The Journal of organic chemistry

Synthesis of acridines by the [4+ 2] annulation of arynes and 2-aminoaryl ketones

DC Rogness, RC Larock

Index: Rogness, Donald C.; Larock, Richard C. Journal of Organic Chemistry, 2010 , vol. 75, # 7 p. 2289 - 2295

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Citation Number: 56

Abstract

In 2005, Kim et al.(28) reported the synthesis of acridines using 5-arylthianthrenium perchlorates as benzyne precursors to affect [4 + 2] annulations with ortho-aminoaryl ketones, esters, and aldehydes (eq 3). Although the scope of this methodology appears fairly broad, and the yields are generally good, some drawbacks to this methodology are evident. Not only is there no commercial source for Kim's benzyne precursor, but its synthesis requires the use of a highly ...