Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 40, 2010 - Issue 15
1,650
Views
24
CrossRef citations to date
0
Altmetric
Original Articles

Solid–Liquid Phase Alkylation of N-Heterocycles: Microwave-Assisted Synthesis as an Environmentally Friendly Alternative

, , , &
Pages 2291-2301 | Received 03 Jun 2009, Published online: 07 Jul 2010

REFERENCES

  • Stefanidakis , G. ; Gwyn , J. E. Alkylation ; In Chemical Processing Handbook ; J. J. McKetta (Ed.) ; CRC Press : Boca Raton , FL , 1993 ; pp. 88 – 138 .
  • Dörwald , F. Z. Side Reactions in Organic Synthesis: A Guide to Successful Synthesis Design ; Wiley-VHC : Weinheim , 2005 ; Ch. 6 , pp. 229 – 251 .
  • Price , C. C. The alkylation of aromatic compounds by the Friedel–Crafts method ; In Organic Reactions ; R. Adams (Ed.) ; John Wiley : New York , 1946 ; Vol. 3 , Ch. 1 , pp. 1 – 82 .
  • Keglevich , G. ; Novák , T. ; Vida , L. ; Greiner , I. Microwave irradiation as an alternative to phase transfer catalysis in the liquid-solid phase, solvent-free C-alkylation of active methylene containing substrates . Green Chem. 2006 , 8 , 1073 – 1075 .
  • Keglevich , G. ; Majrik , K. ; Vida , L. ; Greiner , I. Microwave irradiation as a green alternative to phase transfer catalysis: Solid–liquid phase alkylation of active methylene containing substrates under solvent-free conditions . Lett. Org. Chem. 2008 , 5 , 224 – 228 .
  • Keglevich , G. ; Bálint , E. ; Karsai , É. ; Grün , A. ; Bálint , M. ; Greiner , I. Chemoselectivity in the microwave-assisted solvent-free solid–liquid phase benzylation of phenols: O-versus C-alkylation . Tetrahedron Lett. 2008 , 49 , 5039 – 5042 .
  • Keglevich , G. ; Bálint , E. ; Karsai , É. ; Varga , J. ; Grün , A. ; Bálint , M. ; Greiner , I. Heterogeneous phase alkylation of phenols making use of phase transfer catalysis and microwave irradiation . Lett. Org. Chem. 2009 , 6 , 535 – 539 .
  • Keglevich , G. ; Sypaseuth , F. D. ; Grün , A. ; Karsai , É. ; Greiner , I. The role of phase transfer catalyst in the microwave-assisted N-benzylation of amides, imides, and N-heterocycles . Lett. Org. Chem. 2009 , 6 , 529 – 534 .
  • Bogdal , D. ; Pielichowski , J. ; Jaskot , K. Remarkably fast N-alkylation of azaheterocycles under microwave irradiation in dry media . Heterocycles 1997 , 45 , 715 – 722 .
  • Hoechster Farbw. Procedure for the preparation of N-methylcarbazole. DE Patent 255304 , 1912 .
  • Kricka , L. J. ; Ledwith , A. Reactions of condensed N-heteroaromatic molecules, part I: Alkylation by thallium(I) ethoxide . J. Chem. Soc., Perkin Trans. 1 1972 , 2292 – 2293 .
  • Buu-Hoї , N. G. P. H. ; Royer , R. Potential nitrogen-heterocycle carcinogens, XI: Substitution reaction of N-alkylcarbazoles . J. Org. Chem. 1951 , 16 , 1198 – 1205 .
  • Pellicciari , R. ; Curini , M. ; Spagnoli , N. ; Ceccherelli , P. Reaction of alkoxycarbonylcarbenoids with imidazole: An improved preparation of ethyl imidazole-1-ylacetate and the first synthesis of diethyl imidazole-1-ylmalonat . Synthesis 1981 , 8 , 629 – 631 .
  • Begg , C. G. ; Grimmett , M. R. ; Wethey , P. D. The thermally induced rearrangement of 1-substituted imidazoles . Aust. J. Chem. 1973 , 26 , 2435 – 2446 .
  • Cacace , F. ; Giuliano , R. ; Inam-ul-Haq . The N-acetyl-benzimidazole acid and its auxinic activity . Atti Accad. Naz. Lincei, Rend. Classe Sci. Fis. Mat. Nat. 1957 , 22 , 510 – 513 .
  • Forrester , J. ; Ray , V. H. ; Newton , L. ; Preston , P. N. Synthesis and reactivity of benzylic sulfonium salts: Benzylation of phenol and thiophenol under near-neutral conditions . Tetrahedron 2001 , 57 , 2871 – 2884 .
  • Fawaz , A. ; Russel , B. W. Radical cyclisation onto imidazoles and benzimidazoles . Tetrahedron 1999 , 55 , 4109 – 4122 .
  • Zhigachev , V. E. ; Suvorov , N. N. Darzens condensation of indoles. Tr. Mosk. Khim.-Tekhnol. Inst. 1969, 61, 150–153.
  • Kurihara , T. ; Fujimoto , T. ; Harusawa , S. ; Yoneda , R. Simple N-alkylation and N-acylation of 3-acetylindole and 3-indolecarbaldehyde . Synthesis 1987 , 4 , 396 – 397 .
  • Bouerat , L. M. E. ; Fensholdt , J. ; Nielsen , S. F. ; Liang , X. ; Havez , S. E. ; Andersson , E. C. ; Jensen , L. ; Hansen , J. R. Novel therapeutic use of indolinone derivatives. WO Patent 2005/058309 A1, 2005 .

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.