Linear encoding of functional groups in the synthesis of heterocyclic compounds: cycloaddition of enyne and alkyne units
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A family of novel [4 + 2] cycloaddition reactions is discussed for the efficient preparation of poly-substituted heterocyclic compounds in a single step starting with linear precursors. The high selectivity of the intramolecular transformation and the predefined position of the substituents in the product were governed by linear encoding in the structure of the starting reagents. The designed reactions utilized the green chemistry potential of the cycloaddition approach and provided a convenient synthetic route to cyclopentapyridines, indoles, isoindoles, indolizines, isophosphindoles, benzofurans, benzothiophenes, and benzoselenophenes (and corresponding dihydro derivatives).
Keywordsalkyne cyclic allene enyne cycloaddition cycloaromatization selectivity
- 6.M. Rubin, A. W. Sromek, and V. Gevorgyan, Synlett, 2265 (2003).Google Scholar