Abstract
When N-methoxycarbonyl and N-benzoxycarbonyl derivatives of methyl esters of aziridine-2-carboxylic acid, L-proline, L-thioproline, and pipecolic acid interact with NaBH4 in tert-butanol/methanol, the products of reduction of the C-methoxycarbonyl group of the original compounds are accompanied by bicyclic urethanes and oxazolidines. Reduction of N-maleates and N-fumarates of heterocyclic α-iminocarboxylic acids leads to the formation of α-hydroxymethyl-N-[4-(2-oxo-2,5-dihydrofuryl)] derivatives of pyrrolidine, piperidine, 1,3-thiazolidine, and 1,4-thiazan. In the latter case, 1-aza-2-hydroxymethyl-4-oxo-5-oxa-9-thiabicyclo [5.4.0]undecene-2 is also obtained. The N-maleates and fumarates of aziridine-2-carboxylic acid are reduced anomalously by sodium borohydride, forming 2-hydroxymethyl-2-(β-hydroxyethyl)-3-oxa-1-azabicyclo[3.1.0]hexanes.
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For Communication 3 see [2].
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1567–1573, November, 1993.
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Nurdinov, R., Liepin'sh, É.É. & Kalvin'sh, I.Y. Derivatives of heterocyclic α-iminocarboxylic acids. 4. Reduction of N-alkoxycarbonyl derivatives of α-iminocarboxylic acids. Chem Heterocycl Compd 29, 1352–1357 (1993). https://doi.org/10.1007/BF00532039
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DOI: https://doi.org/10.1007/BF00532039