Unexpected synthesis of 3-imino-2-(pyrrol-2-yl) isatogen derivatives affords facile access to a 2-pyrrolyl isatogen

Date

2017

Authors

Kirk, Nicholas
Sansom, Geraud N
Sudta, Pichit
Suksamrarn, Sunit
Willis, Anthony
Bremner, John B
Kelso, Michael

Journal Title

Journal ISSN

Volume Title

Publisher

Taylor & Francis Group

Abstract

2-Aryl isatogens and their 3-imino derivatives have been extensively studied but to date there have been no reported variants carrying pyrrolyl substituents at the 2-position. This study describes the unexpected synthesis of two novel 3-imino-2-(pyrrol-2-yl) isatogen derivatives upon attempted amide couplings with (E)- or (Z)-3-(3,5-dimethyl-1H-pyrrol-2-yl)-2-(2-nitrophenyl)acrylic acids and p-phenylenediamines in the presence of uronium-based coupling reagents. Imine hydrolysis of one derivative under mild acid conditions afforded a 2-pyrrolyl isatogen in high yield. The compound showed potent in vitro antiplasmodial activity against Plasmodium falciparum

Description

Keywords

Antiplasmodial, 3-imino isatogen, N,N-dimethyl-pphenylenediamine, 2-pyrrolyl isatogen, p-phenylenediamine

Citation

Source

Synthetic Communications

Type

Journal article

Book Title

Entity type

Access Statement

License Rights

DOI

10.1080/00397911.2016.1249290

Restricted until

2099-12-31