A Hydroxypyrrole Approach to 2,2′-Bi(4-pyrrolin-3-ones) and Pyrrolone-Based α-Amino Esters

Artem A. Golubev, Anastasiya V. Agafonova, Ilia A. Smetanin, Nikolai V. Rostovskii, Alexander F. Khlebnikov, Alexander S. Bunev, Mikhail S. Novikov

Research output: Contribution to journalArticlepeer-review

Abstract

A high yield synthesis of 2-amino-4-pyrrolin-3-ones including 4-pyrrolin-3-one-based amino esters by the NBS- or TfCl-mediated reaction of 3-hydroxypyrroles with amines has been developed. The reaction of 3-hydroxypyrroles with triflyl chloride in the absence of amine affords 2,2′-bi(4-pyrrolin-3-ones) in excellent yields and diastereoselectivity. The relative configuration of stereocenters in these compounds can be changed from (2RS,2′RS) to (2RS,2′SR) by the action of NaH in THF, while the reverse stereoisomerization occurs in the presence of 2,5-lutidine in MeCN. Bi(4-pyrrolin-3-ones) also can be converted to 2-amino-4-pyrrolin-3-ones in excellent yields. Bi(4-pyrrolin-3-ones) and 2-amino-4-pyrrolin-3-ones were evaluated for their antiproliferative activity toward four human tumor cell lines.

Original languageEnglish
Pages (from-to)10368-10379
Number of pages12
JournalJournal of Organic Chemistry
DOIs
StatePublished - 6 Aug 2021

Scopus subject areas

  • Organic Chemistry

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