Synthesis 2020; 52(11): 1643-1658
DOI: 10.1055/s-0039-1690800
paper
© Georg Thieme Verlag Stuttgart · New York

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

María N. Chao
a  Departamento 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
a  Departamento 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
b  INQUINOA-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
a  Departamento 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
c  Departamento 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
a  Departamento 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
› Author Affiliations
This work was supported by grants from Consejo Nacional de Investigaciones Científicas y Técnicas (PIP 112-201501-00631CO) to J.B.R., Agencia Nacional de Promoción Científica y Tecnológica (PICT 2015 No 1349) to J.B.R. and (PICT 2016 No 3224) to M.C., and Universidad de Buenos Aires (20020170100067BA) to J.B.R.
Further Information

Publication History

Received: 09 December 2019

Accepted after revision: 29 December 2019

Publication Date:
17 February 2020 (online)


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.

Supporting Information

 
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