Preparation of 8-amido-2-dimethylamino-1, 2, 3, 4-tetrahydro-2-dibenzofurans and several fluorinated derivatives via [3, 3]-sigmatropic rearrangement of O-aryloximes

…, KT Ryter, AJ Sampognaro, SW Tregay…

Index: Guzzo, Peter R.; Buckle, Ronald N.; Chou, Ming; Dinn, Sean R.; Flaugh, Michael E.; Kiefer Jr., Anton D.; Ryter, Kendal T.; Sampognaro, Anthony J.; Tregay, Steven W.; Xu, Yao-Chang Journal of Organic Chemistry, 2003 , vol. 68, # 3 p. 770 - 778

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Citation Number: 23

Abstract

Methodology to prepare 8-amido-2-amino-1, 2, 3, 4-tetrahydro-2-dibenzofurans, analogues with a fluorine substituent incorporated in the 6-, 7-, and 9-positions, and a difluorinated analogue with fluorines in the 6-and 9-positions is described. The tetrahydrodibenzofuran ring systems are prepared by acid-catalyzed [3, 3]-sigmatropic rearrangement of O- aryloximes. Regioselective reactions to prepare the requisite O-aryloxime intermediates ...