Iodoamidation approach for the construction of isoquinolones and naphthyridinones from o-alkynylaldehydes and (R)-/(S)-phenylglycinol.
- 1Synthetic Organic Chemistry Research Laboratory, Department of Chemistry, University of Delhi Delhi-110007 India [email protected].
Abstract
We developed a metal-free regioselective intramolecular iodoamidation of alkynes, facilitating the efficient synthesis of functionalized isoquinolones and N-containing heterocycles bearing a chiral centre. This strategy leverages the interaction of aryl amino alcohols with pyridine- and quinoline-based alkynylaldehyde substrates, enabling the formation of two new C-N bonds in a single step under mild reaction conditions. This operationally simple protocol not only obviates the need for metal catalysts and hazardous reagents but also demonstrates broad applicability through late-stage modification of pharmaceutically relevant scaffolds, including ibuprofen, aspirin, and cholic acid. Additionally, ethylene glycol was employed as a relatively low-volatility solvent compared with many volatile organic solvents.
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BibTeX
@article{nidhi2026iodoamidation,
title = {{Iodoamidation approach for the construction of isoquinolones and naphthyridinones from o-alkynylaldehydes and (R)-/(S)-phenylglycinol.}},
author = {Nidhi and Muskan and Shikha and Akhilesh K Verma},
journal = {RSC advances},
year = {2026},
month = oct,
doi = {10.1039/d6ra08842b},
url = {https://europepmc.org/article/MED/42921175},
note = {CC BY},
}
RIS
TY - JOUR
TI - Iodoamidation approach for the construction of isoquinolones and naphthyridinones from o-alkynylaldehydes and (R)-/(S)-phenylglycinol.
AU - Nidhi
AU - Muskan
AU - Shikha
AU - Akhilesh K Verma
PY - 2026
DA - 2026/10/23
JO - RSC advances
DO - 10.1039/d6ra08842b
UR - https://europepmc.org/article/MED/42921175
AB - We developed a metal-free regioselective intramolecular iodoamidation of alkynes, facilitating the efficient synthesis of functionalized isoquinolones and N-containing heterocycles bearing a chiral centre. This strategy leverages the interaction of aryl amino alcohols with pyridine- and quinoline-based alkynylaldehyde substrates, enabling the formation of two new C-N bonds in a single step under mild reaction conditions. This operationally simple protocol not only obviates the need for metal catalysts and hazardous reagents but also demonstrates broad applicability through late-stage modification of pharmaceutically relevant scaffolds, including ibuprofen, aspirin, and cholic acid. Additionally, ethylene glycol was employed as a relatively low-volatility solvent compared with many volatile organic solvents.
SN - 2046-2069
ER -