Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 40, 2009 - Issue 2
3,421
Views
24
CrossRef citations to date
0
Altmetric
Original Articles

Additive-Free Chemoselective Acylation of Amines

, , &
Pages 295-302 | Received 22 Dec 2008, Published online: 29 Dec 2009

REFERENCES

  • Paul , S. ; Nanda , P. ; Gupta , R. ; Loupy , A. Ac2O-Py/basic alumina as a versatile reagent for acetylations in solvent-free conditions under microwave irradiation . Tetrahedron Lett. 2002 , 43 , 4261 , and literature cited therein .
  • (a) Kadam , S. T. ; Kim , S. S. Phosphomolybdic acid: Mild and efficient catalyst for acetylation of alcohols, phenols, and amines under solvent-free conditions . Synthesis 2008 , 267 , and literature cited therein; (b) Li , A.-X. ; Li , T.-S. ; Ding , T.-H. Montmorillonite K-10 and KSF as remarkable acetylation catalysts . Chem. Commun. 1997 , 1389 .
  • (a) Sarvari , M. H. ; Sharghi , H. Zinc oxide (ZnO) as a new, highly efficient, and reusable catalyst for acylation of alcohols, phenols, and amines under solvent-free conditions . Tetrahedron 2005 , 61 , 10903 ; (b) Chen , C.-T. ; Kuo , J.-H. ; Pawar , V. D. ; Munot , Y. S. ; Weng , S.-S. ; Ku , C.-S. ; Liu , C.-Y. Nucleophylic acyl substitutions of anhydrides with protic nucleophiles catalyzed by amphoteric, oxomolybdenum species . J. Org. Chem. 2005 , 70 , 1188 .
  • (a) Herbst , R. M. ; Shemin , D. Acetylglycine . Org. Synth., Coll. Vol. II ; John Wiley & Sons : London , 1943 , p. 11 ; (b) Parkes, G. D.; Farthing, A. C. Derivatives of 2,4,6-trinitrotoluene: Monoreduction of polynitro-compounds. J. Chem. Soc. 1948, 1275; (c) Richardson, A. C.; McLauchlan, K. A. 3-Amino-3,6-dideoxy-derivatives of L-glucose, L-galactose, and L-talose. J. Chem. Soc. 1962, 2499; (d) Watanabe, K. A.; Fox, J. J. A simple method for selective acylation of cytidine on the 4-amino group. Angew. Chem., Int. Ed. Engl. 1966, 5, 579; (e) Chua, M.-S.; Shi, D.-F.; Wrigley, S.; Bradshaw, T. D.; Hutchinson, I.; Shaw, P. N.; Barrett, D. A.; Stanley, L. A.; Stevens, M. F. G. Antitumor benzothiazole, 7: Synthesis of 2-(4-acylaminophenyl)benzothiazoles and investigations into the role of acetylation in the antitumor activities of parent amines. J. Med. Chem. 1999, 42, 381; (f) Awasthi, A. K.; Paul, K. A new and improved synthesis of bidisomide. Org. Proc. Res. Dev. 2001, 5, 528; (g) Bertrand, M. B.; Wolfe, J. P. Stereoselective synthesis of N-protected pyrrolidines via Pd-catalyzed reactions of γ-(N-acylamino) alkanes and γ-(N-Boc-amino) alkenes with aryl bromide. Tetrahedron 2005, 61, 6447; (h) Forrest, E. M.; Cochran, B. M. Room temperature palladium-catalyzed intramolecular hydroamination of unactivated alkenes. J. Am. Chem. Soc. 2006, 128, 4246 .
  • (a) Easton , N. R. ; Dillard , R. D. Acetylenic amines, VI: Amides of secondary acetylenic amines . J. Org. Chem. 1963 , 28 , 2465 ; (b) Heyde , C. ; Zug , I. ; Hartmann , H. A simple route to N,N-dialkyl derivatives of 2-amino-5-thiophenecarboxilates . Eur. J. Org. Chem. 2000 , 3273 ; (c) Auberson , Y. P. ; Allgeir , H. ; Bischoff , S. ; Lingenhoehl , K. ; Moretti , R. ; Schmutz , M. 5-Phosphonomethylquinoxalinediones as competitive NMDA receptor antagonists with preference for the human 1A/2A, rather than 1A/2B receptor composition . Bioorg. Med. Chem. Lett. 2002 , 12 , 1099 ; (d) Guarda , V. L. M. ; Perrissin , M. ; Thomasson , F. ; Ximenes , E. A. ; Galdino , S. L. ; Pitta , I. R. ; Luu-Duc , C. ; Barbe , J. Synthesis of 4-octyl-2H-1,4-benzo-thiazin-3-ones . Eur. J. Med. Chem. 2003 , 38 , 769 ; (e) Adler , T. ; Bonjoch , J. ; Clayden , J. ; Font-Bardia , M. ; Pickworth , M. ; Solans , X. ; Solé , D. ; Vallverdù , L. Slow interconversion of enantiomeric conformers or atropisomers of anilides and urea derivatives of 2-substituted anilines . Org. Biomol. Chem. 2005 , 3 , 3173 ; (f) Martin , J. E. D. ; Mehlecke , C. M. ; Gamba , M ; Costa , V. e. U. Synthesis of chiral norbornane derivatives as γ-amino alcohol catalysts: The effect of the functional group positions on the chirality transfer . Tetrahedron: Asymmetry 2006 , 17 , 1817 ; (g) Mojtahedi , M. M. ; Abaee , M. S. ; Heravi , M. M. ; Behbahani , F. K. Additive-free chemoselective acylation of amines and thiols . Monatsh. Chem. 2007 , 138 , 95 .
  • (a) Kang , Y.-J. ; Chung , H.-A. ; Kim , J.-J. 2-Acylpyridazin-3-ones: Novel, mild, and chemoselective acylating agents for amines. Synthesis 2002, 733; (b) Ranu , B. C. ; Dutta , P. ; Sarkar , A. Highly selective acylation of alcohols and amines by an indium triiodide–catalysed transesterification process. J. Chem. Soc., Perkin Trans. 1 2000, 2223; (c) Kondo , K. ; Sekimoto , E. ; Nakao , J. ; Murakami , Y. Studies on development of sufficiently chemoselective N-acylation reagents: N-acyl-N-(2,3,4,5,6-Pentafluorophenyl)methanesulfonamides. Tetrahedron 2000, 56, 5843; (d) Morcuende , A. ; Ors , M. ; Valverde , S. ; Herradon , B. Microwave-promoted transformations: Fast and chemoselective N-acylation of amino alcohols using catalytic amounts of dibutyltin oxide: Influence of the power output and the nature of the acylating agent on the selectivity. J. Org. Chem. 1996, 61, 5264; (e) Kisfaludy , L. ; Mohacsi , T. ; Low , M. ; Drexler , F. Pentafluorophenyl acetate: A new, highly selective acetylating agent. J. Org. Chem. 1979, 44, 654.
  • Naik , S. ; Bhattacharjya , G. ; Talukdar , B. ; Patel , B. K. Chemoselective acylation of amines in aqueous media . Eur. J. Org. Chem. 2004 , 1254 .
  • Kikugawa , Y. ; Mitsui , K. ; Sakamoto , T. ; Kawase , M. ; Tamiya , H. N-methoxydiacetamide: A new selective acetylating agent . Tetrahedron Lett. 1990 , 31 , 243 and literature cited therein .
  • Katritzky , A. R. ; Suzuki , K. ; Wang , Z. Acylbenzotriazoles as advanageous N-, C-, S-, and O-acylating agents . Synlett 2005 , 1656 .
  • (a) Pagani , G. ; Baruffini , A. ; Borgna , P. ; Caccialanza , C. Acidi ftalamici variamente N-sostituiti . Farmaco 1968 , 23 , 448 ; (b) Schultz , E. M. ; Bolhofer , W. A. ; Augenblick , A. ; Bicking , J. B. ; Habecker , C. N. ; Horner , J. K. ; Kwong , S. F. ; Pietruszkiewicz , A. M. Maleamic acids that affect plasma cholesterol and penicillin excretion . J. Med. Chem. 1967 , 10 , 717 .
  • Yoshimura , T. ; Koide , Y. ; Shosenji , H. ; Esumi , K. Preparation and surface-active properties of N-alkyl maleamic acid telomere type surfactants having several hydrocarbon chains . J. Oleo Sci. , 2002 , 51 , 229 .

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.