Synthetic and mechanistic studies on 2,3-dihydrobenzo[b][1,4]oxaselenines formation from selenocyanates

MARÍA N. CHAO; SERGIO H. SZAJNMAN; MAURICIO CATTANEO; JONATHAN SANCHEZ GONZALEZ; SERGIO M. BONESI; JUAN B. RODRIGUEZ

SYNTHESIS-STUTTGART

GEORG THIEME VERLAG KG

Año: 2020

0039-7881

An expedient preparation of selenium-containing heterocycles via a m-chloroperbenzoic acid mediated seleno-annulation starting from selenocyanate derivatives is described. In spite of its significance, this cyclization reaction is virtually understudied not only from the point of view of its scope, but also from the mechanistic aspects associated to this remarkable transformation. In this sense, several selenocyanate and thiocyanate derivatives bearing an aromatic ring were evaluated as substrates under different reaction conditions of this interesting cyclization yielding important insights on its scope as well as relevant information on the reaction mechanism.