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

Nicholas S. Kirk; Geraud N. Sansom; Pichit Sudta; Sunit Suksamrarn; Anthony C. Willis; John B. Bremner; Michael J. Kelso

doi:10.1080/00397911.2016.1249290

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

Nicholas S. Kirk, Geraud N. Sansom, Pichit Sudta, Sunit Suksamrarn, Anthony C. Willis, John B. Bremner, Michael J. Kelso^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

3 Citations (Scopus)

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.

Original language	English
Pages (from-to)	62-67
Number of pages	6
Journal	Synthetic Communications
Volume	47
Issue number	1
DOIs	https://doi.org/10.1080/00397911.2016.1249290
Publication status	Published - 2017

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10.1080/00397911.2016.1249290

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

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.",

keywords = "2-pyrrolyl isatogen, 3-imino isatogen, Antiplasmodial, N,N-dimethyl-p-phenylenediamine, p-phenylenediamine",

author = "Kirk, {Nicholas S.} and Sansom, {Geraud N.} and Pichit Sudta and Sunit Suksamrarn and Willis, {Anthony C.} and Bremner, {John B.} and Kelso, {Michael J.}",

note = "Publisher Copyright: {\textcopyright} 2017, Copyright {\textcopyright} Taylor & Francis Group, LLC.",

year = "2017",

doi = "10.1080/00397911.2016.1249290",

language = "English",

volume = "47",

pages = "62--67",

journal = "Synthetic Communications",

issn = "0039-7911",

publisher = "Taylor and Francis Ltd.",

number = "1",

}

TY - JOUR

T1 - Unexpected synthesis of 3-imino-2-(pyrrol-2-yl) isatogen derivatives affords facile access to a 2-pyrrolyl isatogen

AU - Kirk, Nicholas S.

AU - Sansom, Geraud N.

AU - Sudta, Pichit

AU - Suksamrarn, Sunit

AU - Willis, Anthony C.

AU - Bremner, John B.

AU - Kelso, Michael J.

PY - 2017

Y1 - 2017

N2 - 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.

AB - 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.

KW - 2-pyrrolyl isatogen

KW - 3-imino isatogen

KW - Antiplasmodial

KW - N,N-dimethyl-p-phenylenediamine

KW - p-phenylenediamine

UR - http://www.scopus.com/inward/record.url?scp=85001022754&partnerID=8YFLogxK

U2 - 10.1080/00397911.2016.1249290

DO - 10.1080/00397911.2016.1249290

M3 - Article

SN - 0039-7911

VL - 47

SP - 62

EP - 67

JO - Synthetic Communications

JF - Synthetic Communications

IS - 1

ER -

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

Abstract

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