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

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...

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Published in:ACS omega 2016-11, Vol.1 (5), p.943-951
Main Authors: Rentería-Gómez, Angel, Islas-Jácome, Alejandro, Cruz-Jiménez, Alicia E, Manzano-Velázquez, Jessica C, Rojas-Lima, Susana, Jiménez-Halla, J. Oscar C, Gámez-Montaño, Rocío
Format: Article
Language:English
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Summary: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.
ISSN:2470-1343
2470-1343
DOI:10.1021/acsomega.6b00281