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Nitrogen is an essential element in biological systems, forming a crucial component of proteins, nucleic acids, and other cellular constituents. Many bacteria and archaea acquire nitrogen in the form of nitrate (NO₃⁻) or ammonia (NH₃), which are then assimilated into biomolecules through specific enzymatic pathways.Assimilatory Nitrate ReductionWhen nitrate enters the cell, it undergoes a two-step reduction process known as assimilatory nitrate reduction. Initially, the enzyme...
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The reaction of weakly electrophilic aryldiazonium (also called arenediazonium) salts with highly activated aromatic compounds leads to the formation of products with an —N=N— link, called an azo linkage. This reaction, presented in Figure 1, is known as diazo coupling and occurs without the loss of the nitrogen atoms of the aryldiazonium salt. Highly activated aromatic compounds such as phenols or arylamines favor the diazo coupling reaction. The coupling generally occurs at the...
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DDQ in mechanochemical C-N coupling reactions.

Shyamal Kanti Bera1, Rosalin Bhanja1, Prasenjit Mal1

  • 1School of Chemical Sciences, National Institute of Science Education and Research (NISER), An OCC of Homi Bhabha National Institute, Bhubaneswar, PO Bhimpur-Padanpur, Via Jatni, District Khurda, Odisha 752050, India.

Beilstein Journal of Organic Chemistry
|June 16, 2022
PubMed
Summary

This study introduces 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) as a novel reagent for synthesizing benzimidazoles and quinazolinones. These compounds are efficiently produced via C-N coupling under solvent-free mechanochemical conditions.

Keywords:
1H-benzo[d]imidazoleC(sp2)–H amidationDDQball millmechanochemistryquinazolin-4(3H)-one

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry
  • Green Chemistry

Background:

  • 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) is a well-established oxidant.
  • Efficient synthesis of heterocyclic compounds like benzimidazoles and quinazolinones is crucial in medicinal chemistry.

Purpose of the Study:

  • To explore the utility of DDQ in C-N coupling reactions.
  • To develop a solvent-free mechanochemical method for synthesizing 1,2-disubstituted benzimidazoles and quinazolin-4(3H)-ones.

Main Methods:

  • Utilizing DDQ as an oxidant under solvent-free mechanochemical (ball milling) conditions.
  • Employing intramolecular C(sp2)-H amidation of N-(2-(arylideneamino)phenyl)-p-toluenesulfonamides.
  • One-pot coupling of 2-aminobenzamides with aryl/alkyl aldehydes.

Main Results:

  • Successful synthesis of 1,2-disubstituted benzimidazoles via intramolecular C-N coupling.
  • Efficient preparation of substituted quinazolin-4(3H)-one derivatives through one-pot intermolecular coupling.
  • High yields achieved for both reaction pathways under optimized conditions.

Conclusions:

  • DDQ is a versatile reagent for mechanochemical C-N coupling reactions.
  • The developed method offers a green and efficient route to important heterocyclic scaffolds.
  • This approach provides a valuable tool for the synthesis of benzimidazoles and quinazolinones.