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August 16, 2026Communications ChemistryOpen Access

Continuous-flow photogeneration of nitrosobenzaldehydes enables indazolone formation

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Authors

NLNicolas LeclercqDSDiana V. Silva-BrenesJMJean‐Christophe M. Monbaliu

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Overview

Chemical synthesis study demonstrates metal-free continuous-flow photogeneration of indazolones from o-nitrobenzyl alcohols, highlighting a sustainable path to biologically active heterocycles.

Key Points

  • To develop a mild, metal-free continuous-flow photochemical protocol for synthesizing biologically relevant indazolones from o-nitrobenzyl alcohols and primary amines.
  • Irradiated o-nitrobenzyl alcohols in ethanol at 365 nm (and substrate-matched wavelengths) inside continuous-flow reactors to generate o-nitrosobenzaldehydes in situ.
  • Coupled intermediate nitrosobenzaldehydes with primary amines through tandem condensation-cyclization sequences to form indazolone cores.
  • Evaluated reaction photophysics and substituent electronic effects using UV-visible spectroscopy and conceptual density functional theory (DFT).
  • Substrate reaction efficiency was found to be wavelength-dependent, where matching irradiation to substrate absorption minimized photodegradation and maximized nitroso intermediate generation.
  • Conceptual DFT analysis rationalized substituent electronic effects that govern both photophysical activation and polar condensation-cyclization reactivity.
  • The protocol demonstrated practical scalability in commercial continuous-flow reactors without requiring transition metal catalysts or harsh reagents.

Cite This Study

Leclercq et al. (2026) studied this question.

synapsesocial.com/papers/6a817a01f2fb91fc834ad7bdhttps://doi.org/10.1038/s42004-026-02146-9
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