The Journal of Organic Chemistry

A retro-Diels-Alder approach to oxazoles and imidazoles

MA Eissenstat, JD Weaver III

Index: Eissenstat, Michael A.; Weaver, John D. Journal of Organic Chemistry, 1993 , vol. 58, # 12 p. 3387 - 3390

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Citation Number: 22

Abstract

Heating N-acyl derivatives 4 of 3-endo-aminobicyclo [2.2. l] hept-5-en-2-end0-01 (3) at 185- 195 OC for 4-5 h provides oxazoles la-in 49-8895 yields. The reaction proceeds via initial dehydration to an oxazoline which undergoes retro-Diels-Alder reaction to provide the oxazole. Similarly, imidazoles 7a-f may be obtained in 40-79% yields by heating imidazolines 6a-f to effect the cycloreversion.

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