Bicyclic 5-5 Systems : two Heteroatoms 1:1

Kielty, Patrick and Aldabbagh, Fawaz (2020) Bicyclic 5-5 Systems : two Heteroatoms 1:1.


The four possible diheteropentalenes or bicyclic 5-5 ring-fused systems containing one non-bridgehead heteroatom in each ring are reviewed. Heteroatoms include oxygen, nitrogen, sulfur, selenium, tellurium, phosphorous, arsenic, antimony, and iodine. Fifteen new heterocyclic systems have been disclosed since 2008, although the reactions and synthesis of the pyrrolo[2,3-b]pyrrole system common in many natural products, including physostigmine, minfiensine, chimonanthine and psychotriasine, has attracted much attention. Reactions of conjugated and non-conjugated systems are described with many commencing from tryptamine and isosorbide. Highly conjugated adducts are considered in terms of aromaticity with several having semi-conductor properties.

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