4.8 Article

N-Iodosuccinimide-Promoted [3+2] Annulation Reaction of Aryldiazonium Salts with Guanidines To Construct Aminotetrazoles

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ORGANIC LETTERS
卷 23, 期 22, 页码 8894-8898

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AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c03395

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资金

  1. National Key Research & Development Program of China [2019YFA0905100]
  2. National Natural Science Foundation of China [21772142, 21901181, 21961142015]

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A novel N-iodosuccinimide-promoted [3 + 2] annulation reaction has been developed for the synthesis of 2-aryl-5-amino-2H-tetrazoles, which were previously difficult to access. The reaction utilizes readily available starting materials, operates under metal-free conditions, and exhibits broad functional group compatibility. The utility of this protocol is demonstrated through various derivatization reactions such as coupling, annulation, deamination, and denitrogenation.
A N-iodosuccinimide (NIS)-promoted [3 + 2] annulation reaction of aryldiazonium salts with guanidines has been developed for the construction of previously elusive 2-aryl-5-amino-2H-tetrazoles. This transformation takes advantage of readily available starting materials, proceeds under metal-free, mild, and robust conditions, and holds broad functional group compatibility. The utility of this protocol is further manifested via coupling, annulation, deamination, and denitrogenation derivatizations.

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