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Peer-reviewedCC BY-NC-ND 4.0Organic Chemistry Frontiers

A radical cascade via dearomative ipso -annulation of indolyl N -cyanamides: access to spiro[indoline-pyrroloquinazolinones]

  • Anootha Neeliveettil
  • Jannatul Islam
  • Luc Neuville
  • Geraldine Masson
  • Chada Raji Reddy
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Abstract

This study reports a novel acyl-radical-promoted cascade annulation of indolyl N-cyanamides to afford spiro[indoline-pyrrolo[2,1-b]quinazolinone] frameworks. The conversion proceeds through sequential acyl radical addition, dearomative ipso-annulation by the capture of the C3-radical with an N-cyano group and quinazolinone ring formation in the presence of an oxidant in a single operation. This protocol features broad substrate scope with good functional-group tolerance and represents a highly diastereo- selective atom- and step-economical platform for the assembly of complex spirocycles integrating two bioactive scaffolds, quinazolinone and indoline, from a linear precursor.

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Cite

BibTeXRIS
BibTeX
@article{neeliveettil2026radical,
  title = {{A radical cascade via dearomative ipso -annulation of indolyl N -cyanamides: access to spiro[indoline-pyrroloquinazolinones]}},
  author = {Anootha Neeliveettil and Jannatul Islam and Luc Neuville and Geraldine Masson and Chada Raji Reddy},
  journal = {Organic Chemistry Frontiers},
  year = {2026},
  month = sep,
  doi = {10.1039/d6qo00923a},
  url = {https://hal.science/hal-05763576v1},
  note = {CC BY-NC-ND 4.0},
}
RIS
TY  - JOUR
TI  - A radical cascade via dearomative ipso -annulation of indolyl N -cyanamides: access to spiro[indoline-pyrroloquinazolinones]
AU  - Anootha Neeliveettil
AU  - Jannatul Islam
AU  - Luc Neuville
AU  - Geraldine Masson
AU  - Chada Raji Reddy
PY  - 2026
DA  - 2026/09/03
JO  - Organic Chemistry Frontiers
DO  - 10.1039/d6qo00923a
UR  - https://hal.science/hal-05763576v1
AB  - This study reports a novel acyl-radical-promoted cascade annulation of indolyl N-cyanamides to afford spiro[indoline-pyrrolo[2,1-b]quinazolinone] frameworks. The conversion proceeds through sequential acyl radical addition, dearomative ipso-annulation by the capture of the C3-radical with an N-cyano group and quinazolinone ring formation in the presence of an oxidant in a single operation. This protocol features broad substrate scope with good functional-group tolerance and represents a highly diastereo- selective atom- and step-economical platform for the assembly of complex spirocycles integrating two bioactive scaffolds, quinazolinone and indoline, from a linear precursor.
SN  - 2052-4110
SN  - 2052-4129
ER  -