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

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-o...

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Published inJournal of organic chemistry Vol. 86; no. 15; pp. 10368 - 10379
Main Authors Golubev, Artem A, Agafonova, Anastasiya V, Smetanin, Ilia A, Rostovskii, Nikolai V, Khlebnikov, Alexander F, Bunev, Alexander S, Novikov, Mikhail S
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 06.08.2021
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
CYCLOADDITION
ISOXAZOLES
DESIGN
DISCOIPYRROLES
ISOMERIZATION
DIPHENYLCYCLOPROPENONE
INHIBITORS
CHLORINATION
CHLORIDE
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Summary: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.
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ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.1c01070