Issue 46, 2015

Iterative double cyclization reaction by SRN1 mechanism. A theoretical interpretation of the regiochemical outcome of diazaheterocycles

Abstract

In this report, we present a synthetic and mechanistic study of novel iterative double cyclization intramolecular SRN1 reactions from diamides bearing two aryl iodide moieties. This cyclization affords aromatic diazaheterocyclic compounds in good yields. Two synthetic strategies were employed for their preparation: intramolecular SRN1 and Homolytic Aromatic Substitution. The mechanism is non-trivial and we propose that radicals are intermediates. The regiochemistry was studied using computational calculations, employing the DFT method and the B3LYP functional. It was found that the distribution of products depends on the cyclization activation energies, proportion of neutral conformers, and the type of the electron transfer reaction.

Graphical abstract: Iterative double cyclization reaction by SRN1 mechanism. A theoretical interpretation of the regiochemical outcome of diazaheterocycles

Supplementary files

Article information

Article type
Paper
Submitted
15 Mar 2015
Accepted
13 Apr 2015
First published
13 Apr 2015

RSC Adv., 2015,5, 36374-36384

Author version available

Iterative double cyclization reaction by SRN1 mechanism. A theoretical interpretation of the regiochemical outcome of diazaheterocycles

L. E. Peisino, G. P. Camargo Solorzano, M. E. Budén and A. B. Pierini, RSC Adv., 2015, 5, 36374 DOI: 10.1039/C5RA04563K

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