Jump to ContentJump to Main Navigation
Show Summary Details
More options …

Pure and Applied Chemistry

The Scientific Journal of IUPAC

Ed. by Burrows, Hugh / Stohner, Jürgen


IMPACT FACTOR 2018: 2.350
5-year IMPACT FACTOR: 4.037

CiteScore 2018: 4.66

SCImago Journal Rank (SJR) 2018: 1.240
Source Normalized Impact per Paper (SNIP) 2018: 1.826

Online
ISSN
1365-3075
See all formats and pricing
More options …
Volume 82, Issue 7

Issues

Efficient cyclization routes to substituted heterocyclic compounds mediated by transition-metal catalysts

Janine Cossy
  • Corresponding author
  • Laboratory of Organic Chemistry, ESPCI ParisTech, CNRS, 10 rue Vauquelin 75231, Paris Cedex 05, France
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
Published Online: 2010-05-14 | DOI: https://doi.org/10.1351/PAC-CON-09-09-12

Cyclizations induced by transition metals such as palladium, platinum, gold, and ruthenium can produce functionalized heterocycles such as 3-(arylmethylene)isoindolones, γ-lactones, and unsaturated δ-lactones.

Keywords: 3-(arylmethylene)isoindolones; cyclization; heterocycles; lactones; metals; metathesis

Conference

International Conference on Organometallic Chemistry Directed Towards Organic Synthesis (OMCOS-15), International Symposium on Organometallic Chemistry Directed Toward Organic Synthesis, OMCOS, Organometallic Chemistry Directed Toward Organic Synthesis, 15th, Glasgow, UK, 2009-07-26–2009-07-31

References

  • 1a

    , N. G. Kundu, M. W. Khan. Tetrahedron56, 4777 (2000).CrossrefGoogle Scholar

  • 1b

    , A. Couture, E. Deniau, P. Grandclaudon. Tetrahedron53, 10313 (1997);CrossrefGoogle Scholar

  • 1c

    , for dihydro-analogs (3-alkylisoindolin-1-ones), see: M.-D. Chen, X. Zhou, M.-Z. He, Y.-P. Ruan, P.-Q. Huang. Tetrahedron60, 1651 (2004).CrossrefGoogle Scholar

  • 2

    For some other examples, see.Google Scholar

  • 2a

    , P. Pigeon, B. Decroix. Tetrahedron Lett.37, 7707 (1996).CrossrefGoogle Scholar

  • 2b

    , D.-C. Ha, C.-S. Ha, C.-S. Yunn, E. Yu. Tetrahedron Lett.37, 2577 (1996).CrossrefGoogle Scholar

  • 2c

    Y. Kato, M. Takemoto, K. Achiwa. Chem. Pharm. Bull.41, 2003 (1993).Google Scholar

  • 2d

    Y. Kato, H. Ebiike, K. Achiwa, N. Ashizawa, T. Kurihara, F. Kobayashi. Chem. Pharm. Bull.38, 2060 (1990).CrossrefGoogle Scholar

  • 2e

    A. M. Islam, A. M. S. Sharief, A. H. Bedair, N. E. Hammad. Egypt. J. Chem.25, 251 (1983).Google Scholar

  • 2f

    A. M. Islam, A. M. S. Sharief, A. A. El-Maghraby, A. H. Bedear. Indian J. Chem. Sect. B16, 301 (1972).Google Scholar

  • 2g

    A. Marsili, V. Scartoni. Gazz. Chem. Ital.102, 806 (1972).Google Scholar

  • 2h

    , A. Marsili, V. Scartoni. Tetrahedron Lett. 2511 (1968).CrossrefGoogle Scholar

  • 3a

    , X. Gai, R. Grigg, T. Khammaen, S. Rajviroongit, V. Sridharan, L. Zhang, S. Collard, A. Keep. Tetrahedron Lett.44, 7441 (2003).CrossrefGoogle Scholar

  • 3b

    , C. S. Cho, H. S. Shim, H.-J. Choi, T.-J. Kim, S. C. Shim. Synth. Commun.32, 1821 (2002).CrossrefGoogle Scholar

  • 4a

    , N. G. Kundu, M. W. Khan, R. Mukhopadhyay. Tetrahedron55, 12361 (1999).CrossrefGoogle Scholar

  • 4b

    , H. Sashida, A. Kawamukai. Synthesis 1145 (1999).CrossrefGoogle Scholar

  • 4c

    , N. G. Kundu, M. W. Khan. Tetrahedron Lett.38, 6937 (1997).CrossrefGoogle Scholar

  • 5a

    , V. Rys, A. Couture, E. Deniau, P. Grandclaudon. Tetrahedron59, 6615 (2003).CrossrefGoogle Scholar

  • 5b

    , A. Couture, E. Deniau, P. Grandclaudon, C. Hoarau, V. Rys. Tetrahedron Lett.43, 2207 (2002).CrossrefGoogle Scholar

  • 5c

    , A. Couture, E. Deniau, P. Grandclaudon, H. Rybalko-Rosen, S. Léonce, B. Pfeiffer, P. Renard. Biorg. Med. Chem. Lett.12, 3557 (2002).CrossrefGoogle Scholar

  • 5d

    , A. Couture, E. Deniau, P. Grandclaudon, C. Hoarau. Tetrahedron56, 1491 (2000).CrossrefGoogle Scholar

  • 6a

    , S. Couty, B. Liégault, C. Meyer, J. Cossy. Org. Lett.6, 2511 (2004).CrossrefGoogle Scholar

  • 6b

    S. Couty, B. Liégault, C. Meyer, J. Cossy. Tetrahedron Lett.62, 3882 (2006).CrossrefGoogle Scholar

  • 7

    See references in.Google Scholar

  • 7a

    , S. Couty, C. Meyer, J. Cossy. Angew. Chem., Int. Ed.45, 6726 (2006).CrossrefGoogle Scholar

  • 7b

    , S. Couty, C. Meyer, J. Cossy. Tetrahedron65, 1809 (2009).CrossrefGoogle Scholar

  • 8a

    , F. Marion, J. Coulomb, C. Courillon, L. Fensterbank, M. Malacria. Org. Lett.6, 1509 (2004).CrossrefGoogle Scholar

  • 8b

    B. Liegault, C. Meyer, J. Cossy. Unpublished results.Google Scholar

  • 9a

    , A. Furstner, F. Stelzer, H. Szillat. J. Am. Chem. Soc.123, 11863 (2004).CrossrefGoogle Scholar

  • 9b

    , M. Mendez, M. P. Munoz, C. Nevado, D. J. Cardenas, A. M. Echavarren. J. Am. Chem. Soc.123, 10511 (2001).CrossrefGoogle Scholar

  • 9c

    , C. Nevado, L. Charruault, V. Michelet, C. Nieto-Oberhuber, M. P. Munoz, M. Mendez, M.-N. Rager, J. P. Genêt, A. M. Echavarren. Eur. J. Org. Chem. 706 (2003).CrossrefGoogle Scholar

  • 9d

    , C. Nevado, C. Ferrer, A. M. Echavarren. Org. Lett.6, 3191 (2004); for mechanistic studies, see.CrossrefGoogle Scholar

  • 9e

    , E. Soriano, P. Ballestros, J. Marco-Contelles. Organometallics24, 3172 (2005).CrossrefGoogle Scholar

  • 9f

    C. Nieto-Oberhuber, S. Lopez, M. P. Munoz, E. Bunnuel, C. Nevado, A. M. Echavarren. Angew. Chem., Int. Ed.127, 2901 (2005).Google Scholar

  • 10

    H. Hiemstra, W. N. Speckamp. In Comprehensive Organic Synthesis, Vol. 4, B. M. Trost, I. Fleming (Eds.), p. 1047, Pergamon, Oxford (1991).Google Scholar

  • 11a

    , A. Furstner, K. Langemann. J. Am. Chem. Soc.119, 9130 (1997).CrossrefGoogle Scholar

  • 11b

    , A. K. Ghosh, J. Cappiello, D. Shin. Tetrahedron Lett.39, 4651 (1998).CrossrefGoogle Scholar

  • 11c

    , J. Cossy, D. Bauer, V. Bellosta. Tetrahedron Lett.40, 4187 (1999).CrossrefGoogle Scholar

  • 11d

    , V. Boucard, G. Broustal, J. M. Campagne. Eur. J. Org. Chem. 225 (2007).CrossrefGoogle Scholar

  • 12

    , Y.-G. Wang, R. Takeyama, Y. Kobayashi. Angew. Chem., Int. Ed.45, 3320 (2006).CrossrefGoogle Scholar

  • 13

    , N. F. Langille, J. S. Panek. Org. Lett.6, 3203 (2004).CrossrefGoogle Scholar

  • 14

    K. Ono, T. Nagat, A. Nishida. Synlett 1207 (2003).Google Scholar

  • 15

    , Z.-Q. Yang, X. Geng, D. Solit, C. A. Pratilas, N. Rosen, S. J. Danishefsky. J. Am. Chem. Soc.126, 7881 (2004).CrossrefGoogle Scholar

  • 16

    , B. M. Trost, Z. T. Ball. J. Am. Chem. Soc.123, 12736 (2001).CrossrefGoogle Scholar

  • 17

    , F. Lacombe, K. Radkowski, G. Siedel, A. Furstner. Tetrahedron60, 7315 (2004).CrossrefGoogle Scholar

  • 18

    C. Bressy, F. Bargiggia, M. Guyonnet, S. Arseniyadis, J. Cossy. Synlett 565 (2009).Google Scholar

  • 19

    S. Kobayashi, T. Tsuchiya, T. Harada, M. Nishide, T. Kurokawa, T. Nakagawa, N. Shimada, K. Kobayashi. J. Antibiot.47, 697 (1994).CrossrefGoogle Scholar

  • 20

    T. Yoshida, K. Koizumi, Y. Kawamura, K. Matsumoto, H. Itazaki. Japan Patent Kokai 5-310726 (1993).Google Scholar

  • 21

    , T. Usui, H. Watanabe, H. Nakayama, Y. Tada, N. Kanoh, M. Kondoh, T. Asao, K. Takio, H. Watanabe, K. Nishikawa, T. Kitahara. Chem. Biol.11, 799 (2004).CrossrefGoogle Scholar

  • 22a

    K. Kawada, K. Yasui, Y. Tamura, T. Nakatani, M. Ohtani. J. Org. Chem.60, 7567 (1995).Google Scholar

  • 22b

    , M. K. Gurjar, J. T. Henri Jr., D. S. Bose, A. V. R. Rau. Tetrahedron Lett.37, 6615 (1996).CrossrefGoogle Scholar

  • 22c

    , M. K. Gurjar, A. Chakrabarti, A. V. R. Rao. Heterocycles45, 7 (1997).CrossrefGoogle Scholar

  • 22d

    , N. Chida, M. Yoshinaga, T. Tobe, S. Ogawa. Chem. Commun. 1043 (1997).CrossrefGoogle Scholar

  • 22e

    , H. Watanabe, H. Watanabe, T. Kitahara. Tetrahedron Lett.39, 8313 (1998).CrossrefGoogle Scholar

  • 22f

    T. Kitahara, H. Watanabe. J. Synth. Org. Chem. Jpn.56, 884 (1998).Google Scholar

  • 22g

    , H. Watanabe, H. Watanabe, M. Bando, M. Kido, T. Kitahara. Tetrahedron55, 9755 (1999).CrossrefGoogle Scholar

  • 22h

    H. Watanabe, H. Watanabe, T. Usui, M. Kondoh, H. Osada, T. Kitahara. J. Antibiot.53, 540 (2000).Google Scholar

  • 22i

    , G. E. Keck, C. E. Knutson, S. A. Wiles. Org. Lett.3, 707 (2001).CrossrefGoogle Scholar

  • 22j

    , L. C. Dias, L. G. de Oliveira, M. A. de Sousa. Org. Lett.5, 265 (2003).CrossrefGoogle Scholar

  • 22k

    C. Dias, L. G. de Oliveira, M. A. de Sousa, R. M. Ellensohn. Arkivoc iv, 62 (2005).Google Scholar

  • 22l

    , K. Shen, A. S. Wasmuth, J. Zhao, C. Zhu, S. G. Nelson. J. Am. Chem. Soc.128, 7438 (2006).CrossrefGoogle Scholar

  • 22l

    D. Enders, S. Dhulut, D. Steinbusch, A. Herrbach. Chem.—Eur. J.13, 3942 (2007).CrossrefGoogle Scholar

  • 23

    , A. Hafner, R. O. Duthaler, R. Marti, G. Ribs, P. Rothe-Streit, F. Schwarzenbach. J. Am. Chem. Soc.114, 2321 (1992).CrossrefGoogle Scholar

  • 24

    R. P. Sonawane, S. R. Joolakanti, S. Arseniyadis, J. Cossy. Synlett 213 (2009).Google Scholar

  • 25

    , C. Bressy, J. P. Vors, S. Hillebrand, S. Arseniyadis, J. Cossy. Angew. Chem., Int. Ed.47, 10137 (2008).CrossrefGoogle Scholar

About the article

Published Online: 2010-05-14

Published in Print: 2010-05-14


Citation Information: Pure and Applied Chemistry, Volume 82, Issue 7, Pages 1365–1373, ISSN (Online) 1365-3075, ISSN (Print) 0033-4545, DOI: https://doi.org/10.1351/PAC-CON-09-09-12.

Export Citation

© 2013 Walter de Gruyter GmbH, Berlin/Boston.Get Permission

Citing Articles

Here you can find all Crossref-listed publications in which this article is cited. If you would like to receive automatic email messages as soon as this article is cited in other publications, simply activate the “Citation Alert” on the top of this page.

[2]
Navjeet Kaur
Synthetic Communications, 2018, Volume 48, Number 13, Page 1551
[3]
Rupinder Kaur, Jitender Bariwal, Leonid G. Voskressensky, and Erik V. Van der Eycken
Chemistry of Heterocyclic Compounds, 2018
[4]
Navjeet Kaur
Inorganic and Nano-Metal Chemistry, 2017, Volume 47, Number 2, Page 163
[5]
Elodie Brun, Véronique Bellosta, and Janine Cossy
The Journal of Organic Chemistry, 2015, Volume 80, Number 17, Page 8668
[6]
Faouzi Chahdoura, Sonia Mallet-Ladeira, and Montserrat Gómez
Org. Chem. Front., 2015, Volume 2, Number 4, Page 312
[7]
Giorgio Abbiati, Fabio Marinelli, Elisabetta Rossi, and Antonio Arcadi
Israel Journal of Chemistry, 2013, Volume 53, Number 11-12, Page 856
[8]
Antonio Arcadi, Federico Blesi, Sandro Cacchi, Giancarlo Fabrizi, Antonella Goggiamani, and Fabio Marinelli
Organic & Biomolecular Chemistry, 2012, Volume 10, Number 48, Page 9700
[9]
A. Stephen K. Hashmi, Mohammad Ghanbari, Matthias Rudolph, and Frank Rominger
Chemistry - A European Journal, 2012, Volume 18, Number 26, Page 8113
[10]
Jesús Manuel Fernández-García, Manuel Á. Fernández-Rodríguez, and Enrique Aguilar
Organic Letters, 2011, Volume 13, Number 19, Page 5172
[11]
Nicolas Gouault, Myriam Le Roch, Adèle Cheignon, Philippe Uriac, and Michèle David
Organic Letters, 2011, Volume 13, Number 16, Page 4371
[12]
N. Meyer, E. Schuh, and F. Mohr
Annual Reports Section "A" (Inorganic Chemistry), 2011, Volume 107, Page 233
[13]
Matthias Rudolph and A. Stephen K. Hashmi
Chemical Communications, 2011, Volume 47, Number 23, Page 6536
[14]
Kalyan Dhara, Sushovan Paladhi, Ganesh Chandra Midya, and Jyotirmayee Dash
Organic & Biomolecular Chemistry, 2011, Volume 9, Number 10, Page 3801

Comments (0)

Please log in or register to comment.
Log in