878376-34-2Relevant academic research and scientific papers
Unified Approach to Benzo[ d]thiazol-2-yl-Sulfonamides
Zále?ák, Franti?ek,Ková?, Ond?ej,Lachetová, Eli?ka,?t'astná, Nikola,Pospí?il, Ji?í
, p. 11291 - 11309 (2021/09/07)
In this paper, we report a unified approach to N-substituted and N,N-disubstituted benzothiazole (BT) sulfonamides. Our approach to BT-sulfonamides starts from simple commercially available building blocks (benzo[d]thiazole-2-thiol and primary and secondary amines) that are connected via (a) a S oxidation/S-N coupling approach, (b) a S-N coupling/S-oxidation sequence, or via (c) a S-oxidation/S-F bond formation/SuFEx approach. The labile N-H bond in N-monoalkylated BT-sulfonamides (pKa (BTSO2N(H)Bn) = 3.34 ± 0.05) further allowed us to develop a simple weak base-promoted N-alkylation method and a stereoselective microwave-promoted Fukuyama-Mitsunobu reaction. N-Alkyl-N-aryl BT-sulfonamides were accessed with the help of the Chan-Lam coupling reaction. Developed methods were further used in stereo and chemoselective transformations of podophyllotoxin and several amino alcohols.
PyFluor: A low-cost, stable, and selective deoxyfluorination reagent
Nielsen, Matthew K.,Ugaz, Christian R.,Li, Wenping,Doyle, Abigail G.
supporting information, p. 9571 - 9574 (2015/08/18)
We report an inexpensive, thermally stable deoxyfluorination reagent that fluorinates a broad range of alcohols without substantial formation of elimination side products. This combination of selectivity, safety, and economic viability enables deoxyfluorination on preparatory scale. We employ the [18F]-labeled reagent in the first example of a no-carrier-added deoxy-radiofluorination.
A convenient preparation of heteroaryl sulfonamides and sulfonyl fluorides from heteroaryl thiols
Wright, Stephen W.,Hallstrom, Kelly N.
, p. 1080 - 1084 (2007/10/03)
Heteroaromatic thiols may be oxidized to the sulfonyl chloride at low temperature (-25 °C) by using 3.3 equiv of aqueous sodium hypochlorite. The reaction is rapid, avoids the use of chlorine gas, and succeeds with substrates that have previously been found to afford little or none of the sulfonamide product with other procedures. The method allows the preparation of the sulfonyl fluorides, which are stable enough to be purified and stored, making them potentially useful monomers in parallel chemistry efforts.
