Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 43, 2013 - Issue 17
474
Views
19
CrossRef citations to date
0
Altmetric
Original Articles

Efficient Synthesis of Symmetrical Bisamides from Aldehydes and Amides Catalyzed by Silica-Bonded S-Sulfonic Acid Nanoparticles

, , &
Pages 2370-2379 | Received 17 Apr 2012, Published online: 03 Jun 2013

REFERENCES

  • Yamazaki , T. ; Numani , K. Y. ; Goodman , M. Cyclic retro-inverso dipeptides with two aromatic side chains, II: Conformational analysis . Biopolymers 1991 , 31 , 1513 – 1528 .
  • Pallai , P. V. ; Struthers , R. S. ; Goodman , M. ; Moroder , L. ; Wunsch , E. ; Vale , W. Partial retro-inverso analogs of somatostatin: Pairwise modifications at residues 7 and 8 and at residues 8 and 9. Biochemistry 1985, 24, 1933–1941.
  • Nunami , K. I. ; Yamazaki , T. ; Goodman , M. Cyclic retro-inverso dipeptides with two aromatic side chains, I: Synthesis . Biopolymers 1991 , 31 , 1503 – 1512 .
  • Rodriguez , M. ; Dubreuil , P. ; Bali , J. P. ; Martinez , J. Synthesis and biological activity of partially modified retro-inverso pseudopeptide derivatives of the c-terminal tetrapeptide of gastrin . J. Med. Chem. 1987 , 30 , 758 – 763 .
  • Fernandez , A. H. ; Alvarez , R. M. ; Abajo , T. M. Improved synthesis of symmetrical N,N′-alkylidene bisamides . Synthesis 1996 , 1299 – 1301 .
  • Magat , E. E. ; Faris , B. F. ; Reith , J. E. ; Salisbury , L. F. Acid-catalyzed reactions of nitriles, II: polyamides from formaldehyde and dinitriles . J. Am. Chem. Soc. 1951 , 73 , 1028 – 1031 .
  • Brace , N. O. ; Mantell , G. J. Hydrophobic compounds and polymers from long-chain alkanamide–formaldehyde condensation reactions . J. Org. Chem. 1961 , 26 , 5176 – 5180 .
  • Noyes , W. A. ; Forman , D. B. Aldehyde—amide condensation, I: reactions between aldehydes and acetamide . J. Am. Chem. Soc. 1933 , 55 , 3493 – 3494 .
  • Zhu , S. ; Xu , G. ; Chu , Q. ; Xu , Y. ; Qui , C. Synthesis of fluorine-containing symmetrical N,N′-alkylidene bisamides . J. Fluorine Chem. 1999 , 93 , 69 – 71 .
  • Selvam , N. P. ; Saranya , S. ; Perumal , P. T. A convenient and efficient protocol for the synthesis of symmetrical N,N′-alkylidine bisamides by sulfamic acid under solvent-free conditions . Can. J. Chem. 2008 , 85 , 32 – 38 .
  • Anary-Abbasinejad , M. ; Mosslemin , M. H. ; Hassanabadi , A. Synthesis of symmetrical bisamides by reaction between aromatic aldehydes and alkyl nitriles in the presence of chlorosulfonic acid . J. Chem. Res. 2009 , 4 , 218 – 219 .
  • (a) Harichandran , G. ; Amalraj , S. D. ; Shanmugam , P. An efficient synthesis of symmetrical N,N′-alkyl-idene bisamides catalyzed by phosphortungstic acid . Indian J. Chem. Sect B. 2011 , 50B , 77 – 82 ; (b) Harichandran , G. ; Amalraj , S. D. ; Shanmugam , P. Boric acid–catalyzed efficient synthesis of symmetrical N,N′-alkylidene bisamides . J. Iran. Chem. Soc. 2011 , 8 , 298 – 305 .
  • Sherrington , D. C. Polymer-supported in synthesis . In Chemistry of Waste Minimization ; J. H. Clark (Ed.); Blackie Academic : London , 1995 .
  • (a) Lu , Z. L. ; Lindner , E. ; Mayer , H. A. Applications of sol gel–processed interphase catalysts . Chem. Rev. 2002 , 102 , 3543 – 3578 ; (b) Wight , A. P. ; Davis , M. E. Design and preparation of organic−inorganic hybrid catalysts . Chem. Rev. 2002 , 102 , 3589 – 3614 .
  • Niknam , K. ; Saberi , D. ; Sadegheyan , M. ; Deris , A. Silica-bonded S-sulfonic acid: An efficient and recyclable solid acid catalyst for the synthesis of 4,4′-(arylmethylene) bis(1H-pyrazol-5-ols) . Tetrahedron Lett. 2010 , 51 , 692 – 694 .
  • Anary-Abbasinejad , M. ; Mosslemin , M. H. ; Hassanabadi , A. ; Tajik , S. p-Toluene sulfonic acid–catalyzed, solvent-free synthesis of symmetrical bisamides by reaction between aldehydes and amides . Synth. Commun. 2010 , 40 , 2209 – 2214 .
  • Mohammad Shafiee , M. R. One-pot preparation of N,N′-alkylidene bisamide derivatives catalyzed by silica-supported polyphosphoric acid (SiO2-PPA) . In International Conference on Biology, Environment and Chemistry (IPCBEE) , Singapore 2011 , 24 , 207 – 211 .
  • (a) Harings , J. A. W. ; Asselen , O. ; Graf , R. ; Broos , R. ; Rastogi , S. The role of superheated water on the crystallization of N,N′-1,2-ethanediyl-bis(6-hydroxy-hexanamide): Implications on crystallography and phase transitions . Crystal Growth Design 2008 , 8 , 2469 – 2477 ; (b) Zweep , N. ; Hopkinson , A. ; Meetsma , A. ; Browne , W. R. ; Feringa , B. L. ; Esch , J. H. Balancing hydrogen bonding and van der Waals interactions in cyclohexane-based bisamide and bisurea organogelators . Langmuir 2009 , 25 , 8802 – 8809 .
  • Javanbakht , M. ; Ganjali , M. R. ; Norouzi , P. ; Badiei , A. ; Hasheminasab , A. ; Abdouss , M. Carbon paste electrode modified with functionalized nanoporous silica gel as a new sensor for determination of silver ion. Electroanalysis 2007, 19, 1307–1314.
  • (a) Yuan , X. ; Lee , H. I. ; Kim , J. W. ; Yie , J. E. ; Kim , J. M. Periodic mesoporous organosilicas functionalized with sulfonic acid group: Synthesis and alkylation of phenol . Chem. Lett. 2003 , 32 , 650 – 651 ; (b) Lee , B. ; Kim , Y. ; Lee , H. ; Yi , J. Synthesis of functhionalized porous silicas via templating method as heavy metal ion adsorbent: The introduction of surface hydrophilicity onto the surface of adsorbents . Microporous Mesoporous Mater. 2001 , 50 , 77 – 90 .

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.