SYNTHESIS AND METHYLATION PRODUCTS OF 4(5)-(2-FURYL)IMIDAZOLE

Authors

  • Е. В. Власова South-Russian State Technical University
  • В. М. Стоянов South-Russian State Technical University
  • М. М. Ельчанинов South-Russian State Technical University
  • Б. С. Лукьянов Institute of Physical and Organic Chemistry, Southern Federal University

DOI:

https://doi.org/10.1007/3037

Keywords:

2-acetylfuran, copper diacetate, methyl iodide, furacyl bromide, 4(5)-(2-furyl)imidazole, methylation

Abstract

Bromination of 2-acetylfuran with copper(II) bromide in a mixture of ethyl acetate and chloroform leads selectively to furacyl bromide, the nucleophilic substitution of bromine in which by OAc and subsequent use of the Weidenhagen reaction enabled the synthesis of 4(5)‑(2‑furyl)imidazole. On N‑methylation of this imidazole in KOH–acetone 2 isomers are formed, the 1-methyl-4- and 1-methyl-5‑(2-furyl)imidazoles. It was established that, unlike alkylation of 4(5)-phenylimidazole, the main product of the reaction is 1-methyl-5-(2-furyl)imidazole.

How to Cite
Vlasova, E. V.; Stoyanov, V. M.; El'chaninov, M. M.; Lukyanov, B. S. Chem. Heterocycl. Compd. 2010, 46, 681. [Khim. Geterotsikl. Soedin. 2010, 849.]

For this article in the English edition see DOI 10.1007/s10593-010-0569-z

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Published

2016-02-09

Issue

No. 6 (2010)

Section

Original Papers