Solidphase Synthesis of Heterocyclic Systems Heterocycles Containing One Heteroatom

Roland E. Dolle 22.1

Introduction

The synthesis of chemical libraries is now widely practiced in academic and industrial laboratories. The first examples of small-molecule libraries were collections of heterocycles, e.g. Ellman's 1,4-benzodiazepines and b-lactams from Affy-max. Of the 1250 libraries published since 1992, over 80% are based on a heterocyclic theme [1]. The impetus for the development and application of high-speed synthesis is tied to the pharmaceutical industry's quest for discovering new biologically active agents; heterocycles enjoy a rich history of providing leads for this multibillion dollar industry. This chapter presents a systematic examination of the solid-phase synthesis of heterocycles containing a single heteroatom. This treatise is organized by atom type (nitrogen, oxygen, sulfur), ring size, and degree of unsaturation. Table 22.1A-H lists the generic structures of all solid- and solution-phase heterocyclic libraries containing a single heteroatom that were published during 1992-2000.

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