Picoline sulfonation with

In yet another useful modification of this chemistry, Squibb chemists [34] devised a method for cyclization of 3-hydroxyvaline as required for the synthesis of the orally active monosulfactam tigemonam. Cyclization of the tertiary alcohol under typically employed conditions was problematic. Mitsunobu cyclization of 44 gave lactam 45 in poor yield along with an unprecedented rearrangement product 46 [35]. Mesylation was nonselective, but 0-sulfonation with picoline S03 complex followed by base treatment afforded 45 in 58% yield after recrystallization via the intermediacy of the derived sulfate. 

Interference with T4 absorption Cholestyramine, chromium picolinate, colestipol, ciprofloxacin, proton pump inhibitors, sucralfate, sodium polystyrene sulfonate, raloxifene, sevelamer hydrochloride, aluminum hydroxide, ferrous sulfate, calcium carbonate, bran, soy, coffee. 

For reactivity of complexes of pyridine, 2-picoline, and 2,6-lutidine with S03, see Floyd, D. M. Fritz, A. W. Pluscec, J. Weaver, E. R. Cimarusti, C. M. Monobactams. Preparation of (S)-3-Amino-2-oxoazetidine-l-sulfonic Acids from L-a-Amino-p-hydroxy Acids via Their Hydroxam-ic Esters. J. Org. Chem. 1982, 47,5160. 

Mercapto derivatives derived from 5-amino-2-picolinic acid (X-183) and S-aminonicotinic acid (X-184) are obtained by diazotization in the presence of sulfur and sodium sulfide. The thiols can be converted to the corresponding sulfonic acids with permanganate. ... 

Polymer-supported tetrabromooxomolybdate(V) was claimed to be a heterogeneous catalyst for alcohol oxidations with TBHP . However, it seems likely that molybdenum is leached from the surface and the observed catalysis may be, at least partially, homogeneous in nature. The same applies to Cr(III) and Ce(IV) catalysts supported on a perfluorinated sulfonic acid resin (Nafion K) which catalyze the oxidation of alcohols with TBHP . Similarly, vanadium-pillared montmorillonite clay (V-PILC) ° and a zeolite-encapsulated vanadium picolinate complex were shown to catalyze... 

During preparation of polyelectrolytes from poly(4-vinyl-pyridine) (P-4-VP) and alkyl halides, some puzzling phenomena were observed by Coleman and Fuoss. These authors found quaternization of pyridine, 4-picoline and 4-isopropylpyridine with n-butyl bromide in tetramethylene sulfone followed normal second-order kinetics. Similar results were reported by Hinshelwood and coworkersfor the reaction of pyridine and alkyl halides. However, on quaternization of poly(4-vinylpyridine) under the same conditions, they observed... 

The transformation from arenes into phenol acetates can be achieved with hypervalent iodine compounds (such as phenyliodonium acetate, PhI(OAc)2), with chromates, or under aerobic conditions. Ligands, like picolinic acids, stabilize the intermediate palladium(IV) salts. In the presence of Lewis acids or silver salts, biaryl formation takes place. The influence of different directing groups has recently been reviewed. For example, diaryl sulfones or sulfoxides having at least one heteroaryl attached can be oxidized to the corresponding aryl acetates (Scheme 5-194, Experimental Procedure below). ... 

Na-dichromate dihydrate added portionwise with stirring at 20-30° during ca. 0.5 hr. to a soln. of 3-picoline-4-sulfonic acid 1-oxide in coned. H2SO4, and allowed to react for 12 hrs. at the same temp. 3-carboxypyridine-4-sulfonic acid 1-oxide. Y 50-60%. - Direct oxidation of 3-picoline-4-sulfonic acid instead of its N-oxide gave poor results. J. Delarge, Farmaco, Ed. Sci. 22, 99 (1967). 

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