Synlett 2018; 29(04): 467-472
DOI: 10.1055/s-0036-1590954
letter
© Georg Thieme Verlag Stuttgart · New York

Acid-Mediated C–N Bond Cleavage in 1-Sulfonylpyrrolidines: An Efficient Route towards Dibenzoxanthenes, Diarylmethanes, and Resorcinarenes

A.E. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center, Russian Academy of Sciences, Arbuzova str., 8, Kazan, Russian Federation   eMail: [email protected]
,
Andrey V. Smolobochkin
A.E. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center, Russian Academy of Sciences, Arbuzova str., 8, Kazan, Russian Federation   eMail: [email protected]
,
Ekaterina A. Anikina
A.E. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center, Russian Academy of Sciences, Arbuzova str., 8, Kazan, Russian Federation   eMail: [email protected]
,
Anna G. Strelnik
A.E. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center, Russian Academy of Sciences, Arbuzova str., 8, Kazan, Russian Federation   eMail: [email protected]
,
Alexander R. Burilov
A.E. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center, Russian Academy of Sciences, Arbuzova str., 8, Kazan, Russian Federation   eMail: [email protected]
,
Michail A. Pudovik
A.E. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center, Russian Academy of Sciences, Arbuzova str., 8, Kazan, Russian Federation   eMail: [email protected]
› Institutsangaben
This work was supported by the Russian Science Foundation (Grant No. 16-13-10023).
Weitere Informationen

Publikationsverlauf

Received: 08. September 2017

Accepted after revision: 13. Oktober 2017

Publikationsdatum:
13. November 2017 (online)


Abstract

The rare example of pyrrolidine C–N bond cleavage in 1-sulfonylpyrrolidines in acidic media in the presence of phenols is reported. The reaction proceeds under mild conditions and provides a convenient route to otherwise hardly accessible and previously unknown dibenzoxanthenes, diarylbutanes, and resorcinarenes having a sulfonylamide moiety.

Supporting Information

 
  • References and Notes

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