Synthesis and Reactions of 2,2-Dichlorocyclopropylmethyl-4-(2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl)benzoate with Secondary Amines
- Authors: Kolyamshin O.A.1, Mitrasov Y.N.2, Danilov V.A.1, Avruiskaya A.A.2
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Affiliations:
- I.N. Ulyanov Chuvash State University
- I. Ya. Yakovlev Chuvash State Pedagogical University
- Issue: Vol 89, No 9 (2019)
- Pages: 1740-1743
- Section: Article
- URL: https://journals.rcsi.science/1070-3632/article/view/223060
- DOI: https://doi.org/10.1134/S1070363219090020
- ID: 223060
Cite item
Abstract
The reaction of potassium 4-aminobenzoate with 2-bromomethyl-1,1-dichlorocyclopropane proceeds regioselectively with the retention of a three-membered ring and leads to the formation of 2,2-dichlorocyclo-propylmethyl 4-aminobenzoate. The reaction of 2,2-dichlorocyclopropylmethyl 4-aminobenzoate with maleic anhydride and intramolecular cyclization of the resulting amide in the presence of p-toluenesulfonic acid yields 2,2-dichlorocyclopropylmethyl-4-(2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl)benzoate. Secondary amines are attached at the double bond of the synthesized maleimide with the formation of 2,2-dichlorocyclopropylmethyl-4-[(3-R2N-2,5-dioxo-2,3,4,5-tetrahydro-1H-pyrrolyl)]benzoates.
About the authors
O. A. Kolyamshin
I.N. Ulyanov Chuvash State University
Author for correspondence.
Email: oleg.kolyamshin@yandex.ru
Russian Federation, Moskovskii pr. 15, Cheboksary, 428015
Yu. N. Mitrasov
I. Ya. Yakovlev Chuvash State Pedagogical University
Email: oleg.kolyamshin@yandex.ru
Russian Federation, Cheboksary
V. A. Danilov
I.N. Ulyanov Chuvash State University
Email: oleg.kolyamshin@yandex.ru
Russian Federation, Moskovskii pr. 15, Cheboksary, 428015
A. A. Avruiskaya
I. Ya. Yakovlev Chuvash State Pedagogical University
Email: oleg.kolyamshin@yandex.ru
Russian Federation, Cheboksary