-
1
-
-
33846220486
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-
For excellent reviews, see:
-
-
-
-
11
-
-
33846244837
-
-
For benzo[b]furans, see:
-
-
-
-
13
-
-
0032823767
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-
Arcadi A., Cacchi S., Fabrizi G., Marinelli F., and Moro L. Synlett (1999) 1432
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(1999)
Synlett
, pp. 1432
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Arcadi, A.1
Cacchi, S.2
Fabrizi, G.3
Marinelli, F.4
Moro, L.5
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18
-
-
0037062889
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For furopyridines, see:
-
For furopyridines, see:. Arcadi A., Cacchi S., Di Giuseppe S., Fabrizi G., and Marinelli F. Org. Lett. 4 (2002) 2409
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(2002)
Org. Lett.
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Arcadi, A.1
Cacchi, S.2
Di Giuseppe, S.3
Fabrizi, G.4
Marinelli, F.5
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19
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33646453634
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For furoquinolines, see:
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For furoquinolines, see:. Aillaud I., Bossharth E., Conreaux D., Desbordes P., Monteiro N., and Balme G. Org. Lett. 8 (2006) 1113
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(2006)
Org. Lett.
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Aillaud, I.1
Bossharth, E.2
Conreaux, D.3
Desbordes, P.4
Monteiro, N.5
Balme, G.6
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20
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0042009107
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For furopyrimidines, see:
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For furopyrimidines, see:. Rao M.S., Esho N., Sergeant C., and Roman D. J. Org. Chem. 68 (2003) 6788
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(2003)
J. Org. Chem.
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Rao, M.S.1
Esho, N.2
Sergeant, C.3
Roman, D.4
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21
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33846224104
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For indoles, see:
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23
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0038343546
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Barluenga J., Trincado M., Rubio E., and Gonzalez J.M. Angew. Chem., Int. Ed. 42 (2003) 2406
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(2003)
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Barluenga, J.1
Trincado, M.2
Rubio, E.3
Gonzalez, J.M.4
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25
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0037123652
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For isoquinolines and naphthyridines, see:
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For isoquinolines and naphthyridines, see:. Huang Q., Hunter J.A., and Larock R.C. J. Org. Chem. 67 (2002) 3437
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(2002)
J. Org. Chem.
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Huang, Q.1
Hunter, J.A.2
Larock, R.C.3
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26
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13844322287
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For isoindolinones, see:
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For isoindolinones, see:. Yao T., and Larock R.C. J. Org. Chem. 70 (2005) 1432
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(2005)
J. Org. Chem.
, vol.70
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Yao, T.1
Larock, R.C.2
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27
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33846206236
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For isochromenes, see:
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30
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33846212091
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For isocoumarins, see:
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32
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0037450954
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Rossi R., Carpita A., Bellina F., Stabile P., and Mannina L. Tetrahedron 59 (2003) 2067
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(2003)
Tetrahedron
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Rossi, R.1
Carpita, A.2
Bellina, F.3
Stabile, P.4
Mannina, L.5
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33
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2342519913
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For phosphaisocoumarins, see:
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For phosphaisocoumarins, see:. Peng A.-Y., and Ding Y.-X. Org. Lett. 6 (2004) 1119
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(2004)
Org. Lett.
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Peng, A.-Y.1
Ding, Y.-X.2
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35
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33846213358
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For other recent examples of iodonium-promoted heterocyclizations of acetylenic compounds, see:
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41
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0346363694
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For iodocyclization of sulfonamide derivatives of o-(1-alkynyl)anilines leading to 3-iodoindoles, see:
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For iodocyclization of sulfonamide derivatives of o-(1-alkynyl)anilines leading to 3-iodoindoles, see:. Amjad M., and Knight D.W. Tetrahedron Lett. 45 (2004) 539
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Pal M., Madan M., Srinivas P., Pattabiraman V.R., Kalleda S.R., Akhila V., Ramesh M., Rao Mamidi N.V.S., Casturi S.R., Malde A., Gopalakrishnan B., and Yeleswarapu K.R. J. Med. Chem. 46 (2003) 3975
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Gopalakrishnan, B.11
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and references cited therein
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Lazer E.S., Miao C.K., Cywin C.L., Sorcek R., Wong H.-C., Meng Z., Potocki I., Hoermann M., Snow R.J., Tschantz M.A., Kelly T.A., McNeil D.W., Coutts S.J., Churchill L., Graham A.G., David E., Grob P.M., Engel W., Meier H., and Trummlitz G. J. Med. Chem. 40 (1997) 980 and references cited therein
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33846215317
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Our interest stems from the fact that in 1992 one of us (MP) observed that iodocyclization of o-(1-alkynyl)benzoic acid, generated in situ under Sonogashira conditions, in the presence of ICl afforded the corresponding 3-iodo substituted ylidenephthalide, see:
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24344437318
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For a review, see:. Seki M. Synthesis (2006) 2975
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Seki, M.1
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33846242364
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Dimerization of terminal alkynes (Glaser coupling), a side reaction often observed under the Sonogashira coupling conditions, predominates in the presence of oxygen or other reagents, see for example:
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68
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19944432173
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Batsanov A.S., Collings J.C., Fairlamb I.J.S., Holland J.P., Howard J.A.K., Lin Z., Marder T.B., Parsons A.C., Ward R.M., and Zhu J. J. Org. Chem. 70 (2005) 703
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Ward, R.M.9
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70
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33846261781
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Formation of 5-10% of dimeric product was observed when arylalkynes were used. CuI in the presence of an amine base is known to have a significant role in the oxidative homocoupling of terminal acetylenes and arylalkynes perhaps due to their higher reactivity than other alkynes are prone to undergo faster oxidative homocoupling.
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-
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71
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33846203146
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note
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3 with Z=2. The intensity data have been collected on Rigaku AFC-7S diffractometer with Mercury CCD area detector using graphite monochromatic Mo Kα radiation. The structure has been solved with direct methods and refined using least squares procedure using the Crystal Structure software. The present R factors are R1=0.034 and Rw=0.42. The number of observed reflections is 3420. Crystallographic data (excluding structure factors) for 8m have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication numbers CCDC 620161.
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-
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72
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33846199778
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note
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(a) This behavior, which is not clear at this stage, perhaps could be ascribed to the structural features of the starting sulfonamide, was different from the previously reported cyclizations of the sulfoximine, which invariably led to the mixture of regioisomeric five and six-membered ring products, see Ref. 19; (b) Recently, the intramolecular cyclization of alkynylamides has been studied by Larock et al., which mainly produced isoindolin-1-ones in the presence of iodine, see Ref. 9.
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73
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33846214196
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note
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3 in acetonitrile at 25 °C for 16 h.{A figure is presented}
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