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

Authors

Nicholas Kirk, University of WollongongFollow
Geraud Sansom, University of WollongongFollow
Pichit Sudta, Phetchaburi Rajabhat University, Srinakharinwirot University
Sunit Suksamrarn, Srinakharinwirot University
Anthony C. Willis, Australian National University
John B. Bremner, University of WollongongFollow
Michael J. Kelso, University of WollongongFollow

RIS ID

111132

Publication Details

Kirk, N. S., Sansom, G. N., Sudta, P., Suksamrarn, S., Willis, A. C., Bremner, J. B. & Kelso, M. J. (2017). Unexpected synthesis of 3-imino-2-(pyrrol-2-yl) isatogen derivatives affords facile access to a 2-pyrrolyl isatogen. Synthetic Communications: an international journal for rapid communication of synthetic organic chemistry, 47 (1), 62-67.

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.