A CONVENIENT AND EFFICIENT SYNTHESIS OF BENZOTRIAZOLES AND BENZISOXAZOLINES USING ANEW HYPERVALENT IODINE-BENZYNE PRECURSOR

Reaction of (phenyl)[o-(trimethylsilyl)phenyl]iodonium triflate with organic azides and nitrones using Bu 4 NF gave benzotriazoles and benzisoxazolines in high yields, respectively. This reaction indicates that benzyne is generated under mild conditions and efficiently trapped with the 1,3-dipoles to give heterocyclic compounds. Recently much attention has been paid to the use of hypervalent iodine compounds in organic synthesis (1-7). Previously we have found that (phenyl)[o-(trimethylsilyl)phenyl]iodonium triflate (1) acts as an excellent benzyne precursor and generates benzyne quantitatively by a simple treatment of o(trimethylsilyl)phenyliodonium triflate 1 with Bu 4 NF under very mild conditions as shown in Scheme 1 (8). The merits of the use of the hypervalent iodine-benzyne precursor 1 includes (a) the stability of the precursor 1, (b) no requirement of a strong base or high temperature, and (c) the quantitative generation of benzyne under mild conditions. If the hypervalent iodine-benzyne precursor 1 can be applied to the reactions with 1,3-dipoles such as azides and nitrones, the reaction of 1 will provides a useful methodology for synthesis of heterocyclic skeletons. In this paper, we report an efficient and convenient synthesis of benzotriazoles and benzisoxazolines by means of the hypervalent iodine-benzyne precursor 1. 1 100% Scheme 1.

• Publication year

  1998

• Venue

  Heterocyclic Communications

• Publication date

  Unknown publication date

• Fields of study

  Chemistry

• Identifiers
  DOI 10.1515/HC.1998.4.3.205
• External record

  Open on Semantic Scholar

• Source metadata

  Semantic Scholar

• No claims are published for this paper.

• No concepts are published for this paper.

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