The Journal of Organic Chemistry

Competing Pathways in the Azomethine Ylide Route to Indoloquinones: An Improved Procedure for the Generation of a Transient 4-Oxazoline from the Oxazolium Salt

E Vedejs, SD Monahan

Index: Vedejs, Edwin; Monahan, Sean D. Journal of Organic Chemistry, 1997 , vol. 62, # 14 p. 4763 - 4769

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Citation Number: 22

Abstract

Azomethine ylide generation from the oxazolium salt 22 and PhSiH3/CsF affords complex products derived from the initial cycloadduct 23 via three competing pathways. Colorless intermediates 24-27 have been detected, and their oxidation products 10, 28, and 29 have been identified. Nucleophilic activation of the oxazolium salt 22 is reported using the organic- soluble benzyltrimethylammonium cyanide. This variation affords the unstable ...

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