Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 37, 2007 - Issue 15
669
Views
14
CrossRef citations to date
0
Altmetric
Original Articles

Synthesis of the Substituted 3‐Cyclobutene‐1,2‐diones

, , &
Pages 2527-2542 | Received 04 Aug 2006, Published online: 09 Aug 2007

References

  • Lee , C. W. , Cao , H. , Ichiyama , K. and Rana , T. M. 2005 . Design and synthesis of a novel peptidomimetic inhibitor of HIV‐1 Tat‐TAR interactions: Squaryldiamide as a new potential bioisostere of unsubstituted guanidine . Bioorg. Med. Chem. Lett. , 15 : 4243 – 4246 .
  • Porter , J. R. , Archibald , S. C. , Childs , K. , Critchley , D. , Head , J. S. , Linsley , J. M. , Parton , T. A. , Robinson , M. K. , Shock , A. , Taylor , R. J. , Warrellow , G. J. , Alexander , R. P. and Langham , B. 2002 . Squaric acid derivatives as VLA‐4 integrin antagonists . Bioorg. Med. Chem. Lett. , 12 : 1051 – 1054 .
  • Cavanagh , R. L. 1985 . BMY‐25368 . Drugs Fut. , 10 : 890
  • Prous , J. and Castañer , J. 1990 . IT‐066 . Drugs Fut. , 15 : 1181
  • Gilbert , A. M. , Antane , M. M. , Argentieri , T. M. , Butera , J. A. , Francisco , G. D. , Freeden , C. , Gundersen , E. G. , Graceffa , R. F. , Herbst , D. , Hirth , B. H. , Lennox , J. R. , McFarlane , G. , Norton , N. W. , Quagliato , D. , Sheldon , J. H. , Warga , D. , Wojdan , A. and Woods , M. 2000 . Design and SAR of novel potassium channel openers targeted for urge urinary incontinence, 2: Selective and potent benzylamino cyclobutenediones . J. Med. Chem. , 43 : 1203 – 1214 .
  • Kinney , W. A. , Abou‐Gharbia , M. , Garrison , D. T. , Schmid , J. , Kowal , D. M. , Bramlett , D. R. , Miller , T. L. , Tasse , R. P. , Zaleska , M. M. and Moyer , J. A. 1998 . Design and synthesis of [2‐(8,9‐dioxo‐2,6‐diazabicyclo[5.2.0]non‐1(7)‐en‐2‐yl)‐ethyl]phosphonic acid (EAA‐090), a potent N‐methyl‐D‐aspartate antagonist, via the use of 3‐cyclobutene‐1,2‐dione as an achiral alpha‐amino acid bioisostere . J. Med. Chem. , 41 : 236 – 246 .
  • Onaran , M. B. , Comeau , A. B. and Seto , C. T. 2005 . Squaric acid‐based peptidic inhibitors of matrix metalloprotease—1 . J. Org. Chem. , 70 : 10792 – 10802 .
  • Yagi , S. , Fujie , Y. , Hyodo , Y. and Nakazumi , H. 2002 . Synthesis, structure, and complexation properties with transition metal cations of a novel methine‐bridged bisquarylium dye . Dyes Pigm. , 52 : 245 – 252 .
  • Lim , N. C. , Morton , M. D. , Jenkins , H. A. and Brückner , C. 2003 . Squaric acid N‐hydroxylamides: Synthesis, structure, and properties of vinylogous hydroxamic acid analogues . J. Org. Chem. , 68 : 9233 – 9241 .
  • Xie , J. , Comeau , A. B. and Seto , C. T. 2004 . Squaric acids: A new motif for designing inhibitors of protein tyrosine phosphatases . Org. Lett. , 6 : 83 – 86 .
  • Liu , H. , Tomooka , C. S. and Moore , H. W. 1997 . An efficient general synthesis of squarate esters . Synth. Commun. , 27 : 2177 – 2180 .
  • Masatomi , O. , Yoshihiko , Y. , Yuhichi , S. and Shoji , E. 1993 . Synthesis of squaric acid derivatives by Lewis acid‐catalysed reaction of its dichloride, methyl ester chloride, diethylamide chloride, and ethyl diester with unsaturated organosilanes: New method for C‐C bond formation on cyclobutenedione . J. Chem. Soc., Perkin Trans. 1 , 2 : 263 – 271 .

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.