American Chemical Society
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Synthesis of 2‑Tetrazolylmethyl-isoindolin-1-ones via a One-Pot Ugi-Azide/(N-Acylation/exo-Diels–Alder)/Dehydration Process

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journal contribution
posted on 2016-11-30, 00:00 authored by Angel Rentería-Gómez, Alejandro Islas-Jácome, Alicia E. Cruz-Jiménez, Jessica C. Manzano-Velázquez, Susana Rojas-Lima, J. Oscar C. Jiménez-Halla, Rocío Gámez-Montaño
A series of fifteen 2-tetrazolylmethyl-isoindolin-1-one linked-type bis-heterocycles were synthesized in 10–76% yields under mild conditions via a one-pot Ugi-azide/(N-acylation/exo-Diels–Alder)/dehydration process from furan-2-ylmethanamine, aldehydes, isocyanides, azidotrimethylsilane, and maleic anhydride. Density functional theory calculations were performed using the polarizable continuum model (toluene)-M06-2X-D3/6-311+G­(d)//M06-2X-D3/6-31G­(d) level of theory to obtain the full energy profile when investigating over eight possible pathways. An anthracene-containing analogue displayed a distribution of its highest occupied molecular orbital–lowest unoccupied molecular orbital throughout both cyclic moieties.