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

Authors

  • Almir S. Gazizov  *

    A.E. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center, Russian Academy of Sciences, Arbuzova str., 8, Kazan, Russian Federation   Email: agazizov@iopc.ru
  • 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: agazizov@iopc.ru
  • 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: agazizov@iopc.ru
  • 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: agazizov@iopc.ru
  • 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: agazizov@iopc.ru
  • 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: agazizov@iopc.ru

This work was supported by the Russian Science Foundation (Grant No. 16-13-10023).
Further Information

Publication History

Received: 08 September 2017

Accepted after revision: 13 October 2017

Publication Date:
13 November 2017 (online)


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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