Scheme 3

The acid-labile carbamate linkage of type 2 was also applied to the parallel synthesis of a thiazolidinone library 12 according to Scheme 4. At the start of the synthesis, an excess of an unprotected symmetrical diamine was incorporated directly onto the carbonyl imidazole-ac-tivated support 1 to yield 9. Reaction with an aldehyde led to Schiff base 10, which was then reacted with mercaptosuccinic acid to heterocycle 11, the carboxyl function of which was used to introduce further diversity via amide formation. Cleavage from the support yielded finally the desired compounds of type 12 [15].

Application of trityl-based resins (see section for this reaction sequence was not possible as the trimethylorthoformate used for the preparation of the Schiff base resulted in poor swelling of the resin.



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