Tetrahedron

… and dihydrobenzopyrans (chromans) based on the intramolecular trapping by alcohols of benzynes generated from 7-substituted-1-aminobenzotriazoles

MA Birkett, DW Knight, PB Little, MB Mitchell

Index: Birkett, Michael A.; Knight, David W.; Little, Paul B.; Mitchell, Michael B. Tetrahedron, 2000 , vol. 56, # 7 p. 1013 - 1023

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Citation Number: 40

Abstract

1-Aminobenzotriazoles 9 having 7-hydroxyalkyl substituents are efficiently converted into the corresponding benzynes 4 when treated with N-iodosuccinimide which then undergo highly efficient intramolecular trapping by the pendant hydroxyl groups leading to dihydrobenzofurans 24–26 and dihydrobenzopyrans (chromans) 27, with incorporation of a synthetically useful iodine atom adjacent to the new ether bond, which allows subsequent ...