10.02 - Bicyclic 5-5 Systems: Three Heteroatoms 1:2

Add time:09/01/2019    Source:sciencedirect.com

This chapter reviews advances in the synthesis and reactivity of the bicyclic 5-5 heterocycles with 1:2-heteroatom orientation reported in the period 1995–2006, since the publication of CHEC-II(1996). New synthetic methods and improvements to older methods for the synthesis of these heterocycles are surveyed, highlighting current areas of application.To date, there are 55 reported fully conjugated variants with 18 examples of the unsubstituted parents known. Many of these are chemically robust and tolerate a wide variety of functional group manipulations to afford compounds of, in particular, biological interest.There are a great many structural variants reported of the nonconjugated bicyclic 5-5 heterocycles with 1:2-heteroatom orientation. Despite the topological similarity of many of the heterocycles covered in this chapter, the chemistry of the nonconjugated systems is diverse and the more interesting aspects of their synthesis and reactivity, rather than a comprehensive review, are given. In this chapter, particular focus is given to synthetic approaches based upon 1,3-dipolar cycloaddition methodology.

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