Issue 15, 2000

1-Aminobenzotriazole functionalisation using directed metallation: new routes to chromanes and chromenes using intramolecular benzyne trapping by alcohols

Abstract

Metallation of 1-(tert-butoxycarbonylamino)benzotriazole 8 leads to the dianionic species 9 which undergoes smooth reactions with a range of electrophiles, under appropriate conditions. The derived iodide 30 undergoes efficient Sonogashira coupling with a range of alk-1-yn-3-ols to provide the expected arylalkynes 33, total or partial reduction of which leads to the arylpropanols 34 and the (Z )-allylic alcohols 40 respectively. N-Deprotection and exposure to N-iodosuccinimide then led to smooth benzyne generation and intramolecular trapping by the hydroxy functions with iodine incorporation to give the iodochromanes 35 and iodochromenes 41 respectively, in respectable overall yields.

Article information

Article type
Paper
Submitted
07 Mar 2000
Accepted
07 Apr 2000
First published
30 Jun 2000

J. Chem. Soc., Perkin Trans. 1, 2000, 2343-2355

1-Aminobenzotriazole functionalisation using directed metallation: new routes to chromanes and chromenes using intramolecular benzyne trapping by alcohols

D. W. Knight and P. B. Little, J. Chem. Soc., Perkin Trans. 1, 2000, 2343 DOI: 10.1039/B001834L

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