The Journal of organic chemistry

A facile and efficient synthesis of thieno [2, 3-c] furans and furo [3, 4-b] indoles via a Pummerer-induced cyclization reaction

CO Kappe, A Padwa

Index: Kappe, C. Oliver; Padwa, Albert Journal of Organic Chemistry, 1996 , vol. 61, # 18 p. 6166 - 6174

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Citation Number: 41

Abstract

The α-thiocarbocation generated from the Pummerer reaction of an o-heteroaroyl- substituted sulfoxide is intercepted by the adjacent keto group to produce an α-thio- substituted heteroaromatic isobenzofuran. In the presence of a suitable dienophile, the reactive o-xylylene undergoes a Diels-Alder cycloaddition followed by an acid-catalyzed ring-opening and aromatization to give heteroaromatic naphthalene derivatives. This one- ...