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Selective and Stepwise Functionalization of the Pyridazine Scaffold by Using Thio-Substituted Pyridazine Building

Clémence Hamze1, Julie Brossier1, Konstantin Karaghiosoff1

  • 1Department of Chemistry, Ludwig-Maximilians University, Butenandtstraße 5-13, Haus F, 81377, Munich, Germany.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|August 3, 2023
PubMed
Summary

This study introduces a new method for regioselectively functionalizing pyridazine rings. The developed approach enables the synthesis of complex N-heterocycles, expanding synthetic chemistry possibilities.

Keywords:
N-heterocyclescross-couplingmagnesium amidesmetalationpyridazine

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Area of Science:

  • Organic Chemistry
  • Heterocyclic Chemistry

Background:

  • Pyridazine scaffolds are important in medicinal chemistry.
  • Developing efficient functionalization methods for pyridazines is crucial.

Purpose of the Study:

  • To develop a regioselective tri- and tetra-functionalization strategy for pyridazine scaffolds.
  • To explore the synthesis of novel N-heterocycles from functionalized pyridazines.

Main Methods:

  • Selective metalations using TMPMgCl·LiCl.
  • Catalyst-tuned cross-coupling reactions with arylzinc halides.
  • Synthesis of thieno[2,3-c]pyridazines and 1H-pyrazolo[3,4-c]pyridazines.

Main Results:

  • Achieved regioselective tri- and tetra-functionalization of pyridazines.
  • Successfully synthesized functionalized pyridazine building blocks.
  • Converted pyridazine derivatives into complex N-heterocycles.

Conclusions:

  • The described method provides efficient access to diversely functionalized pyridazines.
  • This work expands the synthetic utility of pyridazine scaffolds.
  • The methodology facilitates the construction of valuable N-heterocyclic compounds.