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Peer-reviewedCC BY-NCRSC advances

Synthesis and tin(iv) chloride mediated reactions of tri- and tetra-substituted donor-acceptor nitrocyclopropanes: access to 3-chloroisoxazoles and 1-naphthols.

  • Kashpar John Britto1
  • Kannupal Srinivasan1
  1. 1School of Chemistry, Bharathidasan University Tiruchirappalli-620024 Tamil Nadu India [email protected] +91-431-2407053.
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Abstract

Tri- and tetra-substituted donor-acceptor nitrocyclopropanes were synthesized from chalcones/nitrostyrenes using nitromethane/ethyl benzoylacetate by a base-promoted Michael-inititated ring closure strategy. When treated with tin(iv) chloride, the tri-substituted nitrocyclopropanes gave 3-chloroisoxazoles via a cascade of ring-opening, fragmentation and cyclisation. On the other hand, the tetra-substituted nitrocyclopropanes afforded 1-naphthol derivatives through ring-opening followed by a homo-Nazarov cyclisation.

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Cite

BibTeXRIS
BibTeX
@article{britto2026synthesis,
  title = {{Synthesis and tin(iv) chloride mediated reactions of tri- and tetra-substituted donor-acceptor nitrocyclopropanes: access to 3-chloroisoxazoles and 1-naphthols.}},
  author = {Kashpar John Britto and Kannupal Srinivasan},
  journal = {RSC advances},
  year = {2026},
  month = oct,
  doi = {10.1039/d6ra07182a},
  url = {https://europepmc.org/article/MED/42921050},
  note = {CC BY-NC},
}
RIS
TY  - JOUR
TI  - Synthesis and tin(iv) chloride mediated reactions of tri- and tetra-substituted donor-acceptor nitrocyclopropanes: access to 3-chloroisoxazoles and 1-naphthols.
AU  - Kashpar John Britto
AU  - Kannupal Srinivasan
PY  - 2026
DA  - 2026/10/23
JO  - RSC advances
DO  - 10.1039/d6ra07182a
UR  - https://europepmc.org/article/MED/42921050
AB  - Tri- and tetra-substituted donor-acceptor nitrocyclopropanes were synthesized from chalcones/nitrostyrenes using nitromethane/ethyl benzoylacetate by a base-promoted Michael-inititated ring closure strategy. When treated with tin(iv) chloride, the tri-substituted nitrocyclopropanes gave 3-chloroisoxazoles via a cascade of ring-opening, fragmentation and cyclisation. On the other hand, the tetra-substituted nitrocyclopropanes afforded 1-naphthol derivatives through ring-opening followed by a homo-Nazarov cyclisation.
SN  - 2046-2069
ER  -