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Synfacts 2011(1): 0015-0015  
DOI: 10.1055/s-0030-1259198
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart ˙ New York

Benzofurans, Indoles, and Isoquinolones via Castro-Stephens and Heck Reactions

Contributor(s): Victor Snieckus, Matthew O. Kitching
R. Álvarez*, C. Martínez, Y. Madich, J. G. Denis, J. M. Aurrecoechea*, Á. R. de Lera*
Universidade de Vigo and Universidad del País Vasco, Bilbao, Spain
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Publikationsdatum:
21. Dezember 2010 (online)

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Significance

Reported is the synthesis of benzofurans A, indoles B, and isoquinolones C via a ­Sonogashira coupling and subsequent sequential Castro-Stephens and Heck strategy. In the case of the benzofuran synthesis, a detailed screen of catalyst, additives, base, temperature, and equivalents of alkene is described, which led to the ­optimum conditions as shown above. Substrate scope is examined, particularly the effects of ­varying the alkyne (R¹) and amide (R5) substituents, which shows good tolerance to modification.