by the substitution of halogenated pyridines (Thomas, S.; Roberts, S.; Pasumansky, L.; Gamsey, S.; Singaram, B. Org. Lett. 2003, 5, 3867-3870 and references therein).
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For cobalt-mediated cycloaddition of alkynes with isocyanates, see: (a) Earl, R. A.; Vollhardt, K. P. C. J. Org. Chem. 1984, 49, 4786-4800. (b) Earl, R. A.; Vollhardt, K. P. C. J. Am. Chem. Soc. 1983, 105, 6991-6993. (c) Hong, P.; Yamazaki, H. Tetrahedron Lett. 1977, 1333-1336. (d) Hong, P.; Yamazaki, H. Synthesis 1977, 50-52. For nickel-mediated cycloaddition of alkynes with isocyanates, see: (e) Hoberg, H.; Oster, B. W. J. Organomet. Chem. 1983, 252, 359-364. (f) Hoberg, H.; Oster, B. W. J. Organomet. Chem. 1982, 234, C35-C38. (g) Hoberg, H.; Oster, B. W. Synthesis 1982, 324-325. For the synthesis of pyridone-containing macrocycles without using transition metals, see: (h) Bradshaw, J. S.; Nakatsuji, Y.; Huszthy, P.; Wilson, B. E.; Dalley, N. K.; Izatt, R. M. J. Heterocycl. Chem. 1986, 23, 353-360. For a recent synthesis of 2-pyridones, see: (i) Hachiya, I.; Ogura, K.; Shimizu, M. Org. Lett. 2002, 4, 2755-2757.
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For cobalt-mediated cycloaddition of alkynes with isocyanates, see: (a) Earl, R. A.; Vollhardt, K. P. C. J. Org. Chem. 1984, 49, 4786-4800. (b) Earl, R. A.; Vollhardt, K. P. C. J. Am. Chem. Soc. 1983, 105, 6991-6993. (c) Hong, P.; Yamazaki, H. Tetrahedron Lett. 1977, 1333-1336. (d) Hong, P.; Yamazaki, H. Synthesis 1977, 50-52. For nickel-mediated cycloaddition of alkynes with isocyanates, see: (e) Hoberg, H.; Oster, B. W. J. Organomet. Chem. 1983, 252, 359-364. (f) Hoberg, H.; Oster, B. W. J. Organomet. Chem. 1982, 234, C35-C38. (g) Hoberg, H.; Oster, B. W. Synthesis 1982, 324-325. For the synthesis of pyridone-containing macrocycles without using transition metals, see: (h) Bradshaw, J. S.; Nakatsuji, Y.; Huszthy, P.; Wilson, B. E.; Dalley, N. K.; Izatt, R. M. J. Heterocycl. Chem. 1986, 23, 353-360. For a recent synthesis of 2-pyridones, see: (i) Hachiya, I.; Ogura, K.; Shimizu, M. Org. Lett. 2002, 4, 2755-2757.
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For cobalt-mediated cycloaddition of alkynes with isocyanates, see: (a) Earl, R. A.; Vollhardt, K. P. C. J. Org. Chem. 1984, 49, 4786-4800. (b) Earl, R. A.; Vollhardt, K. P. C. J. Am. Chem. Soc. 1983, 105, 6991-6993. (c) Hong, P.; Yamazaki, H. Tetrahedron Lett. 1977, 1333-1336. (d) Hong, P.; Yamazaki, H. Synthesis 1977, 50-52. For nickel-mediated cycloaddition of alkynes with isocyanates, see: (e) Hoberg, H.; Oster, B. W. J. Organomet. Chem. 1983, 252, 359-364. (f) Hoberg, H.; Oster, B. W. J. Organomet. Chem. 1982, 234, C35-C38. (g) Hoberg, H.; Oster, B. W. Synthesis 1982, 324-325. For the synthesis of pyridone-containing macrocycles without using transition metals, see: (h) Bradshaw, J. S.; Nakatsuji, Y.; Huszthy, P.; Wilson, B. E.; Dalley, N. K.; Izatt, R. M. J. Heterocycl. Chem. 1986, 23, 353-360. For a recent synthesis of 2-pyridones, see: (i) Hachiya, I.; Ogura, K.; Shimizu, M. Org. Lett. 2002, 4, 2755-2757.
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For cobalt-mediated cycloaddition of alkynes with isocyanates, see: (a) Earl, R. A.; Vollhardt, K. P. C. J. Org. Chem. 1984, 49, 4786-4800. (b) Earl, R. A.; Vollhardt, K. P. C. J. Am. Chem. Soc. 1983, 105, 6991-6993. (c) Hong, P.; Yamazaki, H. Tetrahedron Lett. 1977, 1333-1336. (d) Hong, P.; Yamazaki, H. Synthesis 1977, 50-52. For nickel-mediated cycloaddition of alkynes with isocyanates, see: (e) Hoberg, H.; Oster, B. W. J. Organomet. Chem. 1983, 252, 359-364. (f) Hoberg, H.; Oster, B. W. J. Organomet. Chem. 1982, 234, C35-C38. (g) Hoberg, H.; Oster, B. W. Synthesis 1982, 324-325. For the synthesis of pyridone-containing macrocycles without using transition metals, see: (h) Bradshaw, J. S.; Nakatsuji, Y.; Huszthy, P.; Wilson, B. E.; Dalley, N. K.; Izatt, R. M. J. Heterocycl. Chem. 1986, 23, 353-360. For a recent synthesis of 2-pyridones, see: (i) Hachiya, I.; Ogura, K.; Shimizu, M. Org. Lett. 2002, 4, 2755-2757.
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For cobalt-mediated cycloaddition of alkynes with isocyanates, see: (a) Earl, R. A.; Vollhardt, K. P. C. J. Org. Chem. 1984, 49, 4786-4800. (b) Earl, R. A.; Vollhardt, K. P. C. J. Am. Chem. Soc. 1983, 105, 6991-6993. (c) Hong, P.; Yamazaki, H. Tetrahedron Lett. 1977, 1333-1336. (d) Hong, P.; Yamazaki, H. Synthesis 1977, 50-52. For nickel-mediated cycloaddition of alkynes with isocyanates, see: (e) Hoberg, H.; Oster, B. W. J. Organomet. Chem. 1983, 252, 359-364. (f) Hoberg, H.; Oster, B. W. J. Organomet. Chem. 1982, 234, C35-C38. (g) Hoberg, H.; Oster, B. W. Synthesis 1982, 324-325. For the synthesis of pyridone-containing macrocycles without using transition metals, see: (h) Bradshaw, J. S.; Nakatsuji, Y.; Huszthy, P.; Wilson, B. E.; Dalley, N. K.; Izatt, R. M. J. Heterocycl. Chem. 1986, 23, 353-360. For a recent synthesis of 2-pyridones, see: (i) Hachiya, I.; Ogura, K.; Shimizu, M. Org. Lett. 2002, 4, 2755-2757.
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For cobalt-mediated cycloaddition of alkynes with isocyanates, see: (a) Earl, R. A.; Vollhardt, K. P. C. J. Org. Chem. 1984, 49, 4786-4800. (b) Earl, R. A.; Vollhardt, K. P. C. J. Am. Chem. Soc. 1983, 105, 6991-6993. (c) Hong, P.; Yamazaki, H. Tetrahedron Lett. 1977, 1333-1336. (d) Hong, P.; Yamazaki, H. Synthesis 1977, 50-52. For nickel-mediated cycloaddition of alkynes with isocyanates, see: (e) Hoberg, H.; Oster, B. W. J. Organomet. Chem. 1983, 252, 359-364. (f) Hoberg, H.; Oster, B. W. J. Organomet. Chem. 1982, 234, C35-C38. (g) Hoberg, H.; Oster, B. W. Synthesis 1982, 324-325. For the synthesis of pyridone-containing macrocycles without using transition metals, see: (h) Bradshaw, J. S.; Nakatsuji, Y.; Huszthy, P.; Wilson, B. E.; Dalley, N. K.; Izatt, R. M. J. Heterocycl. Chem. 1986, 23, 353-360. For a recent synthesis of 2-pyridones, see: (i) Hachiya, I.; Ogura, K.; Shimizu, M. Org. Lett. 2002, 4, 2755-2757.
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84986506355
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For cobalt-mediated cycloaddition of alkynes with isocyanates, see: (a) Earl, R. A.; Vollhardt, K. P. C. J. Org. Chem. 1984, 49, 4786-4800. (b) Earl, R. A.; Vollhardt, K. P. C. J. Am. Chem. Soc. 1983, 105, 6991-6993. (c) Hong, P.; Yamazaki, H. Tetrahedron Lett. 1977, 1333-1336. (d) Hong, P.; Yamazaki, H. Synthesis 1977, 50-52. For nickel-mediated cycloaddition of alkynes with isocyanates, see: (e) Hoberg, H.; Oster, B. W. J. Organomet. Chem. 1983, 252, 359-364. (f) Hoberg, H.; Oster, B. W. J. Organomet. Chem. 1982, 234, C35-C38. (g) Hoberg, H.; Oster, B. W. Synthesis 1982, 324-325. For the synthesis of pyridone-containing macrocycles without using transition metals, see: (h) Bradshaw, J. S.; Nakatsuji, Y.; Huszthy, P.; Wilson, B. E.; Dalley, N. K.; Izatt, R. M. J. Heterocycl. Chem. 1986, 23, 353-360. For a recent synthesis of 2-pyridones, see: (i) Hachiya, I.; Ogura, K.; Shimizu, M. Org. Lett. 2002, 4, 2755-2757.
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110
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84986506355
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For cobalt-mediated cycloaddition of alkynes with isocyanates, see: (a) Earl, R. A.; Vollhardt, K. P. C. J. Org. Chem. 1984, 49, 4786-4800. (b) Earl, R. A.; Vollhardt, K. P. C. J. Am. Chem. Soc. 1983, 105, 6991-6993. (c) Hong, P.; Yamazaki, H. Tetrahedron Lett. 1977, 1333-1336. (d) Hong, P.; Yamazaki, H. Synthesis 1977, 50-52. For nickel-mediated cycloaddition of alkynes with isocyanates, see: (e) Hoberg, H.; Oster, B. W. J. Organomet. Chem. 1983, 252, 359-364. (f) Hoberg, H.; Oster, B. W. J. Organomet. Chem. 1982, 234, C35-C38. (g) Hoberg, H.; Oster, B. W. Synthesis 1982, 324-325. For the synthesis of pyridone-containing macrocycles without using transition metals, see: (h) Bradshaw, J. S.; Nakatsuji, Y.; Huszthy, P.; Wilson, B. E.; Dalley, N. K.; Izatt, R. M. J. Heterocycl. Chem. 1986, 23, 353-360. For a recent synthesis of 2-pyridones, see: (i) Hachiya, I.; Ogura, K.; Shimizu, M. Org. Lett. 2002, 4, 2755-2757.
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Wilson, B.E.4
Dalley, N.K.5
Izatt, R.M.6
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0001040952
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For cobalt-mediated cycloaddition of alkynes with isocyanates, see: (a) Earl, R. A.; Vollhardt, K. P. C. J. Org. Chem. 1984, 49, 4786-4800. (b) Earl, R. A.; Vollhardt, K. P. C. J. Am. Chem. Soc. 1983, 105, 6991-6993. (c) Hong, P.; Yamazaki, H. Tetrahedron Lett. 1977, 1333-1336. (d) Hong, P.; Yamazaki, H. Synthesis 1977, 50-52. For nickel-mediated cycloaddition of alkynes with isocyanates, see: (e) Hoberg, H.; Oster, B. W. J. Organomet. Chem. 1983, 252, 359-364. (f) Hoberg, H.; Oster, B. W. J. Organomet. Chem. 1982, 234, C35-C38. (g) Hoberg, H.; Oster, B. W. Synthesis 1982, 324-325. For the synthesis of pyridone-containing macrocycles without using transition metals, see: (h) Bradshaw, J. S.; Nakatsuji, Y.; Huszthy, P.; Wilson, B. E.; Dalley, N. K.; Izatt, R. M. J. Heterocycl. Chem. 1986, 23, 353-360. For a recent synthesis of 2-pyridones, see: (i) Hachiya, I.; Ogura, K.; Shimizu, M. Org. Lett. 2002, 4, 2755-2757.
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0347411092
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For a preliminary communication, see: Boñaga, L. V. R.; Zhang, H.-C.; Gauthier, D. A.; Reddy, I.; Maryanoff, B. E. Org. Lett. 2003, 5, 4537-4540.
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Gauthier, D.A.3
Reddy, I.4
Maryanoff, B.E.5
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note
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The larger amount of the Co(I) catalyst was used to achieve complete reactions. DME was found to be a better solvent than 1,4-dioxane.
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114
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14944367163
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note
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42a For example:
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115
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0000110406
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(a) Yamamoto, Y.; Takagishi, H.; Itoh, K. Org. Lett. 2001, 13, 2117-2119.
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Yamamoto, Y.1
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Itoh, K.3
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116
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note
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42a,b
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117
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14944354415
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note
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cod = 1,5-cyclooctadiene; Cp* = pentamethylcyclopentadienide.
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120
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33947090537
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(c) Ozaki, S. Chem. Rev. 1972, 72, 457-496.
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Chem. Rev.
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Ozaki, S.1
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note
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3.
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135
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14944363949
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ref 16b
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2/tppts: (n) ref 16b.
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136
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14944341882
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note
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15 See Supporting Information.
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137
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14944340897
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note
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Dimethyl 2,2-di(prop-2-ynyl)malonate and maleic anhydride gave no cycloadduct under these reaction conditions; mostly unreacted diyne was observed at the end of the reaction.
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139
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0345491105
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Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789.
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Phys. Rev. B
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Lee, C.1
Yang, W.2
Parr, R.G.3
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141
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0000667768
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An issue of Chem. Rev. is devoted to computational transition-metal chemistry: (a) Chem. Rev. 2000, 100, 351-818. (b) Davidson, E. R. Chem. Rev. 2000, 100, 351-352. See also ref 19.
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Chem. Rev.
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142
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0000667768
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An issue of Chem. Rev. is devoted to computational transition-metal chemistry: (a) Chem. Rev. 2000, 100, 351-818. (b) Davidson, E. R. Chem. Rev. 2000, 100, 351-352. See also ref 19.
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Chem. Rev.
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Davidson, E.R.1
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143
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14944348893
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note
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18 without the use of syringe-pump addition or high-intensity light (see equation below).
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144
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0011459001
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This conversion presumably occurs via a retrocyclization, rotation, and ring-closure sequence. (a) Ville, G.; Vollhardt, K. P. C.; Winter, M. J. J. Am. Chem. Soc. 1981, 103, 5267-5269. (b) Fritch, J. R.; Vollhardt, K. P. C. Angew. Chem., Int. Ed. Engl. 1979, 18, 9-11.
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J. Am. Chem. Soc.
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Ville, G.1
Vollhardt, K.P.C.2
Winter, M.J.3
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145
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0011459001
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This conversion presumably occurs via a retrocyclization, rotation, and ring-closure sequence. (a) Ville, G.; Vollhardt, K. P. C.; Winter, M. J. J. Am. Chem. Soc. 1981, 103, 5267-5269. (b) Fritch, J. R.; Vollhardt, K. P. C. Angew. Chem., Int. Ed. Engl. 1979, 18, 9-11.
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(1979)
Angew. Chem., Int. Ed. Engl.
, vol.18
, pp. 9-11
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Fritch, J.R.1
Vollhardt, K.P.C.2
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146
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14944343947
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note
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See the Supporting Information for general experimental methods.
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