Synlett 2014; 25(16): 2365-2369
DOI: 10.1055/s-0034-1378580
letter
© Georg Thieme Verlag Stuttgart · New York

Synthesis of α-Functionalized Amides by a Ritter Reaction in the Presence of NaHSO4/SiO2

Mamiko Hayakawa
a  Department of Materials and Applied Chemistry, College of Science and Technology, Nihon University, Kanda Surugadai, Chiyoda-ku, ­Tokyo 101-8308, Japan   URL: aoyama.tadashi@nihon-u.ac.jp
,
Tadashi Aoyama*
a  Department of Materials and Applied Chemistry, College of Science and Technology, Nihon University, Kanda Surugadai, Chiyoda-ku, ­Tokyo 101-8308, Japan   URL: aoyama.tadashi@nihon-u.ac.jp
,
Toshiya Kobayashi
a  Department of Materials and Applied Chemistry, College of Science and Technology, Nihon University, Kanda Surugadai, Chiyoda-ku, ­Tokyo 101-8308, Japan   URL: aoyama.tadashi@nihon-u.ac.jp
,
Toshio Takido
a  Department of Materials and Applied Chemistry, College of Science and Technology, Nihon University, Kanda Surugadai, Chiyoda-ku, ­Tokyo 101-8308, Japan   URL: aoyama.tadashi@nihon-u.ac.jp
,
Mitsuo Kodomari
b  The Institute of Natural Science, College of humanities and Science, Nihon University, Sakurajosui, Setagaya-ku, Tokyo 156-8550, Japan
› Author Affiliations
Further Information

Publication History

Received: 12 June 2014

Accepted after revision: 11 July 2014

Publication Date:
13 August 2014 (online)


Abstract

A simple and efficient method has been developed for the synthesis of α-functionalized amide from alcohols and nitriles in the presence of silica gel supported sodium hydrogen sulfate ­(NaHSO4/SiO2). For example, benzhydrol was allowed to react with bromoacetonitrile in the presence of NaHSO4/SiO2 in 1,2-dichloroethane to yield N-(diphenylmethyl)-2-bromoacetamide.

Supporting Information

 
  • References

    • 1a Sheehan JC, Lengyel I. J. Am. Chem. Soc. 1964; 86: 1356
    • 1b Murphy NS, Prabhakaran P, Azzarito V, Plante JP, Hardie MJ, Kilner CA, Warriner SL, Wilson AJ. Chem. Eur. J. 2013; 19: 5546
    • 1c Zubarev AA, Shestopalov AM, Larionova NA, Rodinovskaya LA, Shestopalov AA. Tetrahedron 2013; 69: 9648
    • 2a Clark-Lewis JW. Chem. Rev. 1958; 58: 63
    • 2b Rossi L, Feroci M, Verdecchia M, Inesi A. Lett. Org. Chem. 2005; 2: 731
  • 3 Touti F, Maurin P, Hasserodt J. Eur. J. Org. Chem. 2009; 1495
  • 4 Baumgarten HE, Chiang NR, Eria VJ, Beum PV. J. Org. Chem. 1985; 50: 5507
  • 5 Forti L, Ghelfi F, Munari F, Pagnoni UM. Tetrahedron 1995; 51: 12285
  • 6 Lucas RL, Zart MK, Murkerjee J, Sorrell TN, Powell DR, Borovik AS. J. Am. Chem. Soc. 2006; 128: 15476
  • 7 Aoyama T, Miyota S, Takido T, Kodomari M. Synlett 2011; 2971
  • 8 Yadav JS, Subba Reddy BV, Pandurangam T, Jayasudan Reddy Y, Gupta MK. Catal. Commun. 2008; 9: 1297
  • 9 Khalafi-Nezhad A, Foroughi HO, Doroodmand MM, Panahi F. J. Mater. Chem. 2011; 21: 12842
    • 10a Sato Y, Aoyama T, Takido T, Kodomari M. Tetrahedron 2012; 68: 7077
    • 10b Aoyama T, Koda S, Takeyoshi Y, Ito T, Takido T, Kodomari M. Chem. Commun. 2013; 49: 6605
    • 10c Aoyama T, Yamamoto T, Miyota S, Hayakawa M, Takido T, Kodomari M. Synlett 2014; 25: 1571
  • 11 Gullickson GC, Lewis DE. Aust. J. Chem. 2003; 56: 385