LINEAR ENCODING OF FUNCTIONAL GROUPS IN THE SYNTHESIS OF HETEROCYCLIC COMPOUNDS: CYCLOADDITION OF ENYNE AND ALKYNE UNITS

Abstract

A family of novel [4+2]-cycloaddition reactions is discussed to carry out efficient preparation of poly-substituted heterocyclic compounds in a single-step starting with linear precursors. High selectivity of the intramolecular transformation and pre-defined position of substituents in the product were governed by linear encoding in the structure of starting reagents. The designed reactions utilized green chemistry potential of cycloaddition approach and provided a convenient synthetic route to cyclopentapyridines, indoles, isoindoles, indolizines, isophosphindoles, benzofurans, benzothiophenes, benzoselenophenes (and corresponding dihydro derivatives).

Also published in Chemistry of Heterocyclic Compounds, 2012, 48 (1), pp 2-6

http://link.springer.com/article/10.1007/s10593-012-0959-5