Conclusions
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1.
4-Methyl-5-(α-oxo-Β-bromo-ε-ethoxycarbonylpentyl)imidazolinone-2 reacts with diethylamine with migration of the electrophilic reaction center to give 4-diethylaminomethyl-5-(α-oxo-ε-ethoxycarbonylpentyl)imidazolinone-2.
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2.
Sulfur-containing nucleophilic reagents and potassium benzoate enter into a nucleophilic substitution reaction with 4-methyl-5-(α-oxo-Β-bromo-ε-ethoxycarbonylpentyl)imidazolinone-2 without migration of the reaction center.
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3.
Direct conversion of 1,3-diacetyl-4-acetoxymethyl-5-(α-oxo-ε-ethoxycarbonylpentyl)imidazolinone-2 to 4-methoxymethyl-5-(α-oxo-ε-methoxycarbonylpentyl)imidazolinone-2, an intermediate product in the synthesis of the methyl ester of 3,4-dehydrobiotin, is realized by the reaction with a solution of sulfuric acid in methanol.
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Literature cited
S. I. Zav'yalov and L. B. Kulikova, Izv. Akad. Nauk SSSR, Ser. Khim., 957 (1984).
T. Mikaiyama, Y. Sato, T. Taguchi, and K. Watanabe, Japan Kokai, 76138692, Chem. Abstr.,87, 53292 (1977).
S. I. Zav'yalov, N. A. Rodionova, and E. P. Gracheva, Izv. Akad. Nauk SSSR, Ser. Khim., 2025 (1972).
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S. I. Zav'yalov, L. B. Kulikova, and O. V. Dorofeeva, Izv. Akad. Nauk SSSR, Ser. Khim., 2381 (1987).
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 7, pp. 1616–1619, July, 1989.