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

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Issued Date

2017

Resource Type

Article

File Type

application/pdf

ISSN

397911

DOI

10.1080/00397911.2016.1249290

Other identifier(s)

2-s2.0-85001022754

Rights Holder(s)

Scopus

Bibliographic Citation

Synthetic Communications. Vol 47, No.1 (2017), p.62-67

Suggested Citation

Kirk N.S., Sansom G.N., Sudta P., Suksamrarn S., Willis A.C., Bremner J.B., Kelso M.J. Unexpected synthesis of 3-imino-2-(pyrrol-2-yl) isatogen derivatives affords facile access to a 2-pyrrolyl isatogen. Synthetic Communications. Vol 47, No.1 (2017), p.62-67. doi:10.1080/00397911.2016.1249290 Retrieved from: https://hdl.handle.net/20.500.14740/4667

Title

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

Author(s)

Kirk N.S.
 Sansom G.N.
 Sudta P.
 Suksamrarn S.
 Willis A.C.
 Bremner J.B.
 Kelso M.J.

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. © 2017, Copyright © Taylor & Francis Group, LLC.

Subject(s)

Amide
 Antiprotozoal agent
 Imine
 Isatogen derivative
 Unclassified drug
 Antiprotozoal activity
 Article
 Crystal structure
 Drug synthesis
 Hydrogen bond
 Hydrolysis
 In vitro study
 Nonhuman
 Plasmodium falciparum

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URI

https://hdl.handle.net/20.500.14740/4667

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Scopus: Year 1983-2021

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