18836-83-4Relevant academic research and scientific papers
Primary Sulfonamide Functionalization via Sulfonyl Pyrroles: Seeing the N?Ts Bond in a Different Light
Ozaki, Tomoya,Yorimitsu, Hideki,Perry, Gregory J. P.
supporting information, p. 15387 - 15391 (2021/10/04)
Despite common occurrence in molecules of value, methods for transforming sulfonamides are distinctly lacking. Here we introduce easy-to-access sulfonyl pyrroles as synthetic linchpins for sulfonamide functionalization. The versatility of the sulfonyl pyrrole unit is shown by generating a variety of products through chemical, electrochemical and photochemical pathways. Preliminary results on the direct functionalization of primary sulfonamides are also provided, which may lead to new modes of activation.
Synthesis of N -Sulfonyl- and N -Acylpyrroles via a Ring-Closing Metathesis/Dehydrogenation Tandem Reaction
Chen, Weiqiang,Li, Hui-Jing,Liu, Ying,Nan, Xiang,Wu, Yan-Chao,Zhang, Yin-Lin
supporting information, p. 3651 - 3666 (2019/09/30)
N -Sulfonyl- and N -acylpyrroles were synthesized via olefin ring-closing metathesis of diallylamines and in situ oxidative aromatization in the presence of the ruthenium Grubbs catalyst and a suitable copper catalyst. In the presence of Cu(OTf) 2/s
A facile synthesis of 1-aryl pyrroles by clauson-Kaas reaction using oxone as a catalyst under microwave irradiation
Gullapelli, Kumaraswamy,Brahmeshwari,Ravichander
, p. 143 - 148 (2019/03/21)
A new and efficient methodology to synthesize N-substituted pyrrole derivatives by Clauson Kaas reaction employing Oxone as catalyst was developed. The transformation was performed in acetonitrile under microwave irradiation. This procedure has several advantages such as high yield, clean product formation, and short reaction time.
Triflic acid controlled successive annelation of aromatic sulfonamides: an efficient one-pot synthesis of N-sulfonyl pyrroles, indoles and carbazoles
Abid, Mohammed,Teixeira, Liliana,T?r?k, Béla
, p. 4047 - 4050 (2008/02/02)
A novel one-pot synthesis of N-substituted heterocycles via successive cyclization/annelation starting from primary sulfonamides is described. This process directly leads to N-sulfonyl pyrroles, indoles and carbazoles. The selection of an appropriate reac
Efficient sulfonation of 1-phenylsulfonyl-1H-pyrroles and 1-phenylsulfonyl-1H-indoles using chlorosulfonic acid in acetonitrile
Janosik, Tomasz,Shirani, Hamid,Wahlstr?m, Niklas,Malky, Ilham,Stensland, Birgitta,Bergman, Jan
, p. 1699 - 1707 (2007/10/03)
The sulfonation of various 1-phenylsulfonyl-1H-pyrroles and 1-phenylsulfonyl-1H-indoles using chlorosulfonic acid in acetonitrile has been studied, leading to the development of a clean and operationally simple protocol allowing direct synthesis of the corresponding 1-phenylsulfonyl-1H-pyrrole-3- sulfonyl chlorides and 1-phenylsulfonyl-1H-indole-3-sulfonyl chlorides, respectively, both of which may be easily converted to various sulfonamide derivatives by treatment with nitrogen nucleophiles. Efficient and selective removal of the phenylsulfonyl- or tosyl groups in the sulfonamide series may be achieved under mild conditions.
1-arylsulfonyl-3-(α-hydroxybenzyl)-1H-pyrroles, a novel class of anti-HIV-1 reverse transcriptase inhibitors
Artico, Marino,Di Santo, Roberto,Costi, Roberta,Massa, Silvio,Scintu, Franca,Loi, Anna Giulia,De Montis, Antonella,La Colla, Paolo
, p. 1931 - 1936 (2007/10/03)
Various 1-arylsulfonyl-3-(α-hydroxybenzyl)-1H-pyrroles were prepared by Friedel-Crafts reaction of 1-arylsulfonyl-1H-pyrroles with aroylchlorides in the presence of aluminum trichloride, followed by reduction of the ketones to the required carbinols. The compounds were identified as a novel class of non-nucleoside HIV-1 reverse transcriptase inhibitors characterized by the presence of a diarylcarbinol moiety, a chemical feature that strictly correlates with the anti-HIV-1 activity.
