Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 39, 2009 - Issue 6
21,719
Views
41
CrossRef citations to date
0
Altmetric
Original Articles

Highly Efficient Michael Addition Reaction of Amines Catalyzed by Silica-Supported Aluminum Chloride

, &
Pages 1109-1119 | Received 02 Jul 2008, Published online: 25 Feb 2009

REFERENCES

  • Azizi , N. ; Saidi , M. R. Novel and efficient method for the silylation of hydroxyl groups with hexamethyldisilazane (HMDS) under solvent-free and neutral conditions . Organometallics 2004 , 23 , 1457 – 1458 .
  • Azizi , N. ; Saidi , M. R. LiClO4 accelerated Michael addition of amines to α,β-unsaturated olefins under solvent-free conditions . Tetrahedron 2004 , 60 , 383 – 387 .
  • Azizi , N. ; Saidi , M. R. Lithium perchlorate–catalyzed three–component coupling: A facile and general method for the synthesis of α-aminophosphonates under solvent-free condition . Eur. J. Org. Chem. 2003 , 4630 – 4633 .
  • Azizi , N. ; Saidi , M. R. Highly chemoselective addition of amines to epoxides in water . Org. Lett. 2005 , 7 , 3649 – 3651 .
  • Yang , L. ; Xu , L.-W. ; Zhou , W. ; Li , L. ; Xia , C.-G. Highly efficient aza-Michael reactions of aromatic amines and N-heterocycles catalyzed by a basic ionic liquid under solvent-free conditions . Tetrahedron Lett. 2006 , 47 , 7723 – 7726 .
  • Yadav , J. S. ; Ramesh Reddy , A. ; Gopal Rao , Y. ; Narsaiah , A. V. ; Reddy , B. V. S. Lanthanum trichloride (LaCl3): An efficient catalyst for conjugate addition of amines to electron-deficient olefins . Lett. Org. Chem. 2007 , 4 , 462 – 464 .
  • Khan , A. T. ; Parvin , T. ; Gazi , S. ; Choudhury , L. H. Bromodimethyl-sulfonium bromide-mediated Michael addition of amines to electron deficient alkenes . Tetrahedron Lett. 2007 , 48 , 3805 – 3808 .
  • Mukherjee , C. ; Misra , A. K. Aza-Michael addition of amines to activated alkenes catalyzed by silica supported perchloric acid under a solvent-free condition . Lett. Org. Chem. 2007 , 4 , 54 – 59 .
  • Duan , Z. ; Xuan , X. ; Li , T. ; Yang , C. ; Wu , Y. Cerium(IV) ammonium nitrate (CAN) catalyzed aza-Michael addition of amines to α,β-unsaturated electrophiles . Tetrahedron Lett. 2006 , 47 , 5433 – 5436 .
  • Varala , R. ; Sreelatha , N. ; Adapa , S. R. Ceric ammonium nitrate catalyzed aza-Michael addition of aliphatic amines to α,β-unsaturated carbonyl compounds and nitriles in water . Synlett 2006 , 1549 – 1553 .
  • Surendra , K. ; Krishnaveni , N. S. ; Sridhar , R. ; Rao , K. R. β-Cyclodextrin promoted aza-Michael addition of amines to conjugated alkenes in water . Tetrahedron Lett. 2006 , 47 , 2125 – 2127 .
  • Meshram , H. M. ; Lakshindra , C. ; Reddy , P. N. ; Sadashiv , K. ; Yadav , J. S. Zirconium(IV) chloride–mediated chemoselective conjugate addition of aliphatic amines to α,β-ethylenic compounds . Synth. Commu. 2006 , 36 , 795 – 801 .
  • Yadav , J. S. ; Ramesh Reddy , A. ; Gopal Rao , Y. ; Narsaiah , A. V. ; Subba Reddy , B. V. Samarium(III) triflate catalyzed conjugate addition of amines to electron-deficient alkenes . Synthesis 2007 , 3447 – 3450 .
  • Hashemi , M. M. ; Eftekhari-Sis , B. ; Abdollahifar , A. ; Khalili , B. ZrOCl2 · 8H2O on montmorillonite K10 accelerated conjugate addition of amines to α,β-unsaturated alkenes under solvent-free conditions. Tetrahedron 2006, 62, 672–677.
  • Bo , K. L. ; Wu , Q. ; Xue , Q. Q. ; De , S. L. ; Xian , F. L. N-methyl-imidazole as a promising catalyst for the aza-Michael addition reaction of N-heterocycles . Synthesis 2007 , 2653 – 2659 .
  • Das , B. ; Chowdhury , N. Amberlyst-15: An efficient reusable heterogeneous catalyst for aza-Michael reactions under solvent-free conditions . J. Mol. Catal. A: Chem. 2007 , 263 , 212 – 215 .
  • Yeom , C.-E. ; Kim , M. J. ; Kim , B. M. ; Choudhury , L. H. 1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU)-promoted efficient and versatile aza-Michael addition . Tetrahedron 2007 , 63 , 904 – 909 .
  • Monfray , J. ; Koskinen , A. M. P. Aza-Michael additons on α,β-unsaturated esters catalyzed by bismuth(III) triflate in conventional chemistry and under microwave irradiation . Lett. Org. Chem. 2006 , 3 , 324 – 327 .
  • Vijender , M. ; Kishore , P. ; Satyanarayana , B. Cadmium chloride (CdCl2): An efficient catalyst for conjugate addition of amines to electron-poor alkenes . Synth. Commun. 2007 , 37 , 591 – 594 .
  • Bhanushali , M. J. ; Nandurkar , N. S. ; Jagtap , S. R. ; Bhanage , B. M. Y(NO3)3 · 6H2O catalyzed aza-Michael addition of aromatic/hetero-aromatic amines under solvent-free conditions . Catal. Commun. 2008 , 9 , 1189 – 1195 .
  • Reddy , K. R. ; Kumar , N. S. Cellulose-supported copper(0) catalyst for aza-Michael addition . Synlett 2006 , 2246 – 2250 .
  • Borujeni , K. P. ; Tamami , B. Polystyrene and silica gel supported AlCl3 as highly chemoselective heterogeneous Lewis acid catalysts for Friedel–Crafts sulfonylation of aromatic compounds . Catal. Commun. 2007 , 8 , 1191 – 1196 .
  • Borujeni , K. P. Silica-gel-supported aluminum chloride: A stable, efficient, selective, and reusable catalyst for tetrahydropyranylation of alcohols and phenols . Synth. Commun. 2006 , 36 , 2705 – 2710 .
  • Tamami , B. ; Borujeny , K. P. Chemoselective protection of carbonyl compounds as dithioacetals using silica gel supported aluminum chloride . Synth. Commun. 2003 , 33 , 4253 – 4258 .
  • Tamami , B. ; Borujeny , K. P. Chemoselective protection of carbonyl compounds as dithioacetals using polystyrene and silica gel supported AlCl3 and FeCl3 . Iran. Polym. J. 2003 , 12 , 507 – 513 .
  • Li , Z. ; Ma , X. ; Liu , J. ; Feng , X. ; Tian , G. ; Li Zhu , A. Silica-supported aluminum chloride: A recyclable and reusable catalyst for one-pot three-component Mannich-type reactions . J. Mol. Catal. A: Chem. 2007 , 272 , 132 – 135 .
  • Clark , J. H. Solid acids for green chemistry . Acc. Chem. Res. 2002 , 35 , 791 – 797 .
  • Ziyaei-Halimjani , A. ; Saidi , M. R. An efficient one-pot Michael addition of dithiocarbamate anion to α,β-unsaturated olefins . J. Sulfur Chem. 2005 , 26 , 149 – 154 .
  • Rajabi , F. ; Saidi , M. R. Solid lithium perchlorate-mediated conjugate addition of thiols and indoles to α,β-unsaturated carbony compounds. J. Sulfur Chem. 2005, 26, 251–259.
  • Saidi , M. R. ; Rajabi , F. ; Brown , R. S. Enantioselective conjugate addition to α,β-unsaturated esters and amides mediated by lithium perchlorate . J. Iran. Chem. Soc. 2005 , 2 , 300 – 304 .
  • Azizi , N. ; Arynasab , F. ; Saidi , M. R. Efficient Friedel-Crafts alkylation of indoles and pyrrole with enones and nitroalkene in water . Org. & Biomol. Chem. 2006 , 4275 – 4277 .
  • Azizi , N. ; Aryanadab , F. ; Torkian , L. ; Ziyaei-Halimjani , A. ; Saidi , M. R. One-pot synthesis of dithiocarbamates accelerated in water . J. Org. Chem. 2006 , 71 , 3634 – 3635 .
  • Xu , T. ; Kob , N. ; Drago , R. S. ; Nicholas , J. B. ; Haw , J. F. A solid acid catalyst at the threshold of superacid strength: NMR, calorimetry, and density functional theory studies of silica-supported aluminum chloride . J. Am. Chem. Soc. 1977 , 119 , 12231 – 12239 .

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.