Abstract
This chapter is devoted to recent progress in the chemistry of the 5:5 fused heterocyclic systems. There are four possible modes of 5:5 fusions of the simple five-membered heterocycles leading to four structures containing one heteroatom in each ring. The heteroatoms may be the same or different and may be O, NH, S, Se, Te, P, As, or Sb. The fully conjugated hetero analogs of pentalene dianion have a central C–C bond and are isoelectronic with the 10-π-electron pentalene dianion. The scope of the chapter is outlined with a survey of various structural types and nomenclature of the parent compounds and their derivatives. New synthetic procedures and synthetic applications of title compounds are presented. This review has concentrated on the new developments achieved from 1997 to September 2007.
Keywords
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Abbreviations
- Ac:
-
Acetyl;
- AIBN:
-
Azobis(isobutyronitrile);
- Boc:
-
tert-Butoxycarbonyl;
- Bn:
-
Benzyl;
- DBU:
-
1,8-Diazabicyclo[5.4.0]undec-7-ene;
- DCM:
-
Dichloromethane;
- DDQ:
-
2,3-Dichloro-5,6-dicyano-1,4-benzoquinone;
- DMAD:
-
Dimethyl acetylenedicarboxylate;
- DMAP:
-
4-Dimethylaminopyridine;
- DME:
-
Dimethoxyethane;
- DMF:
-
Dimethylformamide;
- DMSO:
-
Dimethylsulfoxide;
- DPPE:
-
1,2-Bis(diphenylphosphino)ethane;
- EWG:
-
Electron withdrawing group;
- LDA:
-
Lithium diisopropylamide;
- MCPBA:
-
m-Chloroperbenzoic acid;
- MW:
-
Microwave;
- NBS:
-
N-Bromosuccinimide;
- NPMI:
-
N-Phenylmaleimide;
- PPA:
-
Polyphosphoric acid;
- Ph:
-
Phenyl;
- TFA:
-
Trifluoroacetic acid;
- THF:
-
Tetrahydrofuran;
- TMS:
-
Trimethylsilyl;
- Tol:
-
Tolyl;
- Ts:
-
Tosyl
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Acknowledgements
The authors are grateful to the Slovak Grant Agency (VEGA No. 13549/06, No. 13584/06) and APVV (No. 20-000305).
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Krutosíková, A., Gracza, T. (2008). Recent Studies in Chemistry of Hetero Analogs of Pentalene Dianion. In: Topics in Heterocyclic Chemistry. Springer, Berlin, Heidelberg. https://doi.org/10.1007/7081_2008_3
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DOI: https://doi.org/10.1007/7081_2008_3
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