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

Journal Article


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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.

Authors


  •   Kirk, Nicholas (external author)
  •   Sansom, Geraud (external author)
  •   Sudta, Pichit (external author)
  •   Suksamrarn, Sunit (external author)
  •   Willis, Anthony C. (external author)
  •   Bremner, John B.
  •   Kelso, Michael J.

Publication Date


  • 2017

Citation


  • 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.

Scopus Eid


  • 2-s2.0-85001022754

Ro Full-text Url


  • http://ro.uow.edu.au/cgi/viewcontent.cgi?article=1986&context=ihmri

Ro Metadata Url


  • http://ro.uow.edu.au/ihmri/961

Number Of Pages


  • 5

Start Page


  • 62

End Page


  • 67

Volume


  • 47

Issue


  • 1

Place Of Publication


  • United States

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.

Authors


  •   Kirk, Nicholas (external author)
  •   Sansom, Geraud (external author)
  •   Sudta, Pichit (external author)
  •   Suksamrarn, Sunit (external author)
  •   Willis, Anthony C. (external author)
  •   Bremner, John B.
  •   Kelso, Michael J.

Publication Date


  • 2017

Citation


  • 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.

Scopus Eid


  • 2-s2.0-85001022754

Ro Full-text Url


  • http://ro.uow.edu.au/cgi/viewcontent.cgi?article=1986&context=ihmri

Ro Metadata Url


  • http://ro.uow.edu.au/ihmri/961

Number Of Pages


  • 5

Start Page


  • 62

End Page


  • 67

Volume


  • 47

Issue


  • 1

Place Of Publication


  • United States