Abstract: A summary is given of our results and literature data on the use of nitroarenes in pericyclic [4+2] and [3+2] cycloaddition reactions to give heterocycles fused with the original aromatic carbocycle. Highly electrophilic bicyclic nitroarenes, which are considered superelectrophiles, are capable of undergoing the Diels–Alder reaction with nucleophilic alkenes as C=C–N(O)=O heterodienes to give dihydro-1,2-oxazine N-oxides. Dinitrobenzenes, 1,3,5-trinitrobenzene, and their substituted derivatives and analogs as well as nitrobenzenes and 1,3-dinitrobenzenes fused with electron-withdrawing azoles and pyridine are capable of undergoing 1,3-dipolar cycloaddition as dipolarophiles at the C=C(NO2) bond with N-alkylazomethine ylides serving as 1,3-dipoles to give N-alkylpyrrolidines, pyrrolines, or pyrroles fused to an aromatic ring, depending on the structure of the nitro compound substrates. A relationship was found between the reactivity of the nitroarenes in pericyclic [4+2] and [3+2] cycloaddition reactions and the electrophilicity of these substrates.

Cite: Shevelev S.A. , Starosotnikov A.M.
Pericyclic [4+2] and [3+2] Cycloaddition Reactions of Nitroarenes in Heterocyclic Synthesis
Chemistry of Heterocyclic Compounds. 2013. V.49. N1. P.92-115. DOI: 10.1007/s10593-013-1233-1 WOS Scopus OpenAlex

Identifiers:

Web of science:	WOS:000318648700006
Scopus:	2-s2.0-84877633692
OpenAlex:	W1999718099

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OpenAlex	33
Scopus	32
Web of science	31

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