Unexpected synthesis of 3-imino-2-(pyrrol-2-yl) isatogen derivatives affords facile access to a 2-pyrrolyl isatogen. Issue 1 (2nd January 2017)

• Record Type: Journal Article
• Authors: Kirk, Nicholas S.; Sansom, Geraud N.; Sudta, Pichit; Suksamrarn, Sunit; Willis, Anthony C.; Bremner, John B.; Kelso, Michael J.
• Is Part Of: Synthetic communications. Volume 47:Issue 1(2017)
• Page Start: 62
• Page End: 67
• Publication Date: 2017-01-02
• Subjects: Antiplasmodial -- 3-imino isatogen -- N, N-dimethyl-p-phenylenediamine -- 2-pyrrolyl isatogen -- p-phenylenediamine; Organic compounds -- Synthesis -- Periodicals; Chemistry, Organic; Synthesis; 547.205
• DOI: 10.1080/00397911.2016.1249290
• Languages: English
• ISSNs: 0039-7911

Abstract

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-1 H -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. GRAPHICAL ABSTRACT: