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

doi:10.1055/s-0039-1690800

Synthesis, Table of Contents

Synthesis 2020; 52(11): 1643-1658
DOI: 10.1055/s-0039-1690800

paper

Synthetic and Mechanistic Studies on 2,3-Dihydrobenzo[b][1,4]-oxaselenines Formation from Selenocyanates

María N. Chao

^aDepartamento de Química Orgánica and UMYMFOR (CONICET–FCEyN), Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellón 2, Ciudad Universitaria, C1428EHA, Buenos Aires, Argentina Email: jbr@qo.fcen.uba.ar

,

Sergio H. Szajnman∗

^aDepartamento de Química Orgánica and UMYMFOR (CONICET–FCEyN), Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellón 2, Ciudad Universitaria, C1428EHA, Buenos Aires, Argentina Email: jbr@qo.fcen.uba.ar

,

Mauricio Cattaneo

^bINQUINOA-UNT-CONICET, Instituto de Química Física, Facultad de Bioquímica, Química y Farmacia Universidad Nacional de Tucumán, Ayacucho 471, T4000INI, San Miguel de Tucumán, Argentina

,

Jonathan Sanchez Gonzalez

^aDepartamento de Química Orgánica and UMYMFOR (CONICET–FCEyN), Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellón 2, Ciudad Universitaria, C1428EHA, Buenos Aires, Argentina Email: jbr@qo.fcen.uba.ar

,

Sergio M. Bonesi

^cDepartamento de Química Orgánica and CIHIDECAR (CONICET–FCEyN), Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellón 2, Ciudad Universitaria, C1428EHA, Buenos Aires, Argentina

,

Juan B. Rodriguez∗

^aDepartamento de Química Orgánica and UMYMFOR (CONICET–FCEyN), Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellón 2, Ciudad Universitaria, C1428EHA, Buenos Aires, Argentina Email: jbr@qo.fcen.uba.ar

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Abstract

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Abstract

An expedient preparation of selenium-containing heterocycles via an 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.

Key words

oxaselenines - selenocyanates - heterocycles - radical mechanism - electron transfer reaction

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References

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