4.7 Article

I2-Mediated [3+2] annulation of methyl-azaarenes with alkyl 2-isocyanoacetates or amino acid ester hydrochlorides: selective synthesis of iodine-functionalized and non-iodine-functionalized fused imidazoles

Journal

ORGANIC CHEMISTRY FRONTIERS
Volume 9, Issue 5, Pages 1403-1409

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/d1qo01940f

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Funding

  1. National Natural Science Foundation of China [21702091]
  2. Science and Technology Innovation Development Plan of Yantai [2020MSGY114]
  3. Yantai Double Hundred Plan
  4. Graduate Innovation Foundation of Yantai University [YDYB2128]

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In this study, an I-2-mediated [3 + 2] annulation of methyl-azaarenes with alkyl 2-isocyanoacetates or amino acid ester hydrochlorides was demonstrated. This method allows for the selective synthesis of iodine-functionalized and non-iodine-functionalized fused imidazoles, with the potential for further chemical modifications of the iodine-functionalized products.
An I-2-mediated [3 + 2] annulation of methyl-azaarenes with alkyl 2-isocyanoacetates or amino acid ester hydrochlorides has been demonstrated. This strategy involves C equivalent to N bond cleavage of isocyanides and can selectively synthesize iodine-functionalized and non-iodine-functionalized fused imidazoles. Scaleup experiments and arylation, alkynylation, alkenylation and selenization of iodine-functionalized products demonstrated the potential applications of this reaction.

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