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(a) Suzuki, D.; Urabe, H.; Sato, F. J. Am. Chem. Soc. 2001, 123, 7925.
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Suzuki, D.1
Urabe, H.2
Sato, F.3
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3
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77949780397
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JP 11263737, 1999
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The zirconium-mediated cross-cyclotrimerization of ethyl ethynyl etiler and 3-hexyne was also reported as a patent; see: (b) Takahashi, T. JP 11263737, 1999; Chem. Abstr. 1999, 131, 228541.
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(1999)
Chem. Abstr.
, vol.131
, pp. 228541
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Takahashi, T.1
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4
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0013535834
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Tsuda, T.; Kunisada, K.; Nagahama, N.; Morikawa, S.; Saegusa, T. Synth, Commun. 1989, 19, 1575.
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Synth, Commun.
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Tsuda, T.1
Kunisada, K.2
Nagahama, N.3
Morikawa, S.4
Saegusa, T.5
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5
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65749107159
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Oberg, K. M.; Lee, E. E.; Rovis, T. Tetrahedron 2009, 65, 5056.
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(2009)
Tetrahedron
, vol.65
, pp. 5056
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Oberg, K.M.1
Lee, E.E.2
Rovis, T.3
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6
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75349095927
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Very recently, the nickel-catalyzed [3 + 2 + 2] cycloaddition of ethyl cyclopropylideneacetate and alkynyl ethers was reported; see: Yamasaki, R.; Terashima, N.; Sotome, I.; Komagawa, S.; Saito, S. J. Org. Chem. 2010, 75, 480.
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(2010)
J. Org. Chem.
, vol.75
, pp. 480
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Yamasaki, R.1
Terashima, N.2
Sotome, I.3
Komagawa, S.4
Saito, S.5
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7
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0001418998
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The homo-cyclotrimerization of di-tert-butoxyacetylene was reported; see: Semmelhack, M. F.; Park, J. Organometallics 1986, 5, 2550.
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(1986)
Organometallics
, vol.5
, pp. 2550
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Semmelhack, M.F.1
Park, J.2
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8
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66149185301
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Komine, Y.; Kamisawa, A.; Tanaka, K. Org Lett. 2009, 77, 2361.
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(2009)
Org Lett.
, vol.77
, pp. 2361
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Komine, Y.1
Kamisawa, A.2
Tanaka, K.3
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10
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14544299221
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(b) Tanaka, K.; Toyoda, K.; Wada, A.; Shirasaka, K.; Hirano, M. Chem.-Eur. J. 2005, 11, 1145.
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(2005)
Chem.-Eur. J.
, vol.11
, pp. 1145
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Tanaka, K.1
Toyoda, K.2
Wada, A.3
Shirasaka, K.4
Hirano, M.5
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11
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77949817159
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Other regioisomers were generated in <5% yields. A crosscyclotrimerization product of one molecule of 3a and two molecules of 4 was not detected at all.
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Other regioisomers were generated in <5% yields. A crosscyclotrimerization product of one molecule of 3a and two molecules of 4 was not detected at all.
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12
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33644886020
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Deiters and co-workers successfully overcame the regioselectivity problem in the cobalt-catalyzed intermolecular cross-cyclotrimerization of terminal, alkynes and nitriles by employing the solid-supported reaction system; see: Senaiar, R. S.; Young, D. D.; Deiters, A. Chem. Commun. 2006, 1313.
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(2006)
Chem. Commun.
, pp. 1313
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Senaiar, R.S.1
Young, D.D.2
Deiters, A.3
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13
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0037189276
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The cobalt-catalyzed regioselective cross-cyclotrimerization of tertbutylacetylene and trimethylacetonitrile leading to 2,4,6-tri-ierf- butylpyridine was reported; see: Heller, B.; Sundermann, B.; Buschmann, H.; Drexler, H.-J.; You, J.; Holzgrabe, U.; Heller, E.; Oehme, G. J. Org. Chem. 2002, 67, 4414.
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J. Org. Chem.
, vol.67
, pp. 4414
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Heller, B.1
Sundermann, B.2
Buschmann, H.3
Drexler, H.-J.4
You, J.5
Holzgrabe, U.6
Heller, E.7
Oehme, G.8
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14
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0142258960
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The ruthenium-catalyzed regioselective cross-cyclotrimerization of methyl propiolate and electron-deficient nitriles leading to 2,3,6-trisubstituted pyridines was reported; see: (a) Varela, J. A.; Carlos, L.; Saá, C. J. Org. Chem. 2003, 68, 8595.
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(2003)
J. Org. Chem.
, vol.68
, pp. 8595
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Varela, J.A.1
Carlos, L.2
Saá, C.3
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15
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12944303660
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(b) Yamamoto, Y.; Kinpara, K.; Saigoku, T.; Takagishi, H.; Okuda, S.; Nishiyama, H.; Itoh, K. J. Am. Chem. Soc. 2005, 127, 605.
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(2005)
Am. Chem. Soc.
, vol.127
, pp. 605
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Yamamoto, Y.1
Kinpara, K.2
Saigoku, T.3
Takagishi, H.4
Okuda, S.5
Nishiyama, H.6
Itoh, K.J.7
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16
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19744370350
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For the regioselective cross-cyclotrimerization of terminal, alkynes and nitriles using a stoichiometric amount of a transition metal, see: (a) Suzuki, D.; Nobe, Y.; Watai, Y.; Tanaka, R.; Takayama, Y.; Sato, F.; Urabe, H. J. Am. Chem. Soc. 2005, 127, 7474.
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(2005)
J. Am. Chem. Soc.
, vol.127
, pp. 7474
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Suzuki, D.1
Nobe, Y.2
Watai, Y.3
Tanaka, R.4
Takayama, Y.5
Sato, F.6
Urabe, H.7
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17
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0037042297
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(b) Takahashi, T.; Tsai, F.-Y.; Li, Y.; Wang, H.; Kondo, Y.; Yamanaka, M.; Nakajima, K.; Kotora, M. J. Am. Chem. Soc. 2002, 124, 5059.
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(2002)
J. Am. Chem. Soc.
, vol.124
, pp. 5059
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Takahashi, T.1
Tsai, F.-Y.2
Li, Y.3
Wang, H.4
Kondo, Y.5
Yamanaka, M.6
Nakajima, K.7
Kotora, M.8
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18
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33748550638
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For the rhodium-catalyzed intermolecular cross-cyclotrimerization of a terminal alkyne and an activated nitrile leading to two regioisomeric pyridines, see: Tanaka, K.; Suzuki, N.; Nishida, G. Eur. J. Org. Chem. 2006, 3917.
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(2006)
Eur. J. Org. Chem.
, pp. 3917
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Tanaka, K.1
Suzuki, N.2
Nishida, G.3
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19
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27144521700
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Our research group reported the rhodium-catalyzed intermolecular cross-cyclotrimerization of terminal alkynes and isocyanates, but the regioselectivities vary depending on the alkynes used; see: Tanaka, K.; Wada, A.; Noguchi, K. Org Lett. 2005, 7, 4737.
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(2005)
Org Lett.
, vol.7
, pp. 4737
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Tanaka, K.1
Wada, A.2
Noguchi, K.3
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20
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55449099596
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For recent reviews of the transition-metal-catalyzed cyclotrimerization for the synthesis of nitrogen heterocycles, see: (a) Varela, J. A.; Saá, C. Synlett 2008, 2571.
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(2008)
Synlett
, pp. 2571
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Varela, J.A.1
Saá, C.2
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26
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77949805954
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Homo-cyclotrimerization products of 3a-e were generated as byproducts in the reactions of Tables 1-3.
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Homo-cyclotrimerization products of 3a-e were generated as byproducts in the reactions of Tables 1-3.
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27
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77949863495
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Although the slow addition of aryl ethynyl ether 3a to nitrile 6a or isocyanate 8a and the Rh catalyst over 30 min was also examined, the yields of the corresponding pyridine 7aa and 2-pyridone 9aa. were not increased.
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Although the slow addition of aryl ethynyl ether 3a to nitrile 6a or isocyanate 8a and the Rh catalyst over 30 min was also examined, the yields of the corresponding pyridine 7aa and 2-pyridone 9aa. were not increased.
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