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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 45, 2015 - Issue 22
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Original Articles

Direct Preparation of Amides from Amine Hydrochloride Salts and Orthoesters: A Synthetic and Mechanistic Perspective

Martin J. Di GrandiDepartment of Natural Sciences, Fordham University, New York, New York, USA
,
Caitlin BennettDepartment of Chemistry, Fordham University, Bronx, New York, USA
,
Kristen CaginoDepartment of Chemistry, Fordham University, Bronx, New York, USA
,
Arnold MucciniDepartment of Chemistry, Fordham University, Bronx, New York, USA
,
Corey SuraciDepartment of Chemistry, Fordham University, Bronx, New York, USA
&
Shahrokh SabaDepartment of Chemistry, Fordham University, Bronx, New York, USACorrespondence[email protected]
Pages 2601-2607 | Received 12 Aug 2015, Published online: 18 Nov 2015

REFERENCES

  • For reviews of lysine acetylation of histones, see (a) Turner, B. M. BioEssays 2000, 22, 836–845; (b) Choudhary, C.; Kumar, C.; Gnad, F.; Nielsen, M. L.; Rehman, M.; Walther, T. C.; Olsen, J. V.; Mann, M. Science 2009, 325, 834–840; for reviews of α-tubulin acetylation, see (c) Al-Bassam, J.; Corbett, K. D. Proc. Nat. Acad. Sci. USA 2012, 109, 19515–19516; (d) Rymut, S. M.; Kelley, T. J. Cell Health Cytoskel. 2015, 7, 71–82; for the importance of N-terminal protein acetamides, see (e) Arnesen, T. PLoS Biology 2011, 9, e1001074. doi:10.1371/journal.pbio.1001074.
  • For extensive coverage of the multitude of ways to prepare amides, please see Wuts, G. M. P.; Greene, T. W. In Greene’s Protective Groups in Organic Synthesis, 4th ed.; John Wiley & Sons: New York, 2007; pp. 773–802, and references cited therein.
  • (a) Pelagalli, R.; Chiarotto, I.; Feroci, M.; Vecchio, S. Green Chem. 2012, 14, 2251–2255; (b) Mali, S. M.; Bhaisare, R. D.; Gopi, H. N. J. Org. Chem. 2013, 78, 5550–5555; (c) Alalla, A.; Merabet-Khelassi, M.; Aribi-Zouioueche, L.; Riant, O. Syn. Comm. 2014, 44, 2364–2376.
  • This method provides a highly efficient one-pot procedure for the preparation of a wide range of cyclic amidinium tetrafluoroborate (BF4–) and hexafluorophosphate (PF6–) salts (Scheme 1) by treating primary or secondary diamines with an equimolar quantity each of an orthoester and NH4BF4 or NH4PF6; see Saba, S.; Brescia, A.; Kaloustian, M. Tetrahedron Lett. 1991, 32, 5031–5034.
  • Benhamou, L.; Chardon, E.; Lavigne, G.; Bellemin-Laponnaz, S.; César, V. Chem. Rev. 2011, 111, 2705–2733.
  • Saba, S.; Kojtari, A.; Rivera, M.; D’Amico, P.; Canuso, D.; Kaloustian, M. Abstracts of Papers; 37th Middle Atlantic Regional Meeting of the American Chemical Society: New Brunswick, NJ, 2005.
  • (a) Saba, S.; Vrkic, D.; Cascella, C.; DaSilva, I., Carta, K.; Kojtari, A. J. Chem. Res. 2008, 301–304; (b) O’Connor, D.; Lauria, A.; Bondi, S. P.; Saba, S. Tetrahedron Lett. 2011, 52, 129–132.
  • Saba, S.; Hernandez, R.; Chin Choy, C.; Carta, K.; Bennett, Y.; Bondi, S.; Kolaj, S.; Bennett, C. J. Fluorine Chem. 2013, 153, 168–171.
  • Stewart, W. E.; Siddall III, T. H. Chem. Rev. 1970, 70, 517–551.
  • Gutowsky, H. S.; Holm, C. H. J. Chem. Phys. 1956, 25, 1228–1234.
  • Gibson, S.; Romero, D.; Jacobs, H. K.; Gopalan, A. S. Tetrahedron Lett. 2010, 51, 6737–6740. For a related reaction, please see Rogozhin, S. V.; Davidovich, Y. A.; Korshak, V. V. Izv. Akad. Nauk. SSSR, Ser. Khim. 1970, 3, 727.
  • Taylor, E. C.; Ehrhart, W. A. A. J. Org. Chem. 1963, 28, 1108–1112.
  • Swaringen Jr., R. A.; Eaddy, J. F.; Henderson, T. R. J. Org. Chem. 1980, 45, 3986–3989.
  • McElvain, S. M.; Tate, B. E. J. Am. Chem. Soc. 1945, 67, 202–204.

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