Sulfonamides are found in a number of commercially important compounds, and the synthesis of molecules containing a sulfonamide continues to be an important source of potential drug leads. Chemically, the sulfonamide group is known to strongly direct in ortho metalation reactions. Hence, under basic conditions nitrogen to carbon rearrangement of acyl groups from the nitrogen of the sulfonamide to the ortho position of the aromatic ring or to the ortho-tolyl position occurs leading to saccharin and homosachharin derivatives respectively. Similar reactivity is seen in the heteroaromatic series where rearrangement to the pyridine ring occurs. In the pyrimidine series formal extrusion of SO<sub>2</sub> leads to migration of the pyrimidine group to form unnatural 'quaternary' amino acids. This presentation will cover some of the recent work we have been conducting on this, and related, rearrangement chemistry.

Rearrangement chemistry of aryl and heteroaryl sulfonamides

253rd National Meeting (2017)

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