Synthesis of Pyrroles via Consecutive 6π-Electrocyclization/Ring-Contraction of Sulfilimines.

Journal of the American Chemical Society
Franz-Lucas HautThomas Magauer

Abstract

We present a modular, synthetic entry to polysubstituted pyrroles employing readily available 2,5-dihydrothiophenes. Ring-opening of the heterocycle provides access to a panel of 1,3-dienes which undergo pyrrole formation in the presence of inexpensive chloramine-T trihydrate. The transformation is conducted in an open flask and proceeds at ambient temperatures (23 °C) in nondry solvents. A careful adjustment of the electronics and sterics of the 1,3-diene precursor allows for the isolation of key intermediates. DFT studies identified a reaction mechanism that features a 6π-electrocyclization of a sulfilimine intermediate followed by spontaneous ring-contraction to reveal the pyrrole skeleton.

References

Jun 30, 2001·The Journal of Organic Chemistry·A L Marzinzik, K B Sharpless
Jan 9, 2003·Progress in Medicinal Chemistry·Bruce D Roth
Nov 6, 2004·The Journal of Organic Chemistry·Vildan Adar GunerIan W Davies
Jul 14, 2006·Chemical Reviews·Guy R Humphrey, Jeffrey T Kuethe
Jul 29, 2006·The Journal of Organic Chemistry·Tang-Qing YuQing-Xiang Guo
Sep 12, 2008·Angewandte Chemie·Lee M BishopDirk Trauner
Aug 7, 2010·Journal of the American Chemical Society·Takayuki KobatakeKoichiro Oshima
Jan 12, 2013·Chemical Reviews·Anton V GulevichVladimir Gevorgyan
May 6, 2015·Chemical Society Reviews·Vincent BizetCarsten Bolm
Jan 26, 2016·European Journal of Medicinal Chemistry·Somnath S Gholap
Dec 27, 2016·Frontiers in Microbiology·Jaafar Kilani, Sabine Fillinger
Jan 18, 2018·Journal of the American Chemical Society·Alexander W SchuppeTimothy R Newhouse
May 16, 2018·Journal of the American Chemical Society·Zachary W Davis-GilbertIan A Tonks
Aug 18, 2018·European Journal of Medicinal Chemistry·Shujauddin AhmadMuzaffar Iqbal
Nov 21, 2018·Food and Chemical Toxicology : an International Journal Published for the British Industrial Biological Research Association·T Tristan Brandhorst, Bruce S Klein
Aug 14, 2019·Journal of the American Chemical Society·Franz-Lucas HautThomas Magauer
Apr 8, 2020·Angewandte Chemie·Martin Breugst, Hans-Ulrich Reissig
May 13, 2020·Journal of the American Chemical Society·Yujing ZhouStephen L Buchwald
Jan 6, 2021·Journal of the American Chemical Society·Franz-Lucas HautThomas Magauer
Aug 10, 2021·Synthesis·Satish Chandra PhilkhanaRendy Kartika

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Citations

Aug 24, 2021·Accounts of Chemical Research·Ian A Tonks
Aug 31, 2021·Angewandte Chemie·Heng LiuQing-An Chen

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