Preparative Organic Chemistry
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ChemInform Abstract: Reaction of Chlorosulfonyl Isocyanate with Nitrones: An Efficient Method for the Synthesis of Cyclic Enamides and 2H-Pyrroles.
First published: January 10, 1989
Abstract
A series of nitrones such as (I) and (III), derived from cyclic conjugated ketones, is treated with chlorosulfonyl isocyanate according to A).
ChemInform Abstract
A series of nitrones such as (I) and (III), derived from cyclic conjugated ketones, is treated with chlorosulfonyl isocyanate according to A). In each case rearrangement takes place to give the corresponding cyclic amides. Treatment of the pyrrole 1-oxides (V) and (VII) with chlorosulfonyl isocyanate according to B) gives the 2H-pyrroles (VI) and (VIII) whereas the N-oxide (IX) furnishes the pyrrolidone (X). Plausible mechanisms for both types of reactions, i.e. rearrangement of N-methyl nitrones and conversion of pyrrole 1-oxides to pyrroles, are presented.
