4.7 Article

Competing Intra- vs Intermolecular Nitrene Transfer in the [Au]-Catalysed Reaction of 2-Alkynylphenylazides

Journal

ADVANCED SYNTHESIS & CATALYSIS
Volume 364, Issue 6, Pages 1122-1133

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.202101412

Keywords

Gold Catalysis; Nitrene Transfer; Quinazoline; Anthranil and 1; 2-Benzisoxazole

Funding

  1. CSIR (India)
  2. DST-INSPIRE

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In this study, the possibility of interrupting the gold-catalysed intramolecular cyclization was explored in order to develop simple tools for product diversification. It was found that using 1,2-benzisoxazoles, intermolecular nitrene transfer competed with intramolecular azidoalkyne cyclization resulting in spiro indol-3-ylidene derivatives. However, when anthranil was present, both intra- and intermolecular nitrene transfer processes led to the same product indol-3-ylidene.
The possibility of interrupting the gold-catalysed intramolecular cyclization of 2-alkynylphenylazide derivatives, employing known nitrene transfer reagents such as anthranil and its isomer 1,2-benzisoxazole, has been attempted in search of developing simple tools for product diversification. With 1,2-benzisoxazoles, the intermolecular nitrene transfer leading to quinazoline is competitive with intramolecular azidoalkyne cyclization resulting in spiro indol-3-ylidene derivatives. However, in case of the reaction in the presence of anthranil, both intra- and intermolecular nitrene transfer processes result in the same product indol-3-ylidene.

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