Quinoline-8-sulfonyl chloride

This group, used for intemucleotide protection, is introduced with 8-quinoline-sulfonyl chloride, [(CH3)2NC(S)S]2, and Ph, and is cleaved with BF3 (dioxane, H2O, rt). ... 

Methoxyquinoline reacts with a large excess of chlorosulfonic acid (10 equivalents) at 0-15 °C to give the 5-sulfonyl chloride. 8-Methoxy-5-quinoline-sulfonyl chloride is used as an analytical fluorogenic reagent for the chromatographic determination of amines, amino acids and peptides. ... 

Ref. [152] discusses the transformation of a dinucleoside pyrophosphate into a reactive azolide with an azole (e.g., 3-nitro-1,2,4-triazole or tetrazole). With quinoline-8-sulfonyl chloride the concomitantly formed phosphordiester can be converted back to the dinucleoside pyrophosphate (see scheme on the next page). 

Some 1,2-dihydroisoquinoline-l-ylphosphonates, e.g. (18), have been prepared from trialkyl phosphites, isoquinoline, and a sulfonyl chloride. Quinoline gave similarly the corresponding l,2-dihydroquinoline-2-ylphosphonates. The superbase (19) has been shown to be a very effective catalyst for the acylation of hindered and/or acid-sensitive alcohols with benzoic anhydride a P-acylated intermediate (20) was inferred from NMR data. 

Quinoline-2-carboxylic acid, 435 Quinoline-8-sulfonyl chloride, 435 8-Quinolinol, 19, 35 Quinone, 182-189, 191-193... 

While other more costly catalysts such as a variety of palladium salts also enabled direct 2-sulfonylation of the quinoline A/-oxides, the copper salts are more flexible and inexpensive. While a number of aryl sulfonyl chlorides coupled with quinoline N-oxides and isoquiniohne-AT-oxide, related compounds (N-oxides of pyridine and pyrazines) failed to react under these conditions. 

Quinolinesulfonyl hydrazides, useful as blood serum amine monooxidase inhibitors, are synthesised from the parent substituted quinolines via chlorosulfo-nation, achieved by treatment with excess chlorosulfonic acid and subsequent condensation of the sulfonyl chloride with hydrazine. ... 

Chatani recently reported that the reaction of aromatic amides that contain a 5-chloro-8-aminoquinoine moiety as the directing group with arylsulfonyl chlorides in the presence of Ni(OTf)2 as the catalyst results in sulfonylation at the ortho-position (Scheme 18) [46]. A blocking substituent, chloride, is required to avoid the sulfonylation at the quinoline ring at the 5-position. Various arylsulfonyl chlorides can be used as the coupling partner, as in 43-45. 

---