Formation of 3-pyrrolin-2-one or imidazolidine derivatives by slow dimerization of N-substituted aziridine-2-carboxylates

被引：0

作者：

Yu. V. Tomilov

G. P. Okonnishnikova

E. V. Shulishov

V. A. Korolev

机构：

[1] Russian Academy of Sciences,N. D. Zelinsky Institute of Organic Chemistry

来源：

Russian Chemical Bulletin | 2005年 / 54卷

关键词：

aziridine-2-carboxylates; imidazolidine-2,4-dicarboxylates; 3-amino-3-pyrrolin-2-ones; isomerization; condensation;

D O I：

暂无

中图分类号：

学科分类号：

摘要：

Prolonged storage (45–60 days) of N-methyl- or N-cyclopropylaziridine-2-carboxylates leads to their dimerization through the N—C(3) bond cleavage to form 1,3-disubstituted 2-methylimidazolidine-2,4-dicarboxylates in high yields. Prolonged storage of 1-benzyl-aziridine-2-carboxylate (like the reactions of alkyl pyruvates with primary amines) results in cyclocondensation to yield 3-pyrrolin-2-one derivative.

引用

页码：1052 / 1056

页数：4

共 33 条

[1]

Gladysheva F. N.(1970)undefined Usp. Khim. 39 235-undefined

[2]

Sineokov A. P.(1963)undefined Angew. Chem., Int. Ed. Engl. 2 565-undefined

[3]

Etlis V. S.(1985)undefined J. Org. Chem. 50 2309-undefined

[4]

Huisgen R.(1991)undefined J. Heterocycl. Chem. 28 1757-undefined

[5]

deShong Ph.(1982)undefined Bull. Chem. Soc. Jpn 55 3049-undefined

[6]

Kell D. A.(1996)undefined Tetrahedron 52 9909-undefined

[7]

Sidler D. R.(1988)undefined Izv. Akad. Nauk SSSR. Ser. Khim. 37 1110-undefined

[8]

Bouayad Z.(1953)undefined J. Am. Chem. Soc. 75 5045-undefined

[9]

Chanet-Ray J.(1972)undefined Chem. Ber. 105 312-undefined

[10]

Ducher S.(undefined)undefined undefined undefined undefined-undefined

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