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Synthesis and properties of 2-(2-furyl)[1,3]oxazolo[4,5-b]pyridine

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Abstract

The condensation of 2-amino-3-hydroxypyridine with 2-furoyl chloride according to Ladenburg gave 2-(2-furyl)[1,3]oxazolo[4,5-b]pyridine which was subjected to electrophilic substitution reactions with nitric acid, bromine, hexamethylenetetramine, acetic anhydride, and benzoic acid. In all cases, the electrophile entered exclusively the 5-position in the furan ring. Treatment of the title compound with methyl iodide afforded the corresponding quaternization product at the N4 atom, whereas no Chichibabin amination was observed.

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Authors and Affiliations

  1. Platov South-Russian State Polytechnic University, ul. Prosveshcheniya 132, Novocherkassk, 346428, Russia

    M. M. El’chaninov, A. A. Aleksandrov & E. V. Illenzeer

Authors
  1. M. M. El’chaninov
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  2. A. A. Aleksandrov
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  3. E. V. Illenzeer
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Correspondence to M. M. El’chaninov.

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Original Russian Text © M.M. El’chaninov, A.A. Aleksandrov, E.V. Illenzeer, 2014, published in Zhurnal Organicheskoi Khimii, 2014, Vol. 50, No. 12, pp. 1844–1846.

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El’chaninov, M.M., Aleksandrov, A.A. & Illenzeer, E.V. Synthesis and properties of 2-(2-furyl)[1,3]oxazolo[4,5-b]pyridine. Russ J Org Chem 50, 1826–1828 (2014). https://doi.org/10.1134/S1070428014120197

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  • DOI: https://doi.org/10.1134/S1070428014120197

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