Add time:08/31/2019         Source:sciencedirect.com

The chemistry of pyrimidines and their benzo derivatives, including quinazolines, perimidines and benzo[gh]perimidines is reviewed in this chapter, with particular attention paid to work published between 1996 and 2007, which covers the period since the publication of the second edition of Comprehensive Heterocyclic Chemistry. Fully aromatic, and both partially and fully reduced species are included, and oxo derivatives, including nucleosides and nucleotides are also covered. New routes to the synthesis of many of these heterocycles, as well as modern synthetic techniques, including microwave assisted procedures, are described. Both ring synthesis and substituent modification procedures are covered. The relative reactivity of different substituent groups and/or substituent positions is also discussed, including several examples of selective metal catalyzed cross-coupling reactions. Metal catalyzed amination and amidation reactions are also described. The importance of pyrimidine and quinazoline heterocyclic compounds in biological systems is also emphasized, since two of the four DNA bases are pyrimidine derivatives, and many modern pharmaceutical agents contain either pyrimidine or quinazoline fragments. Several examples of biologically important pyrimidine and quinazoline derivatives are identified, and in this context the signal transduction inhibitor imatinib (gleevec) is highlighted as one of the most significant new pyrimidine derivatives to have been identified in the last few years.

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