29917-03-1Relevant articles and documents
Synthesis of Pyrroles via Consecutive 6π-Electrocyclization/Ring-Contraction of Sulfilimines
Haut, Franz-Lucas,Feichtinger, Niklas J.,Plangger, Immanuel,Wein, Lukas A.,Müller, Mira,Streit, Tim-Niclas,Wurst, Klaus,Podewitz, Maren,Magauer, Thomas
supporting information, p. 9002 - 9008 (2021/07/01)
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.
REACTIONEN VON THIOXOHETEROCYCLEN MIT N-CHLORAMIDEN I. N-(2-PYRIDYLTHIO)AMIDE
Boberg, Friedrich,Paetz, Andrea,Bruchmann, Bernd,Garming, Alfons
, p. 99 - 108 (2007/10/02)
N-(2-Pyridylthio)amides 7 and salts of them have been prepared from 2-thiopyridone (1) with sodium-N-chloro- or N,N-dichlorobenzenesulfonamides (3 or 4), N-chloro- or N,N-dichloro-o-nitrobenzamide (2e or 4e), N-chloro- or N,N-dichloroethylurethane (2f or 4f).Reactions of different amides 7 and the 13C- and 15N-NMR-spectra of N-(2-pyridylthio)-p-toluenesulfonamide (7b) prove the constitutions.